Methyl Betulinate
Basic information
- CAS
2259-06-5- Standard SMILES
C=C(C)[C@@H]1CC[C@]2(C(=O)OC)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12- InChIKey
XNZIMRUZBOZIBC-JVRMVBBZSA-N- Molecular formula
- C31H50O3
- Average molar mass
- 470.7 g/mol
- Monoisotopic mass
- 470.37599545
Overview
Betulinic acid methyl ester is a triterpenoid.
Names & identifiers
- Preferred name
- Methyl Betulinate
- IUPAC
- methyl (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-carboxylate
- English name
- Betulinic acid methyl ester
- Molecular formula
- C31H50O3
- Molecular weight
- 470.73
Names & synonyms
METHYL BETULINATE2259-06-5methyl (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-carboxylateLup-20(29)-en-28-oic acid, 3-hydroxy-, methyl ester, (3beta)-methyl (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-carboxylateRefChem:1089547218-857-6Betulinic acid methyl esterbetulinic acid methylesterCHEMBL295602MFCD00017379NSC152532
Show more names
Methylbetulinatebetulinate, MethylBETULINIC ACID METHYL ESTER hplcBETULINIC ACID METHYLESTER WITH HPLC3B-HYDROXY-LUP-20(29)-EN-28-OIC ACID METHYL ESTERLup-20(29)-en-28-oic acid, 3-hydroxy-, methyl ester, (3)-Lup-20(29)-en-28-oic acid, 3-hydroxy-, methyl ester, (3β)-
Properties
Computed structural properties
- XLogP
- 8.5
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 876
Physicochemical properties
- Melting point
- 222 · 222-223°C
- Boiling point
- 523.5 · 523.5±33.0 °C(Predicted)
- Density
- 1.036 · 1.036±0.06 g/cm3(Predicted)
- pka
- 15.16 · 15.16±0.70(Predicted)
- form
- A solid
- LogP
- 9.4 · 9.400 (est)
Chemistry & industry
Applications
DescriptionBetulinic acid methyl ester is a lupane-type triterpenoid and an esterified version of betulinic acid that has been found in Helicteres hirsuta and has diverse biological activities. It inhibits HIV-1 reverse transcriptase (IC50 = 11 μM). Betulinic acid methyl ester is active against L. braziliensis and T. cruzi (IC50s = 69.9 and 93.3 μM, respectively). It induces melanogenesis in (EC50 = 2.5 μM) and inhibits the growth of B16 2F2 melanoma cells in vitro (IC50 = 4.9 μM). Betulinic acid methyl ester is cytotoxic to SK-LU-1, HepG2, HeLa, SK-MEL-2, and AGS cells (IC50s = 60.84, 77.43, 80.17, 66.17, and 69.94 μg/ml, respectively).
UsesBetulinic acid methyl ester, a betulinic acid derivative, possesses antiprotozoal activity[1].
Additional notes
DefinitionChEBI: Betulinic acid methyl ester is a triterpenoid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…