NCBI Taxonomy: 756026

Euphorbia epithymoides (ncbi_taxid: 756026)

found 22 associated metabolites at species taxonomy rank level.

Ancestor: Euphorbia sect. Helioscopia

Child Taxonomies: none taxonomy data.

Ingenol

1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR-(1A.ALPHA.,2.BETA.,5.BETA.,5A.BETA.,6.BETA.,8A.ALPHA.,9.ALPHA.,10A.ALPHA.))-

C20H28O5 (348.1936638)


Ingenol is a tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastereomer). It is a tetracyclic diterpenoid and a cyclic terpene ketone. Ingenol is a natural product found in Euphorbia villosa, Euphorbia illirica, and other organisms with data available. Ingenol is a PKC activator, with a Ki of 30 μM, with antitumor activity. Ingenol is a PKC activator, with a Ki of 30 μM, with antitumor activity.

   

4-(acetyloxy)-2,11-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

4-(acetyloxy)-2,11-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

C29H38O7 (498.2617398)


   

(1r,2r,3s,4s,5r,7r,9r,10r,11r,13s)-4-(acetyloxy)-2-hydroxy-10-methoxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadecan-7-yl benzoate

(1r,2r,3s,4s,5r,7r,9r,10r,11r,13s)-4-(acetyloxy)-2-hydroxy-10-methoxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadecan-7-yl benzoate

C30H40O7 (512.2773890000001)


   

4-(acetyloxy)-2-hydroxy-10-methoxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadecan-7-yl benzoate

4-(acetyloxy)-2-hydroxy-10-methoxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹¹,¹³]pentadecan-7-yl benzoate

C30H40O7 (512.2773890000001)


   

(1s,2s,3r,4r,5s,7s,9r,10s,11s,13r)-4-(acetyloxy)-2,11-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

(1s,2s,3r,4r,5s,7s,9r,10s,11s,13r)-4-(acetyloxy)-2,11-dihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

C29H38O7 (498.2617398)


   

(1s,2s,3r,4r,5s,7s,9r,10s,11s,13r)-4-(acetyloxy)-2-hydroxy-11-methoxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

(1s,2s,3r,4r,5s,7s,9r,10s,11s,13r)-4-(acetyloxy)-2-hydroxy-11-methoxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

C30H40O7 (512.2773890000001)


   

11,13-bis(acetyloxy)-3,6,6,14-tetramethyl-10-methylidene-2-oxotricyclo[10.3.0.0⁵,⁷]pentadec-3-en-1-yl acetate

11,13-bis(acetyloxy)-3,6,6,14-tetramethyl-10-methylidene-2-oxotricyclo[10.3.0.0⁵,⁷]pentadec-3-en-1-yl acetate

C26H36O7 (460.2460906)


   

(1r,3e,5r,7s,11r,12r,13s,14r)-11,13-bis(acetyloxy)-3,6,6,14-tetramethyl-10-methylidene-2-oxotricyclo[10.3.0.0⁵,⁷]pentadec-3-en-1-yl acetate

(1r,3e,5r,7s,11r,12r,13s,14r)-11,13-bis(acetyloxy)-3,6,6,14-tetramethyl-10-methylidene-2-oxotricyclo[10.3.0.0⁵,⁷]pentadec-3-en-1-yl acetate

C26H36O7 (460.2460906)


   

16-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl benzoate

16-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl benzoate

C29H36O6 (480.2511756)


   

(1r,2r,4r,7s,9r,10e,13r,15r,16s)-16-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl benzoate

(1r,2r,4r,7s,9r,10e,13r,15r,16s)-16-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl benzoate

C29H36O6 (480.2511756)


   

4-(acetyloxy)-2-hydroxy-11-methoxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

4-(acetyloxy)-2-hydroxy-11-methoxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

C30H40O7 (512.2773890000001)