Convertible Preferred Stock and Stockholders’ Equity | 8 . Convertible Preferred Stock and Stockholders’ Equity Convertible Preferred Stock In November 2016, the Company completed a private placement of stock in which investors, certain of which are affiliated with the directors and officers of the Company, purchased convertible preferred stock and common stock of the Company (the November 2016 Placement). The Company issued 2,819,549 shares of non-voting Class A Convertible Preferred Stock (the Class A Preferred) at $13.30 per share, each of which is convertible into five shares of common stock upon certain conditions defined in the Certificate of Designation of Preferences, Rights and Limitations of the Class A Preferred filed with the Delaware Secretary of State on November 22, 2016 (the CoD). The Class A Preferred were purchased exclusively by entities affiliated with Redmile Group, LLC (collectively, Redmile). The terms of the CoD prohibited Redmile from converting the Class A Preferred into shares of the Company’s common stock if, as a result of conversion, Redmile, together with its affiliates, would own more than 9.99% of the Company’s common stock then issued and outstanding (the Redmile Percentage Limitation), which percentage could change at Redmile’s election upon 61 days’ notice to the Company to (i) any other number less than or equal to 19.99% or (ii) subject to approval of the Company’s stockholders to the extent required in accordance with the Nasdaq Global Market rules, any number in excess of 19.99%. On May 2, 2017, the Company’s stockholders approved the issuance of up to an aggregate of 14,097,745 shares of common stock upon the conversion of the outstanding shares of Class A Preferred. As a result, Redmile has the right to increase the Redmile Percentage Limitation to any percentage in excess of 19.99% at its election. The Company also issued 7,236,837 shares of common stock at $2.66 per share as part of the November 2016 Placement. Gross proceeds from the November 2016 Placement were $56.7 million, and after giving effect to costs related to placement, net proceeds were $54.9 million. The Class A Preferred are non-voting shares and have a stated par value of $0.001 per share and are convertible into five shares of the Company’s common stock at a conversion price of $2.66 per share, which was the fair value of the Company’s common stock on the date of issuance. Holders of the Class A Preferred have the same dividend rights as holders of the Company’s common stock. Additionally, the liquidation preferences of the Class A Preferred are pari passu The Company evaluated the Class A Preferred for liability or equity classification under ASC 480, Distinguishing Liabilities from Equity, The Company also evaluated the Class A Preferred in accordance with the provisions of ASC 815, Derivatives and Hedging, The issuance of convertible preferred stock could generate a beneficial conversion feature (BCF), which arises when a debt or equity security is issued with an embedded conversion option that is beneficial to the investor (or in-the-money) at inception because the conversion option has an effective strike price that is less than the market price of the underlying stock on the commitment date. The Class A Preferred have an effective conversion price of $2.66 per common share, which was equal to the market price of the Company’s stock on the commitment date. Therefore, no BCF was present. The Company also entered into a registration rights agreement (the Registration Rights Agreement) with certain of the purchasers in the November 2016 Placement, excluding those purchasers affiliated with the Company’s directors and officers, requiring the Company to register for the resale of the relevant shares. The Company registered all of the relevant shares issued in the November 2016 Placement for resale on a Form S-3 filed with the SEC, as required under the Registration Rights Agreement, and the registration statement was declared effective in January 2017. Stock Options and Restricted Stock Units Stock option activity under all equity and stock option plans is summarized as follows: Number of Options Weighted- Average Price Balance at December 31, 2018 6,980,581 $ 5.58 Granted 3,131,360 16.46 Cancelled (270,172 ) 10.39 Exercised (614,965 ) 3.18 Balance at June 30, 2019 9,226,804 $ 9.29 Restricted stock unit activity under all equity and stock option plans is summarized as follows: Number of Restricted Stock Units Weighted- Average Grant Date Fair Value per Share Balance at December 31, 2018 188,625 $ 4.89 Granted 520,000 16.41 Cancelled (16,000 ) 4.89 Vested — — Balance at June 30, 2019 692,625 $ 13.54 The allocation of stock-based compensation for all stock awards is as follows (in thousands): Three Months Ended June 30, Six Months Ended June 30, 2019 2018 2019 2018 Research and development $ 2,479 $ 853 $ 4,662 $ 1,659 General and administrative 1,907 632 3,592 1,208 Total $ 4,386 $ 1,485 $ 8,254 $ 2,867 As of June 30, 2019, the unrecognized compensation cost related to outstanding options was $43.3 million and is expected to be recognized as expense over a weighted average period of approximately 3.2 years. As of June 30, 2019, the unrecognized compensation cost related to restricted stock units was $7.5 million which is expected to be recognized as expense over a weighted average period of approximately 3.1 years. As of January 1, 2019, the Company adopted ASU 2018-07, which aligned the guidance on share-based payments to nonemployees with that for share-based payments to employees. As such, the measurement of equity-classified nonemployee awards will be fixed at the grant date and entities are not required to remeasure nonemployee equity awards at each reporting date until such time that the measurement date is established. The weighted-average assumptions used in the Black-Scholes option pricing model to determine the fair value of the employee and nonemployee stock option grants were as follows: Six Months Ended June 30, 2019 2018 Risk-free interest rate 2.5 % 2.4 % Expected volatility 79.8 % 79.0 % Expected term (in years) 6.1 6.1 Expected dividend yield 0.0 % 0.0 % Reconciliation of Consolidated Stockholders’ Equity Accounts The following table summarizes the Company’s changes in stockholders’ equity accounts for the three and six months ended June 30, 2019 (in thousands, except share data): Convertible Preferred Stock Common Stock Additional Paid-in Accumulated Other Comprehensive Accumulated Total Stockholders' Shares Amount Shares Amount Capital Loss Deficit Equity Balance at December 31, 2018 2,819,549 $ 3 64,693,681 $ 65 $ 445,799 $ (2 ) $ (285,396 ) $ 160,469 Exercise of stock options, net of issuance costs — — 420,920 — 1,258 — — 1,258 Issuance of common stock upon cashless warrant exercise — — 1,245 — — — — — Stock-based compensation — — — — 3,868 — — 3,868 Unrealized gain on short-term investments — — — — — 2 — 2 Net loss — — — — — — (19,760 ) (19,760 ) Balance at March 31, 2019 2,819,549 $ 3 65,115,846 $ 65 $ 450,925 $ — $ (305,156 ) $ 145,837 Exercise of stock options, net of issuance costs — — 194,045 — 688 — — 688 Stock-based compensation — — — — 4,386 — — 4,386 Unrealized gain on short-term investments — — — — — 93 — 93 Net loss — — — — — — (23,478 ) (23,478 ) Balance at June 30, 2019 2,819,549 $ 3 65,309,891 $ 65 $ 455,999 $ 93 $ (328,634 ) $ 127,526 The following table summarizes the Company’s changes in stockholders’ equity accounts for the three and six months ended June 30, 2018 (in thousands, except share data): Convertible Preferred Stock Common Stock Additional Paid-in Accumulated Other Comprehensive Accumulated Total Stockholders' Shares Amount Shares Amount Capital Loss Deficit Equity Balance at December 31, 2017 2,819,549 $ 3 52,648,601 $ 53 $ 295,934 $ (3 ) $ (218,798 ) $ 77,189 Exercise of stock options, net of issuance costs — — 174,984 — 606 — — 606 Issuance of common stock upon cashless warrant exercise — — 34,149 — — — — — Stock-based compensation — — — — 1,382 — — 1,382 Issuance costs from public offering of common stock — — — — (37 ) — — (37 ) Unrealized loss on short-term investments — — — — — (10 ) — (10 ) Net loss — — — — — — (14,135 ) (14,135 ) Balance at March 31, 2018 2,819,549 $ 3 52,857,734 $ 53 $ 297,885 $ (13 ) $ (232,933 ) $ 64,995 Exercise of stock options, net of issuance costs — — 30,686 — 175 — — 175 Stock-based compensation — — — — 1,485 — — 1,485 Issuance costs from public offering of common stock — — — — (19 ) — — (19 ) Issuance of common stock for license agreements — — 500,000 — 4,845 — — 4,845 Unrealized loss on short-term investments — — — — — (2 ) — (2 ) Net loss — — — — — — (19,654 ) (19,654 ) Balance at June 30, 2018 2,819,549 $ 3 53,388,420 $ 53 $ 304,371 $ (15 ) $ (252,587 ) $ 51,825 |