Fasciculic acid B
Basic information
- CAS
126882-55-1- Standard SMILES
C[C@H](CC[C@@H](O)C(C)(C)O)[C@H]1CC[C@@]2(C)C3=C(C[C@H](O)[C@]12C)[C@@]1(C)C[C@@H](OC(=O)CC(C)(O)CC(=O)O)[C@H](O)C(C)(C)C1CC3- InChIKey
SWRXIGFQDQTNKP-RAOJVCEKSA-N- Molecular formula
- C36H60O9
- Average molar mass
- 636.9 g/mol
- Monoisotopic mass
- 636.42373349
Overview
Fasciculic acid B is a triterpenoid.
Names & identifiers
- Preferred name
- Fasciculic acid B
- IUPAC
- 5-[[(2R,3R,10S,12S,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-3,12-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
- English name
- fasciculic acid B
- Molecular formula
- C36H60O9
- Molecular weight
- 636.87
Names & synonyms
Fasciculic acid B2-O-(3-Hydroxy-3-methylglutaryl) fasciculol BRefChem:1399885-[[(2R,3R,10S,12S,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-3,12-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-hydroxy-3-methyl-5-oxopentanoic acid126882-55-1SCHEMBL29934735CHEBI:168291Lanost-8-ene-2,3,12,24,25-pentol, 2-(hydrogen 3-hydroxy-3-methylpentanedioate), (2alpha,3beta,12alpha,24R)-Lanost-8-ene-2,3,12,24,25-pentol, 2-(hydrogen 3-hydroxy-3-methylpentanedioate), (2α,3β,12α,24R)-4-Carboxylato-3-hydroxy-3-methylbutanoic acid (24R)-3β,12α,24,25-tetrahydroxy-5α-lanost-8-en-2α-yl ester
Database identifiers
- CAS
126882-55-1- PubChem CID
- 196808
- ChEBI
CHEBI:168291
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 165 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 11
- Heavy atoms
- 45
- Formal charge
- 0
- Complexity
- 1,190
Physicochemical properties
- Boiling point
- 767.6 · 767.6±60.0 °C(Predicted)
- Density
- 1.21 · 1.21±0.1 g/cm3(Predicted)
- pka
- 4.23 · 4.23±0.10(Predicted)
Chemistry & industry
Applications
DescriptionFasciculic acid B is the ester of fasciculol B & 3-hydroxy-3-methylglutaric acid; calmodulin antagonist from mushroom Naematoloma fasciculare.
UsesFasciculic acid B is a steroid that can be isolated from Hypholoma lateritium. Fasciculic acid B has antiinflammatory and calmodulin antagonistic activity[1][2].
Additional notes
DefinitionChEBI: Fasciculic acid B is a triterpenoid.
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