Stockholders' Equity | 6 . Stockholders’ Equity Amended and Restated Articles of Incorporation On May 25, 2021, the Company’s certificate of incorporation was amended and restated to authorize 120,000,000 shares of common stock and 5,000,000 shares of undesignated preferred stock, each with a par value of $0.001 per share. Securities Purchase Agreements and In May 2020, the Company entered into a Securities Purchase Agreement (the “May Purchase Agreement”) with several institutional and individual investors for the concurrent sale of: (i) 1,943,636 shares of the Company’s common stock in a registered direct offering, resulting in net proceeds of $4.4 million, after deducting the placement agent’s cash commissions and other offering expenses, and excluding the proceeds, if any, from the exercise of the warrants, and (ii) unregistered warrants to purchase up to an aggregate of 971,818 shares of common stock. The combined purchase price for one share and one warrant to purchase half of a share of common stock was $2.5725. In addition, the Company issued shares of stock at per share May 21, 2025 An investor participating in the transaction included an entity affiliated with David F. Hale, the chairman of the Company’s board of directors. In July 2020, the Company entered into a Securities Purchase Agreement (the “July Purchase Agreement”) with several institutional and individual investors for the concurrent sale of: (i) 2,581,867 shares of the Company’s common stock in a registered direct offering, resulting in net proceeds of $5.7 million, after deducting the placement agent’s cash commissions and other offering expenses, and excluding the proceeds, if any, from the exercise of the warrants, and (ii) unregistered warrants to purchase up to an aggregate of 1,290,933 shares of common stock. The combined purchase price for one share and one warrant to purchase half of a share of common stock was $ 2.3825 . The warrants issued to investors were, subject to certain ownership limitations, immediately exercisable at an exercise price equal to $ 2.32 per share and expire on January 21, 2026 . In addition, the Company issued warrants to purchase 154,912 shares of common stock at an exercise price of $ 2.9781 per share to the placement agent as part of its compensation, which warrants were immediately exercisable upon issuance and terminate on July 21, 2025 . Other investors participating in the July Purchase Agreement included an entity affiliated with SPH USA, and Daniel L. Kisner, a member of the Company’s board of directors. In August 2020, the Company entered into an underwriting agreement (as amended and restated, the “August Underwriting Agreement”) with Wainwright for the sale of 2,428,886 shares of the Company’s common stock at a price to the public of $2.10 per share, resulting in net proceeds of $4.4 million, after deducting the underwriter’s discounts, commissions and other offering expenses. In addition, the Company issued warrants to purchase 145,733 shares of common stock at an exercise price of $2.625 per share to Wainwright as part of its compensation, which warrants were immediately exercisable upon issuance and terminate on August 27, 2025. An investor participating in the transaction included Michael G. Carter, a member of the Company’s board of directors. In November 2020, the Company entered into an underwriting agreement (as amended and restated, the “November Underwriting Agreement”) with Wainwright for the sale of 7,258,065 shares of the Company’s common stock at a price to the public of $3.10 per share, resulting in net proceeds of $20.4 million, after deducting the underwriter’s discounts, commissions and other offering expenses. In addition, the Company issued warrants to purchase 435,484 shares of common stock at an exercise price of $3.875 per share to Wainwright as part of its compensation, which warrants were immediately exercisable upon issuance and terminate on November 17, 2025 In December 2020, the Company entered into an underwriting agreement (as amended and restated, the “December Underwriting Agreement”) with Wainwright for the sale of 19,161,667 shares of the Company’s common stock at a price to the public of $4.50 per share, resulting in net proceeds of $79.0 million, after deducting the underwriter’s discounts, commissions and other offering expenses In addition, the Company issued warrants to purchase 1,149,700 shares of common stock at an exercise price of $5.625 per share to Wainwright as part of its compensation, which warrants were immediately exercisable upon issuance and terminate on December 9, 2025 In connection with the May Purchase Agreement and July Purchase Agreement, the Company also agreed, on a best-efforts basis, to: (i) maintain its listing on The Nasdaq Capital Market to provide for the resale of the shares of common stock issuable upon the exercise of the warrants, and (ii) not enter into any agreement for the issuance of any shares of common stock involving a variable rate transaction before July 21, 2021, which expired in 2021 In December 2021, the Company executed an at-the-market (“ATM”) facility of up to $50.0 million. Common Stock Warrants A summary of warrant activity and changes in warrants outstanding is presented below: Number of Shares Underlying Warrants Weighted-Average Exercise Price per Share Weighted-Average Remaining Contractual Term Balance Outstanding - December 31, 2019 841,424 $ 37.97 2.75 Issued 4,265,198 $ 3.47 Exercised (74,781 ) $ 3.22 — Balance Outstanding - December 31, 2020 5,031,841 $ 9.25 4.40 Issued — $ — — Exercised (796,931 ) $ 2.56 — Balance Outstanding - December 31, 2021 4,234,910 $ 10.50 3.31 As of December 31, 2021 and 2020, all warrants met the criteria for classification in stockholders’ equity. Equity Incentive Plans Contemporaneous with the Merger closing: (i) Private Oncternal’s 2015 Equity Incentive Plan, as amended (the “2015 Plan”) was assumed by the Company, and (ii) the Company adopted the 2019 Incentive Award Plan (“2019 Plan”) under which the sum of: (a) 1,678,571 shares of common stock, (b) 275,579 shares of common stock previously outstanding under the GTx 2013 Equity Incentive Plan that were cancelled became available for issuance under the 2019 Plan, and (c) an annual increase on the first day of each calendar year beginning January 1, 2020, and ending on and including January 1, 2029, equal to the lesser of (A) 5% of the aggregate number of shares of common stock outstanding on the final day of the immediately preceding calendar year and (B) such smaller number of shares of common stock as is determined by the Board, are reserved for issuance. At December 31, 2021, 1,842,432 In July 2015, Private Oncternal adopted the 2015 Plan which provided for the issuance of up to 631,120 shares of common stock for incentive stock options, non-statutory stock options, restricted stock awards, restricted stock unit awards and other stock awards to its employees, members of its board of directors and consultants. In general, the options issued under the 2015 Plan expire ten years from the date of grant and vest over a four-year The 2019 Plan provides for the issuance of shares of common stock for incentive stock options, non-statutory stock options, restricted stock awards, restricted stock unit awards and other stock awards to its employees, members of its board of directors and consultants. In general, the stock options issued under the 2019 Plan expire ten years from the date of grant and vest over a four-year period. Certain stock option grants vest based on the achievement of development or regulatory milestones. The 2019 Plan allows for the early exercise of all stock option grants if authorized by the board of directors at the time of grant. On February 11, 2021, the Company’s board of directors adopted the 2021 Employment Inducement Incentive Award Plan (the “Inducement Plan”). The Inducement Plan is a non-shareholder approved stock plan adopted pursuant to the “inducement exception” provided under Nasdaq listing rules. The Inducement Plan is used exclusively for the issuance of non-statutory stock options to certain new hires who satisfied the requirements to be granted inducement grants under Nasdaq rules as an inducement material to the individual’s entry into employment with the Company. The terms of the Inducement Plan are substantially similar to the terms of our 2019 Plan. As amended on May 25, 2021 and December 16, 2021, the Company has reserved 2,800,000 shares of common stock under the Inducement Plan. A summary of the Company’s stock option activity under the 2015 Plan, 2019 Plan and Inducement Plan is as follows: Number of Options Weighted- Average Exercise Price Weighted- Average Remaining Contractual Term (in years) Aggregate Intrinsic Value Outstanding at December 31, 2020 2,107,625 $ 4.08 Granted 4,884,800 $ 5.78 Cancelled (439,684 ) $ 5.46 Exercised (107,997 ) $ 3.84 Outstanding at December 31, 2021 6,444,744 $ 5.28 8.7 $ 613,190 Vested and exercisable at December 31, 2021 1,440,122 $ 3.92 6.8 $ 488,187 The weighted average grant date fair value per share of option grants for the years ended December 31, 2021 and 2020 was $4.35 and $2.53 per share, respectively. The intrinsic value is calculated as the difference between the fair value of the Company’s common stock at the time of the option exercise and the exercise price of that stock option. The aggregate intrinsic value of stock options exercised during the years ended December 31, 2021 and 2020 was $419,755 and $10,413. Stock-Based Compensation Expense The weighted-average assumptions used in the Black-Scholes option pricing model to determine the fair value of stock option grants were as follows: Years Ended December 31, 2021 2020 Risk-free interest rate 0.9 % 0.7 % Expected volatility 92.8 % 91.6 % Expected term (in years) 6.2 6.7 Expected dividend yield — % — % Expected volatility. The expected volatility assumption is based on volatilities of a peer group of similar companies whose share prices are publicly available. The peer group was developed based on companies in the life sciences industry. The Company will continue to apply this process until a sufficient amount of historical information regarding the volatility of its own stock price becomes available. Expected term. The expected term represents the period of time that options are expected to be outstanding. Because Private Oncternal did not have historical exercise behavior, it determined the expected term assumption using the simplified method for employees, which is an average of the contractual term of the option and its vesting period. The expected term for nonemployee options is generally the remaining contractual term . Risk-free interest rate. The risk-free interest rate is based on the implied yield on the U.S. Treasury securities with a maturity date similar to the expected term of the associated stock option award. Expected dividend yield. The Company bases the expected dividend yield assumption on the fact that it has never paid cash dividends and has no present intention to pay cash dividends and, therefore, used an expected dividend yield of zero. Stock-based compensation expense recognized for all equity awards has been reported in the statements of operations as follows (in thousands): Years Ended December 31, 2021 2020 Research and development $ 3,136 $ 544 General and administrative 2,739 1,012 $ 5,875 $ 1,556 At December 31, 2021, the total compensation cost related to nonvested awards not yet recognized was $17.4 million and the weighted-average period over which it is expected to be recognized was 3.2 years. Common Stock Reserved for Future Issuance Common stock reserved for future issuance is as follows (in thousands): December 31, 2021 2020 Common stock warrants 4,235 5,032 Common stock options issued and outstanding 6,445 2,226 Common stock available for issuance under equity plans 1,842 938 12,522 8,196 |