Stockholders' Equity | 8. Stockholders’ Equity Common Stock At-The-Market Equity Offerings On September 28, 2017, the Company entered into an at-the-market sales agreement (the 2017 Sales Agreement) with Cowen and Company, LLC (Cowen) to sell up to $100.0 million of the Company’s common stock registered under a shelf registration statement filed with the U.S. Securities and Exchange Commission in September 2017. During the year ended December 31, 2020, the Company issued and sold 4,136,742 shares of common stock under the 2017 Sales Agreement at a weighted average price per share of $3.52, for aggregate net proceeds of $14.1 million, after deducting commissions and offering expenses. There were no shares sold under the 2017 Sales Agreement during the years ended December 31, 2018 or 2019. The shelf registration statement under which the shares that could be sold under the 2017 Sales Agreement were registered, expired on October 6, 2020. On October 7, 2020, the Company filed a prospectus supplement to a new shelf registration statement that it filed in May 2019 and entered into a new at-the-market sales agreement (the 2020 Sales Agreement) with Cowen. Under the 2020 Sales Agreement, the Company may sell up to $100.0 million of the Company’s common stock registered under the shelf registration statement that was filed in May 2019. The 2020 Sales Agreement replaces the 2017 Sales Agreement between the Company and Cowen, and the $100.0 million that may be sold under the 2020 Sales Agreement excludes any amounts that were sold under the 2017 Sales Agreement. During the year ended December 31, 2020, the Company issued and sold 1,024,760 shares of common stock under the 2020 Sales Agreement at a weighted average price per share of $3.74, for aggregate net proceeds of $3.7 million, after deducting commissions and offering expenses. Subsequent to December 31, 2020 and through February 26, 2021, the Company sold an additional 2,475,949 shares of common stock under the 2020 Sales Agreement at a weighted average price of $3.92, for aggregate net proceeds of $9.4 million, after deducting commissions and offering expenses. Public Offerings of Common Stock In March 2018, the Company completed a public offering in which the Company sold 8,050,000 shares of its common stock at a price to the public of $17.00 per share. The Company received net proceeds of $128.4 million from this offering, after deducting underwriting discounts, commissions and other offering expenses. Warrants to Acquire Company Stock In connection with the prior issuance of convertible unsecured promissory notes, the Company issued warrants to purchase shares of common stock. During the year ended December 31, 2018, all of the outstanding warrants for an aggregate of 553,868 shares were exercised at an exercise price of $0.33; a total of 536,564 shares of common stock were issued to stockholders upon the net exercise of 546,709 outstanding warrants, and 7,159 shares of common stock were issued to stockholders upon the cash exercise of outstanding warrants, for total proceeds to the Company of $2,336. The Company no longer has any outstanding warrants to purchase shares of its capital stock. 2003 Stock Incentive Plan The 2003 Stock Incentive Plan (the 2003 Plan) provided for the grant of incentives and nonqualified stock options and restricted stock awards. The exercise price for incentive stock options must be at least equal to the fair value of the common stock on the grant date. Unless otherwise stated in a stock option agreement, 25% of the shares subject to an option grant will vest upon the first anniversary of the vesting start date and thereafter at the rate of one forty A summary of the Company’s stock option activity under the 2003 Plan for the year ended December 31, 2020 is as follows: WEIGHTED- AGGREGATE WEIGHTED- AVERAGE INTRINSIC AVERAGE REMAINING VALUE OUTSTANDING EXERCISE CONTRACTUAL (IN OPTIONS PRICE TERM (YEARS) THOUSANDS) Outstanding as of December 31, 2019 382,337 $ 1.33 1.3 Options exercised (285,087) 1.12 Options forfeited — — Outstanding December 31, 2020 97,250 1.96 1.3 $ 175 During 2020, 2019 and 2018 the Company issued 285,087, 284,743 and 46,131 shares of common stock, respectively, in conjunction with exercises of stock options granted under the 2003 Plan. The Company received cash proceeds from the exercise of these stock options of $319,297, $318,912 and $59,659 during 2020, 2019 and 2018, respectively. Total intrinsic value of the options exercised during the years ended December 31, 2020, 2019 and 2018 was $921,168, $924,688 and $716,920, respectively. As of December 31, 2020, the options under the 2003 Plan were fully expensed and all options outstanding under the 2003 Plan were fully vested. There were no options granted under the 2003 Plan in 2020, 2019 or 2018. 2013 Equity Incentive Plan The Company’s board of directors adopted, and its stockholders approved, its 2013 Equity Incentive Plan (the 2013 Plan) effective on January 9, 2014. The 2013 Plan provides for the grant of incentive stock options within the meaning of Section 422 of the Internal Revenue Code (the Code), to the Company’s employees and its parent and subsidiary corporations’ employees, and for the grant of nonstatutory stock options, restricted stock awards, restricted stock unit awards, stock appreciation rights, performance stock awards and other forms of stock compensation to its employees, including officers, consultants and directors. The 2013 Plan also provides for the grant of performance cash awards to the Company’s employees, consultants and directors. Unless otherwise stated in a stock option agreement, 25% of the shares subject to an option grant will typically vest upon the first anniversary of the vesting start date and thereafter at the rate of one forty Authorized Shares The maximum number of shares of common stock that may be issued under the 2013 Plan was 1,000,000 shares, plus any shares subject to stock options or similar awards granted under the 2003 Plan that expire or terminate without having been exercised in full or are forfeited to or repurchased by the Company. The number of shares of common stock reserved for issuance under the 2013 Plan will automatically increase on January 1 of each year, beginning on January 1, 2015 and ending on January 1, 2023, by 3% of the total number of shares of common stock outstanding on December 31 of the preceding calendar year, or a lesser number of shares as may be determined by the Company’s board of directors. The maximum number of shares that may be issued pursuant to exercise of incentive stock options under the 2013 Plan is 20,000,000. Shares issued under the 2013 Plan may be authorized but unissued or reacquired shares of common stock. Shares subject to stock awards granted under the 2013 Plan that expire or terminate without being exercised in full, or that are paid out in cash rather than in shares, will not reduce the number of shares available for issuance under the 2013 Plan. Additionally, shares issued pursuant to stock awards under the 2013 Plan that the Company repurchases or that are forfeited, as well as shares reacquired by the Company as consideration for the exercise or purchase price of a stock award or to satisfy tax withholding obligations related to a stock award, will become available for future grant under the 2013 Plan. Stock Options A summary of the Company’s stock option activity under the 2013 Plan for the year ended December 31, 2020 is as follows: WEIGHTED- WEIGHTED- AVERAGE AGGREGATE AVERAGE REMAINING INTRINSIC OUTSTANDING EXERCISE CONTRACTUAL VALUE (IN OPTIONS PRICE TERM(YEARS) THOUSANDS) Outstanding as of December 31, 2019 4,399,606 $ 10.43 6.8 Options granted 1,473,100 4.49 Options exercised — — Options forfeited (119,495) 8.65 Outstanding as of December 31, 2020 5,753,211 8.93 6.6 $ 101 Vested or expected to vest as of December 31, 2020 5,753,211 8.93 6.6 $ 101 Exercisable as of December 31, 2020 3,588,799 9.87 5.3 $ — As of December 31, 2020, there was $9,417,298 of total unrecognized compensation expense related to unvested options that will be recognized over a weighted-average period of approximately 2.2 years. The total fair value of options that vested in the years ended December 31, 2020, 2019 and 2018 was $7,347,548, $6,159,610 and $3,003,632, respectively. During the years ended December 31, 2019 and 2018, the Company received cash of $94,001 and $962,530, respectively, and issued 16,606 and 144,182 shares of common stock, respectively, in conjunction with exercises of stock options granted under the 2013 Plan. The intrinsic value of the options exercised for the years ended December 31, 2019 and 2018 was $97,429 and $1,344,026, respectively. There were no shares exercised under the 2013 Plan in 2020. Restricted Stock Units (RSUs) A restricted stock unit (RSU) is a stock award that entitles the holder to receive shares of the Company’s common stock as the award vests. The fair value of each RSU is based on the closing price of the Company’s common stock on the date of grant. In September 2019, the Company granted an aggregate of 332,106 RSUs with service conditions to the Company’s non-executive employees. The RSUs granted in September 2019 vest over a two-year period, with one -third vesting on the first anniversary of the date of grant and the remaining two -thirds vesting on the second anniversary of the date of grant, provided that the employee remains employed with the Company at the applicable vesting date. As of December 31, 2020, there was $464,263 of total unrecognized compensation expense associated with these RSU grants that will be recognized over a weighted-average period of approximately 0.7 years. The following is a summary of RSU activity for the 2013 Plan for the year ended December 31, 2020: Weighted-Average Number of Shares Grant Date Underlying RSUs Fair Value Unvested at December 31, 2019 324,550 $ 4.53 Granted — — Forfeited (27,917) 4.53 Vested (104,100) 4.53 Unvested at December 31, 2020 192,533 4.53 Inducement Plan In January 2020, the Company’s board of directors adopted the GlycoMimetics, Inc. Inducement Plan (the Inducement Plan). The Inducement Plan provides for the grant of nonstatutory stock options, restricted stock awards, restricted stock unit awards, stock appreciation rights and other forms of stock awards to individuals not previously an employee or director of the Company as an inducement for such individuals to join the Company. Unless otherwise stated in an applicable stock option agreement, one A summary of the Company’s stock option activity under the Inducement Plan for the year ended December 31, 2020 is as follows: WEIGHTED- AGGREGATE WEIGHTED- AVERAGE INTRINSIC AVERAGE REMAINING VALUE OUTSTANDING EXERCISE CONTRACTUAL (IN OPTIONS PRICE TERM (YEARS) THOUSANDS) Outstanding as of December 31, 2019 — $ — — Options granted 100,600 3.09 Options exercised — — Options forfeited — — Outstanding as of December 31, 2020 100,600 3.09 9.5 $ 71 Vested or expected to vest as of December 31, 2020 100,600 3.09 9.5 $ 71 Exercisable as of December 31, 2020 — — — $ — As of December 31, 2020, there was $194,687 of total unrecognized compensation expense related to unvested options under the Inducement Plan that will be recognized over a weighted-average period of approximately 3.5 years. There were no options vested or exercised under the Inducement Plan during the year ended December 31, 2020. The weighted-average fair value of the options granted during the years ended December 31, 2020, 2019 and 2018 was $3.17, $7.17 and $12.90 per share, respectively, applying the Black-Scholes-Merton option pricing model utilizing the following weighted-average assumptions: 2020 2019 2018 Expected term 6.25 years 6.25 years 6.25 years Expected volatility 84.40% 71.15% 73.75% Risk-free interest rate 1.41% 2.54% 2.55% Expected dividend yield 0% 0% 0% Total stock-based compensation expense associated with stock options and RSUs was classified as follows on the statement of operations for the years ended December 31: 2020 2019 2018 Research and development expense $ 2,946,952 $ 2,402,242 $ 1,709,390 General and administrative expense 3,954,806 3,812,848 2,877,708 Total stock-based compensation expense $ 6,901,758 $ 6,215,090 $ 4,587,098 |