Basic information
- CAS
76-28-8- Standard SMILES
C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2[C@H](O)C[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O- InChIKey
FLMSQRUGSHIKCT-DDZQJACLSA-N- Molecular formula
- C23H34O5
- Average molar mass
- 390.5 g/mol
- Monoisotopic mass
- 390.24062418
Overview
Sarmentogenin is a member of the class of cardenolides that is 5beta-card-20(22)-enolide which is substituted by hydroxy groups at the 3beta, 11alpha, and 14beta positions. It has a role as a plant metabolite. It is an 11alpha-hydroxy steroid, a 3beta-hydroxy steroid, a 14beta-hydroxy steroid and a member of cardenolides. It derives from a hydride of a 5beta-cardanolide.
Names & identifiers
- Preferred name
- Sarmentogenin
- IUPAC
- 3-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
- English name
- 11α-Hydroxydigitoxigenin
- Molecular formula
- C23H34O5
- Molecular weight
- 390.51
Names & synonyms
Sarmentogenin76-28-811-alpha-HydroxydigitoxigeninEX5655UIRZ3beta,11alpha,14-Trihydroxy-5beta-card-20(22)-enolideCHEBI:37665DTXSID808786433-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-oneCard-20(22)-enolide, 3,11,14-trihydroxy-, (3beta,5beta,11alpha)-3-((3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-2H-furan-5-oneRefChem:1098352DTXCID101016685
Show more names
11α-Hydroxydigitoxigenin3β,11α,14-Trihydroxy-5β,14β-card-20(22)-enolideCard-20(22)-enolide, 3,11,14-trihydroxy-, (3β,5β,11α)-
SARMENTOGENIN [MI]UNII-EX5655UIRZSCHEMBL1230965CHEMBL10758145-beta-CARD-20(22)-ENOLIDE, 3-beta,11-alpha,14-TRIHYDROXY-11.ALPHA.-HYDROXYDIGITOXIGENINNS00094829Sarmentogenin (11-alpha-Hydoxydigitoxigenin)
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 87 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 718
Physicochemical properties
- Melting point
- 278 · 278-282°; melting at 258°
- alpha
- 19 · D19 +21.1 ± 4° (c = 0.521 in methanol)
- Boiling point
- 435.71 °C · 435.71°C (rough estimate)
- Density
- 1.0639 · 1.0639 (rough estimate)
- refractive index
- 1.609 · 1.6090 (estimate)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5655 UIRZ · EX5655UIRZ
Chemistry & industry
Suppliers1 total
湖州展舒生物科技有限公司0572-8889530 18167260939 · [email protected]
Additional notes
DefinitionChEBI: A member of the class of cardenolides that is 5beta-card-20(22)-enolide which is substituted by hydroxy groups at the 3beta, 11alpha, and 14beta positions.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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