[sheet: Closing Checklist]

Item No.	Tab No.	Category	Document Description	Responsible Party	Delivery By	Target Date	Actual Date	Status	Notes
1	1.1	I. Underwriting Agreement & Ancillary	Underwriting Agreement (Execution Version, dated October 12, 2023) among Penterra Pharmaceuticals Corp., the Selling Stockholders (Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC), and the Underwriters (Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC)	Calderwood & Harkness LLP / Caldwell, Pearce & Strauss LLP	All Parties	10/12/2023	10/12/2023	Received	Executed at pricing; 6,250,000 shares at $41.60/share; 2.50% underwriting discount ($1.04/share); over-allotment option of 937,500 shares; governed by Delaware law
2	1.2	I. Underwriting Agreement & Ancillary	Underwriting Agreement — Compiled Executed Signature Pages (PPC by Lisa Hargrove, CFO; each Selling Stockholder; Ridgeline Securities LLC by Jonathan Pryce-Hall; Broadmark Capital Inc. by Samuel Okonkwo; Linden Groves & Co.; Harborview Partners LLC)	Calderwood & Harkness LLP	All Parties	10/12/2023	10/12/2023	Received	All counterparty signature pages compiled
3	1.3	I. Underwriting Agreement & Ancillary	Selling Stockholder Power of Attorney and Custody Agreement (executed by each Selling Stockholder appointing David Orenstein as attorney-in-fact; Pinnacle Trust & Transfer Co. as custodian)	Whitfield & Garza LLP	Selling Stockholders	10/12/2023	10/12/2023	Received	Dated October 12, 2023
4	1.4	I. Underwriting Agreement & Ancillary	New 90-Day Lock-Up Agreement (Secondary Offering) — executed by Selling Stockholders in favor of Ridgeline Securities LLC and Broadmark Capital Inc. as representatives of the underwriters; restricts disposition of retained shares for 90 days from closing (October 17, 2023), expiring January 15, 2024	Calderwood & Harkness LLP	Selling Stockholders	10/12/2023	10/12/2023	Received	Lock-up covers all shares retained post-offering
5	2.1	II. Registration / SEC Filings	Form S-3 Shelf Registration Statement (File No. 333-274851), declared effective August 22, 2023 — Base Prospectus	Calderwood & Harkness LLP	PPC	08/22/2023	08/22/2023	Received	Previously filed and effective
6	2.2	II. Registration / SEC Filings	Preliminary Prospectus Supplement (filed October 2, 2023)	Calderwood & Harkness LLP	PPC	10/02/2023	10/02/2023	Received	Filed with SEC
7	2.3	II. Registration / SEC Filings	Final Prospectus Supplement (Rule 424(b)(5) filing, dated October 12, 2023) — 6,250,000 shares of common stock (par value $0.001/share) at $41.60/share; CUSIP 70831X 10 5; Nasdaq: PNTR	Calderwood & Harkness LLP	PPC	10/12/2023	10/12/2023	Received	Filed pursuant to Rule 424(b)(5); CIK 0001987654
8	2.4	II. Registration / SEC Filings	Issuer Free Writing Prospectus — Pricing Term Sheet (filed pursuant to Rule 433, dated October 12, 2023)	Calderwood & Harkness LLP / Ridgeline Securities LLC	PPC / Underwriters	10/12/2023	10/12/2023	Received	Final pricing: $41.60/share; discount $1.04/share; net $40.56/share; settlement 10/17/2023
9	2.5	II. Registration / SEC Filings	Form 8-K — Current Report (Entry into Underwriting Agreement, dated October 12, 2023; Item 8.01)	Calderwood & Harkness LLP	PPC	10/12/2023	10/12/2023	Received	CIK 0001987654; EIN 82-4039571
10	2.6	II. Registration / SEC Filings	Section 16 Form 4 Filings for Dr. Elena Castellano (3,000,000 shares), Dr. Riccardo Castellano (2,500,000 shares), and Dr. Marco Castellano (500,000 shares)	Calderwood & Harkness LLP	PPC / Insiders	10/17/2023	10/17/2023	Received	Filed within 2 business days of closing per Section 16(a)
11	3.1	III. Lock-Up Waiver Documents	Lock-Up Waiver Request Letter — PPC to Ridgeline Securities LLC (dated September 18, 2023; requesting early release of 180-day lock-up effective October 12, 2023)	Calderwood & Harkness LLP	PPC (David Orenstein)	09/18/2023	09/18/2023	Received	IPO lock-up commenced April 17, 2023; natural expiration October 14, 2023; early release 2 days prior
12	3.2	III. Lock-Up Waiver Documents	Lock-Up Waiver Request Letter — PPC to Broadmark Capital Inc. (dated September 18, 2023; Attn: Samuel Okonkwo)	Calderwood & Harkness LLP	PPC (David Orenstein)	09/18/2023	09/18/2023	Received	Same terms as Ridgeline request
13	3.3	III. Lock-Up Waiver Documents	Lock-Up Waiver Request Letter — PPC to Morningstar Zanthor & Co. (dated September 18, 2023; Attn: Diane Chaudhary)	Calderwood & Harkness LLP	PPC (David Orenstein)	09/18/2023	09/18/2023	Received	Morningstar Zanthor is IPO co-manager; not participating in secondary syndicate
14	3.4	III. Lock-Up Waiver Documents	Lock-Up Waiver Consent — Ridgeline Securities LLC (executed September 29, 2023; signed by Jonathan Pryce-Hall; granting early release effective October 12, 2023)	Calderwood & Harkness LLP	Ridgeline Securities LLC	09/29/2023	09/29/2023	Received	Consent limited to shares sold in secondary offering
15	3.5	III. Lock-Up Waiver Documents	Lock-Up Waiver Consent — Broadmark Capital Inc. (executed September 29, 2023; signed by Samuel Okonkwo)	Calderwood & Harkness LLP	Broadmark Capital Inc.	09/29/2023	09/29/2023	Received	Consent limited to shares sold in secondary offering
16	3.6	III. Lock-Up Waiver Documents	Lock-Up Waiver Consent — Morningstar Zanthor & Co. (executed September 29, 2023; signed by Diane Chaudhary)	Calderwood & Harkness LLP	Morningstar Zanthor & Co.	09/29/2023	09/29/2023	Received	All three IPO underwriter consents now obtained; 14-day advance notice requirement waived by consent given de minimis 2-day gap
17	4.1	IV. Legal Opinions	Issuer's Counsel Legal Opinion — Calderwood & Harkness LLP (dated October 17, 2023; addressed to underwriters; re: valid issuance and due authorization of 6,250,000 shares of PPC common stock, par value $0.001/share; good standing in Delaware; no conflict with charter documents)	Calderwood & Harkness LLP (Jennifer Kwon)	Underwriters	10/17/2023	10/17/2023	Received	Signed by Jennifer Kwon, Responsible Partner
18	4.2	IV. Legal Opinions	Issuer's Counsel Negative Assurance Letter (10b-5 Letter) — Calderwood & Harkness LLP (dated October 17, 2023; addressed to underwriters; covering Final Prospectus Supplement and Base Prospectus under S-3, File No. 333-274851)	Calderwood & Harkness LLP	Underwriters	10/17/2023	10/17/2023	Received	Nothing came to attention of counsel re untrue statement or omission of material fact
19	5.1	V. Comfort Letters	Initial Comfort Letter — Graystone & Whitmore LLP (dated October 12, 2023; addressed to underwriters; covering financial statements and financial data in prospectus supplement)	Graystone & Whitmore LLP (Thomas Reiter)	Underwriters	10/12/2023	10/12/2023	Received	Request letter sent by Audrey Zhou on October 3, 2023
20	5.2	V. Comfort Letters	Bring-Down Comfort Letter — Graystone & Whitmore LLP (dated October 17, 2023; confirming no material changes from initial comfort letter as of closing date)	Graystone & Whitmore LLP (Thomas Reiter)	Underwriters	10/17/2023	10/17/2023	Received	Bring-down request sent October 15, 2023
21	6.1	VI. Officers' Certificates	Officer's Certificate of Penterra Pharmaceuticals Corp. (dated October 17, 2023; signed by Dr. Marco Castellano, CEO, and Lisa Hargrove, CFO; certifying accuracy of representations and warranties, compliance with covenants, and absence of material adverse change)	Calderwood & Harkness LLP	PPC	10/17/2023	10/17/2023	Received	Delivered at closing
22	6.2	VI. Officers' Certificates	Secretary's Certificate of Penterra Pharmaceuticals Corp. (dated October 17, 2023; signed by David Orenstein, General Counsel & Corporate Secretary; certifying incumbency of officers, attaching certificate of incorporation (as amended), bylaws, and board resolutions)	Calderwood & Harkness LLP	PPC (David Orenstein)	10/17/2023	10/17/2023	Received	Includes certified charter and bylaws
23	6.3	VI. Officers' Certificates	Board Resolutions of Penterra Pharmaceuticals Corp. (adopted September 8, 2023; authorizing cooperation with selling-stockholder secondary offering, Underwriting Agreement, prospectus supplement filings, officer's certificates, engagement of Calderwood & Harkness LLP, and payment of issuer expenses up to $765,000)	Calderwood & Harkness LLP	PPC	09/08/2023	09/08/2023	Received	Attached to Secretary's Certificate
24	7.1	VII. Selling Stockholder Deliverables	Selling Stockholder Representation Letter (dated October 12, 2023; from each Selling Stockholder to PPC and underwriters; re beneficial ownership, authority to sell, absence of encumbrances, accuracy of prospectus information, compliance with lock-up waiver terms)	Whitfield & Garza LLP (Patricia Velázquez)	Selling Stockholders	10/12/2023	10/12/2023	Received	Executed by Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC

25	7.2	VII. Selling Stockholder Deliverables	Selling Stockholder Certificate (dated October 17, 2023; executed by each Selling Stockholder or David Orenstein as attorney-in-fact; certifying representations and warranties remain true and correct as of closing; all conditions satisfied)	Whitfield & Garza LLP / Calderwood & Harkness LLP	Selling Stockholders	10/17/2023	10/17/2023	Received	Bring-down certification
26	8.1	VIII. Good Standing & Transfer Agent	Good Standing Certificate — Delaware Secretary of State (dated October 16, 2023; confirming Penterra Pharmaceuticals Corp. is in good standing under Delaware law)	Calderwood & Harkness LLP	PPC	10/16/2023	10/16/2023	Received	Transmitted under C&H cover memo
27	8.2	VIII. Good Standing & Transfer Agent	DTC Eligibility / Transfer Agent Direction Letter — Pinnacle Trust & Transfer Co. (dated October 16, 2023; signed by David Orenstein; instructing book-entry delivery of 6,250,000 shares through DTC for settlement on October 17, 2023; confirming DTC eligibility of PPC common stock, CUSIP 70831X 10 5)	Calderwood & Harkness LLP	PPC (David Orenstein) / Pinnacle Trust & Transfer Co.	10/16/2023	10/16/2023	Received	Pinnacle Trust & Transfer Co. at 1 Ashbury Asset Advisors Plaza, 30th Floor, New York, NY 10004
28	9.1	IX. Closing Documents & Correspondence	Closing Memorandum — Calderwood & Harkness LLP (dated October 17, 2023; summarizing settlement mechanics, wire of net proceeds of $253,500,000 to selling stockholders, underwriting commission allocation: Ridgeline $2,925,000 (45%), Broadmark $1,950,000 (30%), Linden Groves $975,000 (15%), Harborview $650,000 (10%); total $6,500,000)	Calderwood & Harkness LLP (Audrey Zhou / Brendan Walsh)	Working Group	10/17/2023	10/17/2023	Received	Funds flow confirmed
29	9.2	IX. Closing Documents & Correspondence	Closing Confirmation Email — Calderwood & Harkness LLP to Working Group (dated October 17, 2023; from Audrey Zhou confirming successful closing and settlement of 6,250,000 shares at $41.60/share; all deliverables received; funds disbursed)	Calderwood & Harkness LLP (Audrey Zhou)	Working Group	10/17/2023	10/17/2023	Received	Distributed to David Orenstein, Lisa Hargrove, Jonathan Pryce-Hall, Angela Ferris, Samuel Okonkwo, Margaret Hui, Ryan Petrosian, Patricia Velázquez
30	9.3	IX. Closing Documents & Correspondence	Closing Index and Document Binder Table of Contents	Calderwood & Harkness LLP (Brendan Walsh)	Working Group	10/27/2023	10/27/2023	Received	Final binder compiled upon matter close

[sheet: Summary]

Field	Detail
Matter	Penterra Pharmaceuticals Corp. — Selling Stockholder Secondary Offering
Issuer	Penterra Pharmaceuticals Corp. (Delaware corporation; Nasdaq: PNTR; CIK: 0001987654)
Issuer Address	400 Meridian Parkway, Suite 1200, Princeton, NJ 08540
Issuer's Counsel	Calderwood & Harkness LLP (One Liberty Plaza, 52nd Floor, New York, NY 10006)
Responsible Partner	Jennifer Kwon
Billing Partner	Theodore Langston
Lead Associate	Audrey Zhou
Working Associate	Brendan Walsh
Selling Stockholders	Dr. Elena Castellano (3,000,000 shares); Dr. Riccardo Castellano (2,500,000 shares); Dr. Marco Castellano (500,000 shares); Castellano Family Holdings LLC (250,000 shares)
Selling Stockholders' Counsel	Whitfield & Garza LLP (590 Madison Avenue, 28th Floor, New York, NY 10022) — Patricia Velázquez
Lead Left Book-Runner	Ridgeline Securities LLC (383 Madison Avenue, New York, NY 10017) — Jonathan Pryce-Hall / Angela Ferris
Joint Book-Runner	Broadmark Capital Inc. (200 Park Avenue, New York, NY 10166) — Samuel Okonkwo
Co-Managers	Linden Groves & Co. (745 Fifth Avenue, New York, NY 10151); Harborview Partners LLC (1 Federal Street, Boston, MA 02110)
Underwriters' Counsel	Caldwell, Pearce & Strauss LLP (1251 Avenue of the Americas, 40th Floor, New York, NY 10020) — Margaret Hui / Ryan Petrosian
IPO Lock-Up Parties (Waiver Grantors)	Ridgeline Securities LLC; Broadmark Capital Inc.; Morningstar Zanthor & Co. (600 Lexington Avenue, New York, NY 10022) — Diane Chaudhary
Auditors	Graystone & Whitmore LLP (30 Rockefeller Plaza, New York, NY 10112) — Thomas Reiter
Transfer Agent	Pinnacle Trust & Transfer Co. (1 Ashbury Asset Advisors Plaza, 30th Floor, New York, NY 10004)
Financial Printer	Apex Financial Printing Inc. (55 Water Street, New York, NY 10041)
D&O Insurer	Atlantic Omnivrel Insurance Co. (Stamford, CT)
Offering Type	Registered selling-stockholder secondary offering (follow-on); no primary shares; PPC receives no proceeds
Registration	Shelf takedown under Form S-3 (File No. 333-274851), declared effective August 22, 2023; Prospectus Supplement filed pursuant to Rule 424(b)(5)
Base Shares Offered	6,250,000 shares of common stock, par value $0.001/share
Over-Allotment Option	937,500 additional shares (15% of base); 30-day option from October 12, 2023; deadline November 11, 2023; over-allotment closing November 16, 2023
Public Offering Price	$41.60 per share

Aggregate Base Offering Value	$260,000,000
Maximum Offering Size (with OA)	~$299,000,000 (7,187,500 shares × $41.60)
Underwriting discount	2.50% ($1.04 per share); Total (base): $6,500,000
Net Proceeds to Selling Stockholders (base)	$253,500,000 ($40.56 per share × 6,250,000)
CUSIP	70831X 10 5
IPO Date / Lock-Up Commencement	April 17, 2023 (IPO price: $22.00/share)
Original IPO Lock-Up Expiration	October 14, 2023 (180 days from April 17, 2023)
Lock-Up Waiver Effective Date	October 12, 2023 (2 days early; solely for shares sold in secondary)
Lock-Up Waivers Received	September 29, 2023 (all three IPO underwriters)
New Secondary Lock-Up	90 days from closing (October 17, 2023); expiring January 15, 2024
Engagement Opened	September 5, 2023
Organizational Call	September 12, 2023
Preliminary Prospectus Supplement Filed	October 2, 2023
Road Show / Marketing	October 9–11, 2023
Pricing / UA Signing	October 12, 2023
Settlement / Closing (T+3)	October 17, 2023
Matter Closed	October 27, 2023
Shares Outstanding (PPC)	120,000,000
Market Cap (approx. 9/1/2023)	~$4.8 billion
Castellano Family Pre-Offering Holdings	40,100,000 shares (~33.4% of outstanding)
Castellano Family Post-Offering Holdings (base)	33,850,000 shares (~28.2% of outstanding)
Castellano Family Post-Offering Holdings (full OA)	32,912,500 shares (~27.4% of outstanding)
Issuer Expenses	$765,000 (Nasdaq listing $45,000; C&H legal fees $485,000; G&W accounting $175,000; Apex printing $35,000; Misc. $25,000)
Governing Law	State of Delaware
PPC EIN	82-4039571

CFH LLC EIN	87-2165438
Prepared By	Audrey Zhou and Brendan Walsh, Calderwood & Harkness LLP
Date Prepared	October 17, 2023 (updated through closing)

[sheet: Closing Checklist]
Item No. | Tab No. | Category | Document Description | Responsible Party | Delivery By | Target Date | Actual Date | Status | Notes
1 | 1.1 | I. Underwriting Agreement & Ancillary | Underwriting Agreement (Execution Version, dated October 12, 2023) among Penterra Pharmaceuticals Corp., the Selling Stockholders (Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC), and the Underwriters (Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC) | Calderwood & Harkness LLP / Caldwell, Pearce & Strauss LLP | All Parties | 10/12/2023 | 10/12/2023 | Received | Executed at pricing; 6,250,000 shares at $41.60/share; 2.50% underwriting discount ($1.04/share); over-allotment option of 937,500 shares; governed by Delaware law
2 | 1.2 | I. Underwriting Agreement & Ancillary | Underwriting Agreement — Compiled Executed Signature Pages (PPC by Lisa Hargrove, CFO; each Selling Stockholder; Ridgeline Securities LLC by Jonathan Pryce-Hall; Broadmark Capital Inc. by Samuel Okonkwo; Linden Groves & Co.; Harborview Partners LLC) | Calderwood & Harkness LLP | All Parties | 10/12/2023 | 10/12/2023 | Received | All counterparty signature pages compiled
3 | 1.3 | I. Underwriting Agreement & Ancillary | Selling Stockholder Power of Attorney and Custody Agreement (executed by each Selling Stockholder appointing David Orenstein as attorney-in-fact; Pinnacle Trust & Transfer Co. as custodian) | Whitfield & Garza LLP | Selling Stockholders | 10/12/2023 | 10/12/2023 | Received | Dated October 12, 2023
4 | 1.4 | I. Underwriting Agreement & Ancillary | New 90-Day Lock-Up Agreement (Secondary Offering) — executed by Selling Stockholders in favor of Ridgeline Securities LLC and Broadmark Capital Inc. as representatives of the underwriters; restricts disposition of retained shares for 90 days from closing (October 17, 2023), expiring January 15, 2024 | Calderwood & Harkness LLP | Selling Stockholders | 10/12/2023 | 10/12/2023 | Received | Lock-up covers all shares retained post-offering
5 | 2.1 | II. Registration / SEC Filings | Form S-3 Shelf Registration Statement (File No. 333-274851), declared effective August 22, 2023 — Base Prospectus | Calderwood & Harkness LLP | PPC | 08/22/2023 | 08/22/2023 | Received | Previously filed and effective
6 | 2.2 | II. Registration / SEC Filings | Preliminary Prospectus Supplement (filed October 2, 2023) | Calderwood & Harkness LLP | PPC | 10/02/2023 | 10/02/2023 | Received | Filed with SEC
7 | 2.3 | II. Registration / SEC Filings | Final Prospectus Supplement (Rule 424(b)(5) filing, dated October 12, 2023) — 6,250,000 shares of common stock (par value $0.001/share) at $41.60/share; CUSIP 70831X 10 5; Nasdaq: PNTR | Calderwood & Harkness LLP | PPC | 10/12/2023 | 10/12/2023 | Received | Filed pursuant to Rule 424(b)(5); CIK 0001987654
8 | 2.4 | II. Registration / SEC Filings | Issuer Free Writing Prospectus — Pricing Term Sheet (filed pursuant to Rule 433, dated October 12, 2023) | Calderwood & Harkness LLP / Ridgeline Securities LLC | PPC / Underwriters | 10/12/2023 | 10/12/2023 | Received | Final pricing: $41.60/share; discount $1.04/share; net $40.56/share; settlement 10/17/2023
9 | 2.5 | II. Registration / SEC Filings | Form 8-K — Current Report (Entry into Underwriting Agreement, dated October 12, 2023; Item 8.01) | Calderwood & Harkness LLP | PPC | 10/12/2023 | 10/12/2023 | Received | CIK 0001987654; EIN 82-4039571
10 | 2.6 | II. Registration / SEC Filings | Section 16 Form 4 Filings for Dr. Elena Castellano (3,000,000 shares), Dr. Riccardo Castellano (2,500,000 shares), and Dr. Marco Castellano (500,000 shares) | Calderwood & Harkness LLP | PPC / Insiders | 10/17/2023 | 10/17/2023 | Received | Filed within 2 business days of closing per Section 16(a)
11 | 3.1 | III. Lock-Up Waiver Documents | Lock-Up Waiver Request Letter — PPC to Ridgeline Securities LLC (dated September 18, 2023; requesting early release of 180-day lock-up effective October 12, 2023) | Calderwood & Harkness LLP | PPC (David Orenstein) | 09/18/2023 | 09/18/2023 | Received | IPO lock-up commenced April 17, 2023; natural expiration October 14, 2023; early release 2 days prior
12 | 3.2 | III. Lock-Up Waiver Documents | Lock-Up Waiver Request Letter — PPC to Broadmark Capital Inc. (dated September 18, 2023; Attn: Samuel Okonkwo) | Calderwood & Harkness LLP | PPC (David Orenstein) | 09/18/2023 | 09/18/2023 | Received | Same terms as Ridgeline request
13 | 3.3 | III. Lock-Up Waiver Documents | Lock-Up Waiver Request Letter — PPC to Morningstar Zanthor & Co. (dated September 18, 2023; Attn: Diane Chaudhary) | Calderwood & Harkness LLP | PPC (David Orenstein) | 09/18/2023 | 09/18/2023 | Received | Morningstar Zanthor is IPO co-manager; not participating in secondary syndicate
14 | 3.4 | III. Lock-Up Waiver Documents | Lock-Up Waiver Consent — Ridgeline Securities LLC (executed September 29, 2023; signed by Jonathan Pryce-Hall; granting early release effective October 12, 2023) | Calderwood & Harkness LLP | Ridgeline Securities LLC | 09/29/2023 | 09/29/2023 | Received | Consent limited to shares sold in secondary offering
15 | 3.5 | III. Lock-Up Waiver Documents | Lock-Up Waiver Consent — Broadmark Capital Inc. (executed September 29, 2023; signed by Samuel Okonkwo) | Calderwood & Harkness LLP | Broadmark Capital Inc. | 09/29/2023 | 09/29/2023 | Received | Consent limited to shares sold in secondary offering
16 | 3.6 | III. Lock-Up Waiver Documents | Lock-Up Waiver Consent — Morningstar Zanthor & Co. (executed September 29, 2023; signed by Diane Chaudhary) | Calderwood & Harkness LLP | Morningstar Zanthor & Co. | 09/29/2023 | 09/29/2023 | Received | All three IPO underwriter consents now obtained; 14-day advance notice requirement waived by consent given de minimis 2-day gap
17 | 4.1 | IV. Legal Opinions | Issuer's Counsel Legal Opinion — Calderwood & Harkness LLP (dated October 17, 2023; addressed to underwriters; re: valid issuance and due authorization of 6,250,000 shares of PPC common stock, par value $0.001/share; good standing in Delaware; no conflict with charter documents) | Calderwood & Harkness LLP (Jennifer Kwon) | Underwriters | 10/17/2023 | 10/17/2023 | Received | Signed by Jennifer Kwon, Responsible Partner
18 | 4.2 | IV. Legal Opinions | Issuer's Counsel Negative Assurance Letter (10b-5 Letter) — Calderwood & Harkness LLP (dated October 17, 2023; addressed to underwriters; covering Final Prospectus Supplement and Base Prospectus under S-3, File No. 333-274851) | Calderwood & Harkness LLP | Underwriters | 10/17/2023 | 10/17/2023 | Received | Nothing came to attention of counsel re untrue statement or omission of material fact
19 | 5.1 | V. Comfort Letters | Initial Comfort Letter — Graystone & Whitmore LLP (dated October 12, 2023; addressed to underwriters; covering financial statements and financial data in prospectus supplement) | Graystone & Whitmore LLP (Thomas Reiter) | Underwriters | 10/12/2023 | 10/12/2023 | Received | Request letter sent by Audrey Zhou on October 3, 2023
20 | 5.2 | V. Comfort Letters | Bring-Down Comfort Letter — Graystone & Whitmore LLP (dated October 17, 2023; confirming no material changes from initial comfort letter as of closing date) | Graystone & Whitmore LLP (Thomas Reiter) | Underwriters | 10/17/2023 | 10/17/2023 | Received | Bring-down request sent October 15, 2023
21 | 6.1 | VI. Officers' Certificates | Officer's Certificate of Penterra Pharmaceuticals Corp. (dated October 17, 2023; signed by Dr. Marco Castellano, CEO, and Lisa Hargrove, CFO; certifying accuracy of representations and warranties, compliance with covenants, and absence of material adverse change) | Calderwood & Harkness LLP | PPC | 10/17/2023 | 10/17/2023 | Received | Delivered at closing
22 | 6.2 | VI. Officers' Certificates | Secretary's Certificate of Penterra Pharmaceuticals Corp. (dated October 17, 2023; signed by David Orenstein, General Counsel & Corporate Secretary; certifying incumbency of officers, attaching certificate of incorporation (as amended), bylaws, and board resolutions) | Calderwood & Harkness LLP | PPC (David Orenstein) | 10/17/2023 | 10/17/2023 | Received | Includes certified charter and bylaws
23 | 6.3 | VI. Officers' Certificates | Board Resolutions of Penterra Pharmaceuticals Corp. (adopted September 8, 2023; authorizing cooperation with selling-stockholder secondary offering, Underwriting Agreement, prospectus supplement filings, officer's certificates, engagement of Calderwood & Harkness LLP, and payment of issuer expenses up to $765,000) | Calderwood & Harkness LLP | PPC | 09/08/2023 | 09/08/2023 | Received | Attached to Secretary's Certificate
24 | 7.1 | VII. Selling Stockholder Deliverables | Selling Stockholder Representation Letter (dated October 12, 2023; from each Selling Stockholder to PPC and underwriters; re beneficial ownership, authority to sell, absence of encumbrances, accuracy of prospectus information, compliance with lock-up waiver terms) | Whitfield & Garza LLP (Patricia Velázquez) | Selling Stockholders | 10/12/2023 | 10/12/2023 | Received | Executed by Dr. Elena Castellano, Dr. Riccardo Castellano, Dr. Marco Castellano, and Castellano Family Holdings LLC
25 | 7.2 | VII. Selling Stockholder Deliverables | Selling Stockholder Certificate (dated October 17, 2023; executed by each Selling Stockholder or David Orenstein as attorney-in-fact; certifying representations and warranties remain true and correct as of closing; all conditions satisfied) | Whitfield & Garza LLP / Calderwood & Harkness LLP | Selling Stockholders | 10/17/2023 | 10/17/2023 | Received | Bring-down certification
26 | 8.1 | VIII. Good Standing & Transfer Agent | Good Standing Certificate — Delaware Secretary of State (dated October 16, 2023; confirming Penterra Pharmaceuticals Corp. is in good standing under Delaware law) | Calderwood & Harkness LLP | PPC | 10/16/2023 | 10/16/2023 | Received | Transmitted under C&H cover memo
27 | 8.2 | VIII. Good Standing & Transfer Agent | DTC Eligibility / Transfer Agent Direction Letter — Pinnacle Trust & Transfer Co. (dated October 16, 2023; signed by David Orenstein; instructing book-entry delivery of 6,250,000 shares through DTC for settlement on October 17, 2023; confirming DTC eligibility of PPC common stock, CUSIP 70831X 10 5) | Calderwood & Harkness LLP | PPC (David Orenstein) / Pinnacle Trust & Transfer Co. | 10/16/2023 | 10/16/2023 | Received | Pinnacle Trust & Transfer Co. at 1 Ashbury Asset Advisors Plaza, 30th Floor, New York, NY 10004
28 | 9.1 | IX. Closing Documents & Correspondence | Closing Memorandum — Calderwood & Harkness LLP (dated October 17, 2023; summarizing settlement mechanics, wire of net proceeds of $253,500,000 to selling stockholders, underwriting commission allocation: Ridgeline $2,925,000 (45%), Broadmark $1,950,000 (30%), Linden Groves $975,000 (15%), Harborview $650,000 (10%); total $6,500,000) | Calderwood & Harkness LLP (Audrey Zhou / Brendan Walsh) | Working Group | 10/17/2023 | 10/17/2023 | Received | Funds flow confirmed
29 | 9.2 | IX. Closing Documents & Correspondence | Closing Confirmation Email — Calderwood & Harkness LLP to Working Group (dated October 17, 2023; from Audrey Zhou confirming successful closing and settlement of 6,250,000 shares at $41.60/share; all deliverables received; funds disbursed) | Calderwood & Harkness LLP (Audrey Zhou) | Working Group | 10/17/2023 | 10/17/2023 | Received | Distributed to David Orenstein, Lisa Hargrove, Jonathan Pryce-Hall, Angela Ferris, Samuel Okonkwo, Margaret Hui, Ryan Petrosian, Patricia Velázquez
30 | 9.3 | IX. Closing Documents & Correspondence | Closing Index and Document Binder Table of Contents | Calderwood & Harkness LLP (Brendan Walsh) | Working Group | 10/27/2023 | 10/27/2023 | Received | Final binder compiled upon matter close
[sheet: Summary]
Field | Detail
Matter | Penterra Pharmaceuticals Corp. — Selling Stockholder Secondary Offering
Issuer | Penterra Pharmaceuticals Corp. (Delaware corporation; Nasdaq: PNTR; CIK: 0001987654)
Issuer Address | 400 Meridian Parkway, Suite 1200, Princeton, NJ 08540
Issuer's Counsel | Calderwood & Harkness LLP (One Liberty Plaza, 52nd Floor, New York, NY 10006)
Responsible Partner | Jennifer Kwon
Billing Partner | Theodore Langston
Lead Associate | Audrey Zhou
Working Associate | Brendan Walsh
Selling Stockholders | Dr. Elena Castellano (3,000,000 shares); Dr. Riccardo Castellano (2,500,000 shares); Dr. Marco Castellano (500,000 shares); Castellano Family Holdings LLC (250,000 shares)
Selling Stockholders' Counsel | Whitfield & Garza LLP (590 Madison Avenue, 28th Floor, New York, NY 10022) — Patricia Velázquez
Lead Left Book-Runner | Ridgeline Securities LLC (383 Madison Avenue, New York, NY 10017) — Jonathan Pryce-Hall / Angela Ferris
Joint Book-Runner | Broadmark Capital Inc. (200 Park Avenue, New York, NY 10166) — Samuel Okonkwo
Co-Managers | Linden Groves & Co. (745 Fifth Avenue, New York, NY 10151); Harborview Partners LLC (1 Federal Street, Boston, MA 02110)
Underwriters' Counsel | Caldwell, Pearce & Strauss LLP (1251 Avenue of the Americas, 40th Floor, New York, NY 10020) — Margaret Hui / Ryan Petrosian
IPO Lock-Up Parties (Waiver Grantors) | Ridgeline Securities LLC; Broadmark Capital Inc.; Morningstar Zanthor & Co. (600 Lexington Avenue, New York, NY 10022) — Diane Chaudhary
Auditors | Graystone & Whitmore LLP (30 Rockefeller Plaza, New York, NY 10112) — Thomas Reiter
Transfer Agent | Pinnacle Trust & Transfer Co. (1 Ashbury Asset Advisors Plaza, 30th Floor, New York, NY 10004)
Financial Printer | Apex Financial Printing Inc. (55 Water Street, New York, NY 10041)
D&O Insurer | Atlantic Omnivrel Insurance Co. (Stamford, CT)
Offering Type | Registered selling-stockholder secondary offering (follow-on); no primary shares; PPC receives no proceeds
Registration | Shelf takedown under Form S-3 (File No. 333-274851), declared effective August 22, 2023; Prospectus Supplement filed pursuant to Rule 424(b)(5)
Base Shares Offered | 6,250,000 shares of common stock, par value $0.001/share
Over-Allotment Option | 937,500 additional shares (15% of base); 30-day option from October 12, 2023; deadline November 11, 2023; over-allotment closing November 16, 2023
Public Offering Price | $41.60 per share
Aggregate Base Offering Value | $260,000,000
Maximum Offering Size (with OA) | ~$299,000,000 (7,187,500 shares × $41.60)
Underwriting discount | 2.50% ($1.04 per share); Total (base): $6,500,000
Net Proceeds to Selling Stockholders (base) | $253,500,000 ($40.56 per share × 6,250,000)
CUSIP | 70831X 10 5
IPO Date / Lock-Up Commencement | April 17, 2023 (IPO price: $22.00/share)
Original IPO Lock-Up Expiration | October 14, 2023 (180 days from April 17, 2023)
Lock-Up Waiver Effective Date | October 12, 2023 (2 days early; solely for shares sold in secondary)
Lock-Up Waivers Received | September 29, 2023 (all three IPO underwriters)
New Secondary Lock-Up | 90 days from closing (October 17, 2023); expiring January 15, 2024
Engagement Opened | September 5, 2023
Organizational Call | September 12, 2023
Preliminary Prospectus Supplement Filed | October 2, 2023
Road Show / Marketing | October 9–11, 2023
Pricing / UA Signing | October 12, 2023
Settlement / Closing (T+3) | October 17, 2023
Matter Closed | October 27, 2023
Shares Outstanding (PPC) | 120,000,000
Market Cap (approx. 9/1/2023) | ~$4.8 billion
Castellano Family Pre-Offering Holdings | 40,100,000 shares (~33.4% of outstanding)
Castellano Family Post-Offering Holdings (base) | 33,850,000 shares (~28.2% of outstanding)
Castellano Family Post-Offering Holdings (full OA) | 32,912,500 shares (~27.4% of outstanding)
Issuer Expenses | $765,000 (Nasdaq listing $45,000; C&H legal fees $485,000; G&W accounting $175,000; Apex printing $35,000; Misc. $25,000)
Governing Law | State of Delaware
PPC EIN | 82-4039571
CFH LLC EIN | 87-2165438
Prepared By | Audrey Zhou and Brendan Walsh, Calderwood & Harkness LLP
Date Prepared | October 17, 2023 (updated through closing)

[sheet: Closing Checklist]

Record

Parties

Dates

Amounts