X0306 4 2014-09-22 0 0001404281 Tokai Pharmaceuticals Inc TKAI 0001404955 Harrison Seth Loring C/O TOKAI PHARMACEUTICALS, INC. ONE BROADWAY, 14TH FLOOR CAMBRIDGE MA 02142 1 0 1 0 Common Stock 2014-09-22 4 C 0 7549570 A 7549579 I See footnote. Common Stock 2014-09-22 4 P 0 362500 15.00 A 7912079 I See footnote. Common Stock 212694 D Series A Preferred Stock 2014-09-22 4 C 0 4500000 0.00 D Common Stock 429799 0 I See footnote. Series B-1 Preferred Stock 2014-09-22 4 C 0 798067 0.00 D Common Stock 76224 0 I See footnote. Series B-2 Preferred Stock 2014-09-22 4 C 0 644786 0.00 D Common Stock 61584 0 I See footnote. Series C Preferred Stock 2014-09-22 4 C 0 14604833 0.00 D Common Stock 1394921 0 I See footnote. Series D-1 Preferred Stock 2014-09-22 4 C 0 8711335 0.00 D Common Stock 832028 0 I See footnote. Series D-2 Preferred Stock 2014-09-22 4 C 0 1539643 0.00 D Common Stock 147053 0 I See footnote. Series D-3 Preferred Stock 2014-09-22 4 C 0 24046035 0.00 D Common Stock 2296661 0 I See footnote. Series E Preferred Stock 2014-09-22 4 C 0 24199308 0.00 D Common Stock 2311300 0 I See footnote. The Series A, Series B-1, Series B-2, Series C, Series D-1, Series D-2, Series D-3 and Series E Preferred Stock converted into Common Stock on a 10.47-for-one-basis upon the closing of the Issuer's initial public offering without payment of consideration. The Series A, Series B-1, Series B-2, Series C, Series D-1, Series D-2, Series D-3 and Series E Preferred Stock were convertible at any time at the holder's election and automatically upon the closing of the Issuer's initial public offering. The shares had no expiration date. Includes (a) 4,218,641 shares of Common Stock that are held by Apple Tree Partners II, L.P. and (b) 3,330,938 shares of Common Stock that are held by Apple Tree Partners II - Annex, L.P. The Reporting Person is a principal of the general partner of each of Apple Tree Partners II, L.P. and Apple Tree Partners II - Annex, L.P. and disclaims beneficial ownership of the shares held by each of Apple Tree Partners II, L.P. and Apple Tree Partners II - Annex, L.P., except to the extent of his pecuniary interest therein. The Reporting Person has sole voting and investment control and power over the shares held by Apple Tree Partners II, L.P. and Apple Tree Partners II - Annex, L.P. Includes (a) 237,500 shares of Common Stock acquired by Apple Tree Partners II - Annex, L.P. in the Issuer's initial public offering and (b) 125,000 shares of Common Stock acquired by Apple Tree Partners IV, L.P. in the Issuer's initial public offering. The Reporting Person is a principal of the general partner of each of Apple Tree Partners II - Annex, L.P. and Apple Tree Partners IV, L.P. and disclaims beneficial ownership of the shares held by each of Apple Tree Partners II - Annex, L.P. and Apple Tree Partners IV, L.P., except to the extent of his pecuniary interest therein. The Reporting Person has sole voting and investment control and power over the shares held by Apple Tree Partners II - Annex, L.P. and Apple Tree Partners IV, L.P. These shares were held by Apple Tree Partners II, L.P. The Reporting Person is a principal of the general partner of Apple Tree Partners II, L.P. and disclaims beneficial ownership of the shares held by Apple Tree Partners II, L.P., except to the extent of his pecuniary interest therein. The Reporting Person has sole voting and investment control and power over the shares held by Apple Tree Partners II, L.P. Includes (a) 13,370,422 shares of D-3 Preferred Stock that were held by Apple Tree Partners II, L.P. and (b) 10,675,613 shares of Series D-3 Preferred Stock that were held by Apple Tree Partners II - Annex, L.P. The Reporting Person is a principal of the general partner of each of Apple Tree Partners II, L.P. and Apple Tree Partners II - Annex, L.P. and disclaims beneficial ownership of the shares held by each of Apple Tree Partners II, L.P. and Apple Tree Partners II - Annex, L.P., except to the extent of his pecuniary interest therein. The Reporting Person has sole voting and investment control and power over the shares held by Apple Tree Partners II, L.P. and Apple Tree Partners II - Annex, L.P. These shares were held by Apple Tree Partners II - Annex, L.P. The Reporting Person is a principal of the general partner of Apple Tree Partners II - Annex, L.P. and disclaims beneficial ownership of the shares held by Apple Tree Partners II - Annex, L.P., except to the extent of his pecuniary interest therein. The Reporting Person has sole voting and investment control and power over the shares held by Apple Tree Partners II - Annex, L.P. /s/ Cindy Driscoll, Attorney-in-Fact 2014-09-24