Classification Term: 170291
Indole-Diterpenoid alkaloids (Penitrems) (ontology term: 70f597084419afb7654cf172d0e42047)
found 52 associated metabolites at sub_class
metabolite taxonomy ontology rank level.
Ancestor: Tryptophan alkaloids
Child Taxonomies: There is no child term of current ontology term.
penitrem A
C37H44ClNO6 (633.2856993999999)
D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE Reference Standard (Level 1) Penitrem A is an indole diterpene neurotoxic alkaloid produced by Penicillium, acts as a selective BK channel antagonist with antiproliferative and anti-invasive activities against multiple malignancies. Penitrem A increases the spontaneous release of endogenous glutamate, gamma-aminobutyric acid (GABA) and aspartate from cerebrocortical synaptosomes, and induces tremorgenic syndromes in animals[1][2].
penitrem A
C37H44ClNO6 (633.2856993999999)
D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins Penitrem A is an indole diterpene neurotoxic alkaloid produced by Penicillium, acts as a selective BK channel antagonist with antiproliferative and anti-invasive activities against multiple malignancies. Penitrem A increases the spontaneous release of endogenous glutamate, gamma-aminobutyric acid (GABA) and aspartate from cerebrocortical synaptosomes, and induces tremorgenic syndromes in animals[1][2].
(1s,12r,14r,15r,16s,17s,20s)-14-hydroxy-1,16,20-trimethyl-16-(4-methylpent-3-en-1-yl)-3-azapentacyclo[10.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]icosa-2(10),4,6,8-tetraen-17-yl acetate
16-(4-hydroxy-4-methylpent-2-en-1-yl)-1,16,20-trimethyl-3-azapentacyclo[10.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]icosa-2(10),4,6,8-tetraen-17-ol
(1s,2s,5s,7s,10r,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraene-10-carbaldehyde
C28H37NO3 (435.27732920000005)
(1'r,2s,2'r,8'r,9s,9as,10's,11'r,12's,16's)-2,2',7',7',11',16'-hexamethyl-3,5'-dioxo-2,9a-dihydro-1h-6',15'-dioxaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadecan]-3'-en-10'-yl acetate
(2s)-1-[(1r,2s,13s,16s,17s,19r,20r,22s,25s,27s)-16-hydroxy-1,2,24,24-tetramethyl-22-(2-methylprop-1-en-1-yl)-18,21,23,26-tetraoxa-4-azaoctacyclo[14.13.0.0²,¹³.0³,¹¹.0⁵,¹⁰.0¹⁷,¹⁹.0¹⁷,²⁷.0²⁰,²⁵]nonacosa-3(11),5,7,9-tetraen-7-yl]-3-methylbutane-2,3-diol
7-(2-hydroxypropan-2-yl)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-9-ol
C28H39NO3 (437.29297840000004)
(1s,2r,5s,7s,8r,9r,11s,12s,15s)-19-[(2s)-3-chloro-2-hydroxy-3-methylbutyl]-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol
C32H44ClNO6 (573.2856994000001)
(1s,3s,7s,9r,10s,11r,16s,17s,26r,28s,29r)-22-chloro-16,17,34,34-tetramethyl-25-methylidene-11-(prop-1-en-2-yl)-2,8,12,33-tetraoxa-19-azadecacyclo[26.4.2.0³,¹⁷.0⁶,¹⁶.0⁷,⁹.0⁷,¹³.0¹⁸,³².0²⁰,³¹.0²³,³⁰.0²⁶,²⁹]tetratriaconta-18(32),20,22,30-tetraene-3,10,29-triol
C37H44ClNO7 (649.2806143999999)
19-(2-hydroxy-3-methoxy-3-methylbutyl)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraene-8,12-diol
2,2',7',7',11',16'-hexamethyl-3,5'-dioxo-2,9a-dihydro-1h-6',15'-dioxaspiro[imidazo[1,2-a]indole-9,14'-tetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadecan]-3'-en-10'-yl acetate
(1s,12s,15s,20r)-15-hydroxy-1,16,16,20-tetramethyl-3-azapentacyclo[10.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]icosa-2(10),4,6,8-tetraen-17-one
4,5,24,24-tetramethyl-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,18,20-hexaen-22-one
3-[(3s,4s,7s,9s,11s,12r,15s,26r,27s,31r)-7,27-dihydroxy-3,4,11,23,23,25,25-heptamethyl-31-(prop-1-en-2-yl)-8,24-dioxa-1-azanonacyclo[16.13.1.0²,¹⁷.0³,¹⁵.0⁴,¹².0⁷,¹¹.0²⁰,²⁸.0²¹,²⁶.0²⁹,³²]dotriaconta-2(17),18,20(28),21,29(32)-pentaen-9-yl]-3-hydroxy-2-methylpropanoic acid
12-hydroxy-8-(2-hydroxypropan-2-yl)-6-methoxy-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),22(27),29-hexaen-9-one
(1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol
(1s,2r,5s,6s,8r,9s,10r,12s,15r,16s,25r,27s,28r)-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol
(1s,2s,5s,7s,8r,9r,10s,11r,14s)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraene-8,9,10-triol
C27H37NO5 (455.26715920000004)
(1r,2s,5s,8r,9r,11s,14r,15s,24s,26r,27s)-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-2,5,8-triol
21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19,21,29-tetraene-5,9-diol
C37H44ClNO5 (617.2907843999999)
3-{[5-(3,4-dihydroxy-4-methylpentyl)-6-hydroxy-5,8a-dimethyl-1-methylidene-hexahydro-2h-naphthalen-2-yl]methyl}-1-(2-methylbut-3-en-2-yl)-3h-indol-2-one
(1s,4r,5s,23s,26s,30r)-26-hydroxy-4,5,13,13,15,15,31,31-octamethyl-14,32,33-trioxa-7-azanonacyclo[28.2.1.0¹,²⁷.0⁴,²⁶.0⁵,²³.0⁶,²¹.0⁸,²⁰.0¹⁰,¹⁸.0¹¹,¹⁶]tritriaconta-6(21),8,10(18),11(16),19,27-hexaene-17,29-dione
2,3,23,23,25,25-hexamethyl-8-(prop-1-en-2-yl)-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),10,18,20(28),21,26,29-heptaene-9,12-diol
(2r,3s,4s,5s,6r)-2-(hydroxymethyl)-6-{[(1s,12s,15r,16s,17s,20s)-1,16,20-trimethyl-16-(4-methylpent-3-en-1-yl)-3-azapentacyclo[10.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]icosa-2(10),4,6,8-tetraen-17-yl]oxy}oxane-3,4,5-triol
19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl 2-(acetyloxy)-2-methylpropanoate
(1s,2r,5s,7r,8r,11s,14s)-1,2-dimethyl-18-(3-methylbut-2-en-1-yl)-7-(prop-1-en-2-yl)-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaene-8,11-diol
1-{16-hydroxy-1,13,17,17-tetramethyl-9-azapentacyclo[10.8.0.0²,¹⁰.0³,⁸.0¹³,¹⁸]icosa-3,5,7-trien-9-yl}ethanone
8,11,24-trihydroxy-18-[2-(2-hydroxypropan-2-yl)-4-(prop-1-en-2-yl)cyclobutyl]-1,2-dimethyl-7-(prop-1-en-2-yl)-23-azapentacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁷,²²]tetracosa-9,17(22),18,20,23-pentaen-16-one
(1s,12s,15r,16s,17s,20s)-1,16,20-trimethyl-16-(4-methylpent-3-en-1-yl)-3-azapentacyclo[10.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]icosa-2(10),4,6,8-tetraen-17-yl acetate
C30H41NO2 (447.31371260000003)
(1s,2r,5s,7r,11s,14s)-5,11-dihydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one
C27H33NO5 (451.23586080000007)
(1s,2r,5s,7s,8r,9r,11s,16r)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10,13-trioxa-25-azaoctacyclo[14.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹²,¹⁴.0¹⁸,²⁶.0¹⁹,²⁴]hexacosa-18(26),19,21,23-tetraen-8-ol
C27H33NO5 (451.23586080000007)
(2e,4e)-5-[(10r,11s,17s,18s,21s,22s,23r,26s)-11,21-dihydroxy-7,7,9,9,17,18,22-heptamethyl-13-(3-methylbut-2-en-1-yl)-8-oxa-15-azaheptacyclo[14.11.0.0²,¹⁴.0⁴,¹².0⁵,¹⁰.0¹⁷,²⁶.0¹⁸,²³]heptacosa-1(16),2,4(12),5,13-pentaen-22-yl]-2-methylpenta-2,4-dienoic acid
2-[(1'r,2r,5r,12'r,15'r,20's)-5,15'-dihydroxy-1',20'-dimethyl-4,17'-dioxo-3'-azaspiro[oxolane-2,16'-pentacyclo[10.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]icosane]-2'(10'),4',6',8'-tetraen-5-yl]propan-2-yl acetate
C29H35NO7 (509.24134000000004)
5-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,11,16(24),17,19,21-hexaen-8-one
C27H31NO4 (433.22529660000004)
(1s,2s,4ar,5s,8ar)-5-(1h-indol-3-ylmethyl)-1,4a-dimethyl-6-methylidene-1-(4-methylpent-3-en-1-yl)-hexahydro-2h-naphthalen-2-ol
6-{[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-1,16,16,20-tetramethyl-3-azapentacyclo[10.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]icosa-2(10),4,6,8,18-pentaen-17-one
(1s,9r,13s,19s,22s,23s,25r,26r,28s,31s,33s,36r)-22-hydroxy-1,10,10,12,12,30,30,36-octamethyl-28-(2-methylprop-1-en-1-yl)-11,24,27,29,32-pentaoxa-3-azadecacyclo[17.17.0.0²,¹⁷.0⁴,¹⁶.0⁷,¹⁵.0⁹,¹³.0²²,³⁶.0²³,²⁵.0²³,³³.0²⁶,³¹]hexatriaconta-2(17),4,6,15-tetraen-8-one
(2e,4e)-5-[(3s,4s,7s,8s,9r,12s,23r,24s,28r)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-28-(prop-1-en-2-yl)-21-oxa-1-azaoctacyclo[13.13.1.0²,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²⁵.0¹⁸,²³.0²⁶,²⁹]nonacosa-2(14),15,17(25),18,26(29)-pentaen-8-yl]-2-methylpenta-2,4-dienoic acid
(2s,3r,8r,12s,15s,21s,22r)-12,21-dihydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁷]hentriaconta-1(17),5,10,18,20(28),26,29-heptaen-9-one
(3s)-3-{[(2s,4ar,5s,6s,8as)-5-[(3s)-3,4-dihydroxy-4-methylpentyl]-6-hydroxy-5,8a-dimethyl-1-methylidene-hexahydro-2h-naphthalen-2-yl]methyl}-1-(2-methylbut-3-en-2-yl)-3h-indol-2-one
8-(2-{6-amino-1,1,3,3-tetramethyl-4h,9h-indeno[2,1-c]pyran-7-yl}-2-oxoethyl)-10a-hydroxy-3-(2-hydroxypropan-2-yl)-6a,7-dimethyl-2-oxo-3h,4ah,5h,6h,8h,9h,10h-naphtho[2,1-b]pyran-7-carboxylic acid
(3r,4as,6ar,7s,8s,10as)-8-(2-{6-amino-1,1,3,3-tetramethyl-4h,9h-indeno[2,1-c]pyran-7-yl}-2-oxoethyl)-10a-hydroxy-3-(2-hydroxypropan-2-yl)-6a,7-dimethyl-2-oxo-3h,4ah,5h,6h,8h,9h,10h-naphtho[2,1-b]pyran-7-carboxylic acid
1-[22-(3,3-dimethyloxiran-2-yl)-16-hydroxy-1,2,24,24-tetramethyl-18,21,23,26-tetraoxa-4-azaoctacyclo[14.13.0.0²,¹³.0³,¹¹.0⁵,¹⁰.0¹⁷,¹⁹.0¹⁷,²⁷.0²⁰,²⁵]nonacosa-3(11),5,7,9-tetraen-9-yl]-3-methylbutane-2,3-diol
(1s,3s,7s,9r,10s,11r,16s,17s,26r,28s,29r)-3-methoxy-16,17,34,34-tetramethyl-25-methylidene-11-(prop-1-en-2-yl)-2,8,12,33-tetraoxa-19-azadecacyclo[26.4.2.0³,¹⁷.0⁶,¹⁶.0⁷,⁹.0⁷,¹³.0¹⁸,³².0²⁰,³¹.0²³,³⁰.0²⁶,²⁹]tetratriaconta-18(32),20,22,30-tetraene-10,29-diol
(1s,19s,22s,26r,31r)-2,22-dihydroxy-26-(2-hydroxypropan-2-yl)-1,9,9,11,11,31-hexamethyl-10,27-dioxa-3-azaheptacyclo[17.12.0.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹².0²²,³¹.0²³,²⁸]hentriaconta-2,4(16),5,7(12),14,23-hexaene-17,25-dione
1,2-dimethyl-7-{2-[(3-methylbut-2-en-1-yl)oxy]propan-2-yl}-6,10-dioxa-24-azaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁷,²⁵.0¹⁸,²³]pentacosa-17(25),18,20,22-tetraen-8-ol
C32H43NO4 (505.31919180000006)
(1s,2r,5s,10s,13s)-10-hydroxy-1,2-dimethyl-6-oxa-22-azahexacyclo[11.10.0.0²,¹⁰.0⁵,⁹.0¹⁵,²³.0¹⁶,²¹]tricosa-8,15(23),16,18,20-pentaen-7-one
C23H25NO3 (363.18343400000003)
7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-ol
C27H35NO3 (421.26168000000007)
(1s,2r,5s,6r,8r,9s,10r,12s,15r,16s,24r,25s,27s,28s)-5,9-dihydroxy-15,16,24,33,33-pentamethyl-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0²,¹⁶.0⁵,¹⁵.0⁶,⁸.0⁶,¹².0¹⁷,³¹.0¹⁹,³⁰.0²²,²⁹.0²⁵,²⁸]tritriaconta-17(31),19,21,29-tetraen-23-one
(1s,2r,5s,7r,8s,9r,12s,15s)-8,12,25-trihydroxy-1,2-dimethyl-21-(2-methylbut-3-en-2-yl)-7-(prop-1-en-2-yl)-6,10-dioxa-24-azahexacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁹,¹¹.0¹⁸,²³]pentacosa-18,20,22,24-tetraen-17-one
(1s,4r,5s,16s,19s,23r)-19-hydroxy-4,5,24,24-tetramethyl-11-(3-methylbut-2-en-1-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one
C32H39NO4 (501.28789340000003)