In connection with certain of its redeemable convertible preferred stock issuances, debt agreements, convertible debt and other financing arrangements, the Company has issued warrants for shares of its common stock and various issues of its redeemable convertible preferred stock which have since been converted to common stock warrants.

In connection with the March 2022 Securities Purchase Agreement (see Note 14), the Company issued and sold pre-funded warrants exercisable for an aggregate of 200,911 shares of common stock. The pre-funded warrants had an exercise price of $0.012 per share and were exercised in full in May 2022 for proceeds of $2,411. The Company also issued and sold to the investor common warrants to purchase 270,415 shares of common stock that will expire on March 17, 2024 and common warrants to purchase an additional 270,415 shares of common stock that will expire on September 17, 2027. Each of these common warrants became exercisable commencing September 21, 2022 and has an exercise price of $24.744 per share.

In connection with the December 2022 Securities Purchase Agreement (see Note 14), the Company issued and sold pre-funded warrants exercisable for an aggregate of 1,188,322 shares of common stock. The pre-funded warrants had an exercise price of $0.001 per share and were exercised in full in December 2022 for proceeds of $1,188. The Company also issued and sold to the investor warrants to purchase 1,290,322 shares of common stock that will expire on December 23, 2027 and warrants to purchase an additional 1,290,322 shares of common stock that will expire on December 23, 2024. Each of these common warrants became exercisable commencing December 23, 2022 and has an exercise price of $7.50 per share.

Also in connection with the December 2022 Securities Purchase Agreement, the Company issued warrants to purchase up to an aggregate of 38,709 shares of common stock to designees of the placement agent for the transaction. The warrants issued to the placement agent have substantially the same terms as the warrants above, except the placement agent warrants have an exercise price of $9.6875 per share and expire on December 21, 2027.

The following table shows the common stock warrants outstanding as of December 31, 2022:


Warrant Issuance Date	Shares of Common Stock Underlying Warrants		Exercise Price/Share		Expiration Date
August 2014		159	$	4,231.80	2024
March 2016		251		496.80	2026
March 2018		100		1,391.40	2028
June 2020		3,574		139.878	2030
March 2022		270,415		24.74	2024
March 2022		270,415		24.74	2027
December 2022		1,290,322		7.50	2024
December 2022		1,290,322		7.50	2027
December 2022		38,709		9.6875	2027