Cardanolide, 3,12,14-trihydroxy-, (3beta,5beta,12beta)-
Basic information
- CAS
4442-12-0- Standard SMILES
C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H]([C@@H]3COC(=O)C3)CC[C@]12O- InChIKey
MWPLZPAHTHIKQB-YNFYBLEISA-N- Molecular formula
- C23H36O5
- Average molar mass
- 392.5 g/mol
- Monoisotopic mass
- 392.25627424
Overview
20,22-dihydrodigoxigenin is a hydroxy steroid that is the 20,22-dihydro derivative of digoxigenin, consisting of 5beta-cardanolide with hydroxy groups at the 3beta-, 12beta- and 14beta-positions. It is a 3beta-hydroxy steroid, a 12beta-hydroxy steroid and a 14beta-hydroxy steroid. It is functionally related to a digoxigenin.
Names & identifiers
- Preferred name
- Cardanolide, 3,12,14-trihydroxy-, (3beta,5beta,12beta)-
- IUPAC
- (4R)-4-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]oxolan-2-one
- English name
- (5beta)-3beta,12beta,14-trihydroxycardanolide
- Molecular formula
- C23H36O5
- Molecular weight
- 392.53
Names & synonyms
20,22-Dihydrodigoxigenin4442-12-03beta,12beta,14-trihydroxy-5beta-cardanolideCHEBI:71004Cardanolide, 3,12,14-trihydroxy-, (3beta,5beta,12beta)-RefChem:918063DihydrodigoxigeninFT776QDZ4Y(4R)-4-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]oxolan-2-oneEINECS 224-666-9(5beta)-3beta,12beta,14-TrihydroxycardanolideUNII-FT776QDZ4Y
Show more names
Dihydro-Digoxigenin3β,12β,14-Trihydroxy-5β-cardanolideCardanolide, 3,12,14-trihydroxy-, (3β,5β,12β)- (9CI)5-beta-Cardanolide, 3-beta,12-beta,14-trihydroxy- (6ci,7ci,8ci)
20,22-Dihydro-digoxigeninCHEMBL4188443,12,14-TrihydroxycardanolideSCHEMBL31554973DTXSID50963217Cardanolide, 3,12,14-trihydroxy-, (3-beta,5-beta,12-beta)-NS000485825beta-Cardanolide, 3beta,12beta,14-trihydroxy-
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 87 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 665
Physicochemical properties
- Boiling point
- 579.781 · 579.781±50.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.267 · 1.267±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 14.45 · 14.450±0.70(predicted)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 776 QDZ4Y · FT776QDZ4Y
Chemistry & industry
Additional notes
DefinitionChEBI: 20,22-dihydrodigoxigenin is a hydroxy steroid that is the 20,22-dihydro derivative of digoxigenin, consisting of 5beta-cardanolide with hydroxy groups at the 3beta-, 12beta- and 14beta-positions. It is a 3beta-hydroxy steroid, a 12beta-hydroxy steroid and a 14beta-hydroxy steroid. It is functionally related to a digoxigenin.
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