CHEBI:8116 - phorbol

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ChEBI Name phorbol
ChEBI ID CHEBI:8116
Definition A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(β), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5408557, eMolecules:516116, eMolecules:10178720, ZINC000019203136
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Formulae C20H28O6
C20H28O6
Net Charge 0
Average Mass 364.433
Monoisotopic Mass 364.18859
InChI InChI=1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1
InChIKey QGVLYPPODPLXMB-UBTYZVCOSA-N
SMILES C=1[C@@]2([C@@]([C@]3([C@@](C(=O)C(=C3)C)(CC1CO)O)[H])([C@H](C)[C@H]([C@@]4([C@]2(C4(C)C)[H])O)O)O)[H]
ChEBI Ontology
Outgoing phorbol (CHEBI:8116) has parent hydride tigliane (CHEBI:37526)
phorbol (CHEBI:8116) is a cyclic ketone (CHEBI:3992)
phorbol (CHEBI:8116) is a enone (CHEBI:51689)
phorbol (CHEBI:8116) is a tertiary α-hydroxy ketone (CHEBI:139592)
phorbol (CHEBI:8116) is a tertiary alcohol (CHEBI:26878)
phorbol (CHEBI:8116) is a tetracyclic diterpenoid (CHEBI:52557)
Incoming phorbol ester (CHEBI:37532) has functional parent phorbol (CHEBI:8116)
IUPAC Name
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one
Synonyms Sources
4,9,12β,13,20-pentahydroxy-1,6-tigliadien-3-on ChemIDplus
4,9,12β,13,20-pentahydroxytiglia-1,6-dien-3-one ChEBI
Phorbol KEGG COMPOUND
Manual Xrefs Databases
C00003465 KNApSAcK
C09155 KEGG COMPOUND
LMPR0104330001 LIPID MAPS
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Registry Numbers Types Sources
17673-25-5 CAS Registry Number ChemIDplus
2341335 Beilstein Registry Number Beilstein
Citation Type Source
27007853 PubMed citation Europe PMC
Last Modified
07 February 2018