Structure Database (LMSD)
Common Name
Phorbol
Systematic 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
- 4,9,12beta,13,20-pentahydroxy-1,6-tigliadien-3-on
- 4,9,12beta,13,20-pentahydroxytiglia-1,6-dien-3-one
- Phorbol
3D model of Phorbol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
Phorbol is a diterpene originally isolated from croton oil.1 It is used as a starting material for the semisynthesis of various phorbol diesters, which are structurally analogous to diacylglycerol and activate PKC isoforms by associating with their C1 domains.2
This information has been provided by Cayman Chemical
References
1. Hurley, J.H., Newton, A.C., Parker, P.J., et al. Taxonomy and function of C1 protein kinase C homology domains. Protein Sci. 6(2), 477-480 (1997).
2. Bohm, R., Flaschentrager, B., and Lendle, L. The activity of substances from croton oil. Archiv fuer Experimentelle Pathologie und Pharmakologie 177, 212-220 (1935).
String Representations
InChiKey (Click to copy)
QGVLYPPODPLXMB-UBTYZVCOSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@@]12([H])C([C@]1(O)[C@@H]([C@@H](C)[C@]1(O)[C@]3([H])C=C(C(=O)[C@]3(CC(CO)=C[C@@]21[H])O)C)O)(C)C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
4
Aromatic Rings
0
Rotatable Bonds
1
Van der Waals Molecular Volume
349.94
Topological Polar Surface Area
118.22
Hydrogen Bond Donors
5
Hydrogen Bond Acceptors
6
logP
1.36
Molar Refractivity
95.36
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