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Stockholders' Equity | 12 Months Ended
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Dec. 31, 2021
Stockholders' Equity |
Stockholders' Equity | 8. Stockholders’ Equity ​ Preferred Stock ​ Under the Company’s amended and restated certificate of incorporation, the Company has 5,000,000 shares of preferred stock authorized for issuance, with a $0.001 par value per share. Preferred stock may be issued from time to time in one or more series, each series to have such terms as stated or expressed in the resolutions providing for the issue of such series adopted by the board of directors of the Company. Preferred stock which may be redeemed, purchased or acquired by the Company may be reissued except as otherwise provided by law. As of December 31, 2021, the Company had 31,455 shares of Series X Preferred Stock outstanding. Each share of Series X Preferred Stock is convertible into 166.67 shares of common stock and therefore the number of shares of underlying common stock issuable upon conversion of the Series X Preferred Stock is 5,242,501. Refer to Note 1 – “Organization and Operations” regarding the Company’s issuance of Series X Preferred Stock in January 2021 and February 2021. ​ Outstanding Warrants The following table presents information about warrants that are issued and outstanding at December 31, 2021: ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
Year Issued |  | Equity Instrument |  | Warrants Outstanding |  | Exercise Price |  | Date of Expiration
2015 |  | Common Stock |  | 204 | ​ | $ | 732.72 |  | 3/30/2022
2018 |  | Common Stock |  | 699,962 | ​ | $ | 72.00 |  | 6/21/2023
2019 |  | Common Stock |  | 331,858 | ​ | $ | 37.50 |  | 2/7/2024
2021 |  | Common Stock |  | 498,356 | ​ | $ | 2.10 |  | 12/14/2030
Total |  |  |  | 1,530,380 | ​ |  |  |  |
Weighted average exercise price |  |  |  |  | ​ | $ | 41.84 |  |
Weighted average life in years |  |  |  |  | ​ |  |  |  | 4.05
​ Common Stock ​ As of December 31, 2021, the Company had 150,000,000 shares of common stock authorized for issuance, $0.001 par value per share, with 13,016,955 shares issued and outstanding. The voting, dividend and liquidation rights of holders of common stock are subject to and qualified by the rights, powers and preferences of the holders of any outstanding preferred stock. ​ Reserved for Future Issuance ​ The Company has reserved for future issuance the following shares of common stock: ​
​ | ​ | ​ | ​ | ​
​ | ​ | December 31, | ​ | December 31,
​ |  | 2021 |  | 2020
Series X Preferred Stock |  | 5,242,501 |  | —
Warrants for the purchase of common stock |  | 1,530,380 |  | 1,032,291
Options outstanding to purchase common stock |  | 1,346,733 |  | 227,846
Options available for future issuance to purchase common stock | ​ | 1,633,736 | ​ | 322,695
Shares reserved for the employee stock purchase plan | ​ | 30,904 | ​ | 24,825
Total |  | 9,784,254 |  | 1,607,657
​ As of December 31, 2021, the Company also had 31,455 shares of Series X Preferred Stock outstanding. Each share of Series X Preferred Stock outstanding is convertible into 166.67 shares of the Company’s common stock, subject to certain beneficial ownership limitations at the holder’s option. See Note 1 – “Organization and Operations” for additional detail.

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- Definition The entire disclosure for terms, amounts, nature of changes, rights and privileges, dividends, and other matters related to preferred stock. + References Reference 1: http://fasb.org/us-gaap/role/ref/legacyRef -Publisher FASB -Name Accounting Standards Codification -Topic 505 -URI http://asc.fasb.org/topic&trid=2208762 + Details
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