3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,5R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Basic information
- CAS
127-32-2- Standard SMILES
COC1C[C@H](O[C@H]2CC[C@]3(C)C4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)C4CC[C@]3(O)C2)OC(C)[C@H]1O- InChIKey
XRWQBDJPMXRDOQ-KJVXBACWSA-N- Molecular formula
- C30H46O8
- Average molar mass
- 534.7 g/mol
- Monoisotopic mass
- 534.31926842
Names & identifiers
- Preferred name
- 3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,5R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
- IUPAC
- 3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,5R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
- English name
- Periplocymarin
- Molecular formula
- C30H46O8
- Molecular weight
- 534.68144
Names & synonyms
3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,5R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one127-32-2DTXSID709257563-[(2,6-Dideoxy-3-O-methylhexopyranosyl)oxy]-5,14-dihydroxycard-20(22)-enolide(8xi,9xi)-3beta-[(2,6-Dideoxy-3-O-methyl-beta-D-glycero-hexopyranosyl)oxy]-5,14-dihydroxy-5beta-card-20(22)-enolidePeriplocymarin3β-[(3-O-Methyl-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-5β-card-20(22)-enolide3β-[(2,6-Dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-5β-card-20(22)-enolide3β-(3-O-Methyl-2,6-dideoxy-β-D-ribo-hexopyranosyloxy)-5,14-dihydroxy-5β-cardanolide-20(22)-ene
Database identifiers
- CAS
127-32-2- PubChem CID
- 36145
- DTXSID
DTXSID70925756
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 115 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 38
- Formal charge
- 0
- Complexity
- 983
Physicochemical properties
- FDA UNII
- 9 M3584249U · 9M3584249U
Chemistry & industry
Applications
DescriptionPeriplocymarin is a class of alpha cardiac glycosides present in Xiangjiapi, which has pharmacological effects such as cardiac diuresis, anti-tumor, anti-inflammatory, and immune regulation.
UsesPeriplocymarin can increase myocardial contractility and slow down the heart rate, and is the main medicinal ingredient of Xiangjiapi.
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Compound notes
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