(7) Convertible Preferred Stock

Prior to the closing of Company’s IPO, the Company’s convertible preferred stock was issuable in series. The number of authorized, issued, and outstanding shares of convertible preferred stock, the issuance date, net proceeds and the aggregate liquidation preferences for the convertible preferred stock as of January 31, 2017 and immediately prior to the automatic conversion of the convertible preferred stock into common stock were as follows (in thousands, except share data):

	Date issued	Number of shares authorized		Shares issued and outstanding		Liquidation preference
A	August 2008		1,533,329		1,533,329	$	4,600
B	July 2009		2,119,997		2,119,997		12,000
C	May 2011		1,312,311		1,312,311		18,100
D	July 2012		1,092,149		1,092,149		25,000
E	January 2014		1,681,912		1,641,662		71,377
E-1	January 2014		83,333		83,333		3,623
F	July 2015		2,828,185		2,828,185		124,554
Total outstanding as of January 31, 2017			10,651,216		10,610,966		259,254
F	February 2017		28,383		—		—
Total outstanding immediately prior to the closing of the Company’s IPO			10,679,599		10,610,966	$	259,254

In April 2017, the Company amended its Certificate of Incorporation to modify the automatic conversion terms that would apply to shares of Series E and E-1 Convertible Preferred Stock in the event that the Company completes a Qualified IPO in which the per share public offering price is less than the Series E and E-1 Convertible Preferred Stock purchase price of $43.47828 per share. In lieu of holders of the Series E and E-1 Convertible Preferred Stock having an election to receive cash in such circumstances, under the amended Certificate of Incorporation, the holders of Series E and E-1 Convertible Preferred Stock will have similar rights as the holders of Series F Convertible Preferred Stock if the per share public offering price in a Qualified IPO is less than 1.1x the Series E and E-1 Convertible Preferred purchase price, or $47.826108. As a result of this modification to Series E and E-1 Convertible Preferred Stock, the Company recorded a deemed dividend to Series E and E-1 Convertible Preferred Stock of $6.6 million resulting in a charge to accumulated deficit.

In June 2017, the Company amended its Certificate of Incorporation to eliminate certain variable rate adjustments to the conversion ratios of the Series E, E-1 and F Convertible Preferred Stock and replaced them with certain fixed conversion ratios for purposes of the IPO. Pursuant to these fixed conversion ratios, an additional 7,382,007 shares of common stock were issued to holders of Series E, E-1 and F Convertible Preferred Stock, as well as holders of shares of E-2 and F-2 Convertible Preferred Stock that were created in June 2017, who are referred to as the Series E-2 and F-2 Holders, upon the conversion of their shares immediately prior to the closing of the IPO. As an integral part of the foregoing transactions, the Company issued warrants to purchase up to 1,666,665 shares of common stock to the Series E-2 and F-2 Holders. The warrants are exercisable for ten years from the date of grant and have an exercise price of $16.44 per share, which represents 1.2x the fair value of the Company’s common stock as of the date of grant.

The issuance of additional shares of common stock upon conversion of the Series E, E-1, E-2, F, and F-2 Convertible Preferred Stock and the issuance of the common stock warrants are considered parts of a single, integrated transaction and was accounted for as an extinguishment of the originally issued Series E, E-1, and F Convertible Preferred Stock. The resulting gain on extinguishment was $26.3 million, which includes an amount of $14.6 million attributable to the warrants, and was recorded as a contribution of capital.

Immediately prior to the closing of the Company’s IPO, all shares of the Company’s then-outstanding convertible preferred stock, as shown in the table above, automatically converted into 17,992,973 shares of common stock in accordance with the terms of each series of preferred stock.

In addition, immediately prior to the closing of the Company’s IPO, all convertible preferred stock warrants automatically converted into common stock warrants. Accordingly, the Company revalued the convertible preferred stock warrants and reclassified the outstanding preferred stock warrant liability balance to additional paid-in capital with no further remeasurements as the common stock warrants are now deemed permanent equity. As a result of the automatic conversion, 68,633 shares of convertible preferred stock warrants converted into an aggregate 205,897 shares of common stock warrants. Of the 205,897 shares of common stock warrants, 34,058 shares will not be exercisable until such time that additional loan amount of $10.0 million under the New Facility Agreement is drawn.