Liabilities, Convertible Preferred Stock and Stockholders' (Deficit) Equity | 10. Liabilities, Convertible Preferred Stock and Stockholders' (Deficit) Equity Registered Direct Offering In May 2022, the Company issued and sold 10,752,688 shares of common stock at an offering price of $ 1.60 per share and pre-funded warrants to purchase up to 17,372,312 shares of common stock at an offering price of $ 1.5999 per warrant (representing the price per share of common stock sold in the offering minus the $ 0.0001 exercise price per warrant) in a registered direct offering pursuant to a shelf registration statement on Form S-3. The net proceeds to the Company from this offering were approximately $ 42.9 million, after deducting placement agent fees and offering costs of $ 2.1 million. Pre-Funded Warrants In February 2019, April 2020 and May 2022, the Company issued pre-funded warrants to purchase the Company’s common stock in underwritten public offerings at the offering price of the common stock, less the $ 0.0001 per share exercise price of each warrant. The warrants were recorded as a component of stockholders’ (deficit) equity within additional paid-in capital and have no expiration date. Per the terms of the warrant agreements, the outstanding warrants to purchase shares of common stock may not be exercised if the holder’s ownership of the Company’s common stock would exceed 4.99 % (“Maximum Ownership Percentage”), or 9.99 % for certain holders. By written notice to the Company, each holder may increase or decrease the Maximum Ownership Percentage to any other percentage (not in excess of 19.99 % for the majority of such warrants). The revised Maximum Ownership Percentage would be effective 61 days after the notice is received by the Company. As of June 30, 2023, the following pre-funded warrants for common stock were issued and outstanding: Issue Date Expiration Date Exercise Price Number of Warrants Outstanding February 8, 2019 None $ 0.0001 — April 30, 2020 None $ 0.0001 — May 20, 2022 None $ 0.0001 13,281,250 Total pre-funded warrants 13,281,250 As of August 4, 2023, an additional 7,031,250 pre-funded warrants have been exercised. Stock-Based Compensation 2016 Equity Incentive Plan The 2016 Equity Incentive Plan (“2016 Plan”) provides for an automatic increase in the number of shares reserved for issuance thereunder on January 1 of each year for the remaining term of the plan (through 2028) equal to (a) 4.0 % of the number of issued and outstanding shares of common stock on December 31 of the immediately preceding year, or (b) a lesser amount as approved by the Company’s board of directors each year. As a result of this provision, on January 1, 2023 and January 1, 2022, an additional 2,614,013 and 1,974,205 shares, respectively, became available for issuance under the 2016 Plan. In July 2020, the Company granted 228,200 restricted stock units ("RSUs"), to certain employees, with vesting terms subject to regulatory, commercial, and clinical milestones, in addition to a service condition. As of June 30, 2023, none of these RSUs had vested and all RSUs were forfeited since the performance milestones were not met within the required time frame. No stock-based compensation expense was recognized on these awards. On June 22, 2023, concurrent with the closing of the Asset Acquisition, the Company’s board of directors approved an amendment of the 2016 Plan to eliminate the per-participant annual award limits originally intended to comply with the qualified performance-based compensation exception set forth in Section 162(m) of the Internal Revenue Code, in light of the repeal of such exception pursuant to the Tax Cuts and Jobs Act of 2017. In addition, the Company approved 68,000,955 options contingent on stockholder approval to certain members of the board of directors, legacy Aeglea employees and consultants under the 2016 Plan. These awards are in excess of the shares available for issuance under the 2016 Plan and require stockholder approval before being granted. Accordingly, no expense has been recognized on these contingent awards since they are contingent on stockholder approval. As of June 30, 2023 , the 2016 Plan had 5,384,315 shares available for future issuance. 2018 Equity Inducement Plan On June 22, 2023, the Company's board of directors approved an increase of 70,000,000 in the number of shares reserved for issuance to the 2018 Equity Inducement Plan and granted 63,417,415 inducement awards to new hires. The grant-date fair value of these inducement awards will be recognized as expense on a pro-rata basis over the vesting period. The awards have an exercise price of $ 0.30 per option, vest ratably over four years , and have a ten-year exercise period from the grant date. Spyre 2023 Equity Incentive Plan On June 22, 2023, in connection with the Asset Acquisition, the Company assumed the Amended and Restated Spyre 2023 Equity Incentive Plan (the "Spyre Equity Plan") and its outstanding and unexercised stock options which were converted to options to purchase 68,365 shares of Aeglea common stock. The acquisition-date fair value of these grants will be recognized as an expense on a pro-rata basis over the vesting period. Parapyre Option Obligation On June 22, 2023, in connection with the Asset Acquisition, the Company assumed the Parapyre Option Obligation which provided for an annual equity grant of options to purchase 1 % of the then outstanding shares of Spyre's common stock, on a fully diluted basis, on the last business day of each calendar year during the term of the Paragon Agreement, at the fair market value determined by the board of directors of Spyre. As a result of the Asset Acquisition the Parapyre Option Obligation shall continue and Parapyre shall be entitled to receive the equivalent shares of the Company with the same terms. As of June 30, 2023, the pro-rated estimated fair value of the options to be granted on December 31, 2023, was approximately $ 0.3 million, of which $ 0.1 million was recognized as part of the liabilities assumed with the Asset Acquisition. For the three and six months ended June 30, 2023, $ 0.2 million was recognized as stock compensation expense related to the Parapyre Option Obligation. As of June 30, 2023, the unamortized expense related to the Parapyre Option Obligation was $ 1.3 million. The following table summarizes the Company’s stock awards granted under all plans for each of the periods indicated: Three Months Ended June 30, 2023 2022 Grants Weighted Average Grant Date Fair Value Grants Weighted Average Grant Date Fair Value Stock options 63,417,415 $ 0.30 429,000 $ 0.96 2016 Employee Stock Purchase Plan Under the Company’s 2016 Employee Stock Purchase Plan (“2016 ESPP”), the Company issued and sold 44,816 shares for aggregate cash proceeds of less than $ 0.1 million during the six months ended June 30, 2023. There were 64,743 shares issued and sold under the 2016 ESPP for aggregate cash proceeds of $ 0.2 million during the six months ended June 30, 2022. Stock-based Compensation Expense Total stock-based compensation expense related to all plans was as follows (in thousands): Three Months Ended Six Months Ended June 30, June 30, 2023 2022 2023 2022 Research and development $ 394 $ 691 $ 1,171 $ 1,392 General and administrative 1,517 1,327 2,449 2,726 Total stock-based compensation expense $ 1,911 $ 2,018 $ 3,620 $ 4,118 The following table summarizes the weighted-average Black-Scholes option pricing model assumptions used to estimate the fair value of stock options granted under the Company’s 2016 Plan, and the shares purchasable under the 2016 ESPP during the periods presented: Three Months Ended Six Months Ended June 30, June 30, 2023 2022 2023 2022 2016 Plan Expected term (in years) 6.03 5.98 6.03 6.01 Expected volatility 117 % 82 % 115 % 82 % Risk-free interest 3.98 % 2.96 % 3.99 % 2.07 % Dividend yield — — — — 2016 ESPP Expected term (in years) — — 0.49 0.49 Expected volatility — — 181 % 76 % Risk-free interest — — 4.99 % 1.09 % Dividend yield — — — — |