Stockholders' Equity | 11. Stockholders’ Equity Preferred stock The Amended and Restated Certificate of Incorporation authorizes the Company to issue up to 15,000,000 shares of $ 0.001 par value preferred stock. Common stock The Amended and Restated Certificate of Incorporation authorizes the Company to issue up to 300,000,000 shares of $ 0.001 par value common stock. Private Placement On December 27, 2022, the Company entered into a Purchase Agreement and agreed to sell an aggregate of 7,331,377 shares of the Company’s common stock , as adjusted post-reverse share split,. On February 9, 2023, the Private Placement closed and the Company issued the shares. Common stock warrants As of September 30, 2023, the Company`s outstanding warrants to purchase shares of common stock consisted of the following: Issuance Date Number of Shares of Common Stock Issuable Exercise Price Classification Expiration Date May 9, 2017 1,696 $ $ 226.20 Equity May 8, 2027 July 19, 2019 2,192 $ $ 226.20 Equity July 18, 2029 3,888 Shares reserved for future issuance The Company has shares of common stock reserved for future issuances as follows: September 30, December 31, 2023 2022 Warrants to purchase common stock 3,888 3,888 Common stock options issued and outstanding 1,310,122 114,530 Common stock available for future grants 724,243 18,705 Restricted stock units issued and outstanding 24,782 62,353 Common stock available for ESPP 173,470 3 2008 Stock Plan and 2021 Equity Incentive Plan, as amended A summar y of stock option activity is set forth below (in thousands, except share and per share data): Number of Weighted Weighted Aggregate Outstanding, December 31, 2022 114,357 $ 166.72 8.0 $ 1 Options granted 1,271,964 $ 5.58 Options exercised ( 1,591 ) $ 6.53 Options forfeited or cancelled or expired ( 74,608 ) $ 48.96 Outstanding, September 30, 2023 1,310,122 $ 9.2 $ - Shares exercisable September 30, 2023 182,188 $ 79.83 7.9 $ - Vested and expected to vest, September 30, 2023 1,310,122 $ 17.18 9.2 $ - The aggregate intrinsic value is calculated as the difference between the exercise price of the underlying stock options and the fair value of the Company’s common stock for stock options that were in-the-money as of September 30, 2023 and December 31, 2022. The aggregate intrinsic value of stock options exercised during the three and nine months ended September 30, 2023 and 2022 was de minimis. The total fair value of options that vested during the nine months ended September 30, 2023 and 2022 was $ 2.6 million and $ 2.9 million, respectively. The options granted during the nine months ended September 30, 2023 and 2022 had a weighted-average per share grant-date fair value of $ 3.96 per share and $ 42.29 per share, respectively. As of September 30, 2023 , the total unrecognized stock-based compensation expense related to unvested stock options was $ 6.3 million, which is expected to be recognized over the remaining weighted-average vesting period of 3.1 years. Early exercise of stock options The terms of the 2008 Plan permit the exercise of certain options granted under the 2008 Stock Plan prior to vesting, subject to required approvals. The shares are subject to the Company’s lapsing repurchase right upon termination of employment at the original purchase price. The proceeds initially are recorded in accrued current liabilities from the early exercise of stock options and are reclassified to additional paid-in capital as the Company’s repurchase right lapses. During the three and nine months ended September 30, 2023 and 2022, the Company had no repurchases of common stock. As of September 30, 2023 and December 31, 2022, there were 4,761 shares and 9,401 shares that were subject to repurchase, respectively. The aggregate exercise prices of early exercised shares as of September 30, 2023 and December 31, 2022 were $ 0.1 million and $ 0.1 million, respectively, which were recorded in other current liabilities on the condensed balance sheets. Restricted Stock Units (RSU) A summary of RSU activity is set forth below: During third quarter 2023, no RSU were granted under 2021 Plan. As of September 30, 2023 , the total unrecognized stock-based compensation expense related to unvested RSU was $ 1.1 million, which is expected to be recognized over the remaining weighted-average vesting period of 2.5 years. Number of Weighted Average Grant Date Fair Value Unvested, December 31, 2022 62,340 $ 51.65 Released ( 31,212 ) $ 51.41 Forfeited or cancelled ( 6,346 ) $ 52.17 Unvested, September 30, 2023 24,782 $ 51.83 2021 Employee Stock Purchase Plan, as amended (ESPP) The fair value of the predicted share purchase rights granted under the ESPP upon the commencement of the offering period was estimated on the date of grant using the Black-Scholes option pricing model. For the offering period commenced December 1, 2022, the Company applied the following assumptions: (i) risk- free interest rate 4.61 %, (ii) dividend rate 0 %, (iii) expected terms 0.5 year and 1.0 year, and (iv) volatility 77.21 % and 76.29 %, for the two tranches, respectively. For the offering period commenced June 1, 2023, the Company applied the following assumptions: (i) risk- free interest rate 4.61 %, (ii) dividend rate 0 %, (iii) expected terms 0.5 year and 1.0 year, and (iv) volatility 77.21 % and 76.29 %, for the two tranches, res pectively. Compensation expe nse of less than $ 0.1 million wa s recorded into the condensed statement of operations for the three and nine months ended September 30, 2023. Compensation expe nse of $ 0.1 million and $ 0.2 million wa s recorded into the condensed statement of operations for the three and nine months ended September 30, 2022. As of September 30, 2023, the total unrecognized compensation cost related to the ESPP tranches was immaterial, which will be amortized for the two offerings over weighted-average period of 0.3 years. Stock-based compensation associated with awards to employees and non-employees Total stock-based compensation expense recognized was as follows (in thous ands): Three Months Ended September 30, Nine Months Ended September 30, 2023 2022 2023 2022 Cost of goods sold $ 27 $ 97 $ 109 $ 240 Sales and marketing 258 729 1,229 1,918 Research and development 5 4 21 33 General and administrative 543 1,147 1,846 2,985 Total $ 833 $ 1,977 $ 3,205 $ 5,176 The above stock-based compensation expense related to the following equity-based awards (in thousands): Three Months Ended September 30, Nine Months Ended September 30, 2023 2022 2023 2022 Stock options $ 674 $ 954 $ 2,459 $ 2,969 RSU 154 852 706 1,982 ESPP 5 171 40 225 Total $ 833 $ 1,977 $ 3,205 $ 5,176 The Company estimated the fair value of stock options using the Black-Scholes option-pricing model. The fair value of stock options is being amortized on a straight-line b asis over the requisite service period of the awards. The fair value of stock options was estimated using the following weighted-average assumptions: Three Months Ended September 30, Nine Months Ended September 30, 2023 2022 2023 2022 Expected dividends 0 % 0 % 0 % 0 % Expected volatility 78.10 % 72.2 % 77.4 %- 78.1 % 70.8 %- 72.2 % Risk-free interest rate 4.0 % 2.8 % 4.2 % 1.9 %- 3.0 % Expected term 6 years 6 years 6 years 6 years |