Molecular Identity
Betulinic Acid
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
PubChem CID: 64971
Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an antineoplastic agent, an antimalarial, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane.
2D Structure
Properties
C30H48O3
Molecular Formula
456.70
Molecular Weight
g/mol
456.3603
Exact Mass
Da
8.2
XLogP
Above Lipinski threshold
57.5
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
3
H-Bond Acceptors
861
Complexity
SMILES
Canonical SMILES
SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)OIsomeric 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)C(=O)OSynonyms(20)
betulinic acid472-15-1MairinBetulic acidLupatic Acidals-3573-Hydroxylup-20(29)-en-28-oic acidbeta-betulinic acidNSC-113090NSC-6775783beta-Hydroxy-lup-20(29)-en-28-oic acid4G6A18707NCHEBI:3087DTXSID80861974(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Betulinic Acid
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