Lupeol
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Molecular Identity
Lupeol
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
PubChem CID: 259846
Lupeol is a pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. It has a role as an anti-inflammatory drug and a plant metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of a lupane.
2D Structure
Properties
C30H50O
Molecular Formula
426.70
Molecular Weight
g/mol
426.3862
Exact Mass
Da
9.9
XLogP
Above Lipinski threshold
20.2
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
1
H-Bond Acceptors
766
Complexity
SMILES
Canonical SMILES
SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CIsomeric SMILES
SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)CSynonyms(20)
Lupeol545-47-1FagarasterolClerodolMonogynol BFagarsterolLupenolTriterpene lupeolfarganasterolbeta-ViscolLup-20(29)-en-3-ol, (3-beta)-Lup-20(29)-en-3beta-olO268W13H3ONSC-90487(3-beta)-Lup-20(29)-en-3-ol
Data from PubChem (NCBI)
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