Tripterifordin
Basic information
- CAS
139122-81-9- Standard SMILES
C[C@]12CCC[C@@]3(COC1=O)[C@@H]1CC[C@@H]4C[C@@]1(CC[C@@H]32)C[C@@]4(C)O- InChIKey
KLMZPLYXGZZBCX-CJSYXLNHSA-N- Molecular formula
- C20H30O3
- Average molar mass
- 318.4 g/mol
- Monoisotopic mass
- 318.21949481
Overview
Tripterifordin has been reported in Tripterygium wilfordii and Gynocardia odorata with data available.
Names & identifiers
- Preferred name
- Tripterifordin
- IUPAC
- (1R,2R,5R,6R,8S,11S,12R)-6-hydroxy-6,12-dimethyl-14-oxapentacyclo[10.3.3.15,8.01,11.02,8]nonadecan-13-one
- English name
- tripterifordin
- Molecular formula
- C20H30O3
- Molecular weight
- 318.45
Names & synonyms
Tripterifordin139122-81-9(1R,2R,5R,6R,8S,11S,12R)-6-hydroxy-6,12-dimethyl-14-oxapentacyclo[10.3.3.15,8.01,11.02,8]nonadecan-13-oneKauran-18-oic acid, 16,20-dihydroxy-, delta-lactone, (4alpha)-CHEBI:66275(1R,2R,5R,6R,8S,11S,12R)-6-hydroxy-6,12-dimethyl-14-oxapentacyclo(10.3.3.15,8.01,11.02,8)nonadecan-13-oneRefChem:933495Hypodiolide A(+/-)-Tripterifordinorb1218864orb1297182CHEMBL4203666
Show more names
HypodiolideripterifordinHydroxyodolideAntriptolactoneTripterifordin, 10 mM in DMSOKauran-18-oic acid, 16,20-dihydroxy-, δ-lactone, (4α)-inhibit,HIV,Human immunodeficiency virus,replication,Tripterifordin,anti-HIV,Inhibitor
DTXSID30930366HY-N6080TN2283AKOS040760738EBC-61690016-Hydroxy-18,20-epoxykauran-18-oneCS-0032508E87141
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 573
Physicochemical properties
- Boiling point
- 485.1 · 485.1±45.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Powder
- pka
- 15.24 · 15.24±0.40(Predicted)
- InChI
- InChI=1/C20H30O3/c1-17-7-3-8-20(12-23-16(17)21)14(17)6-9-19-10-13(4-5-15(19)20)18(2,22)11-19/h13-15,22H,3-12H2,1-2H3/t13-,14-,15+,17+,18-,19+,20+/s3
- InChIKey
- KLMZPLYXGZZBCX-VDOIHNSCNA-N
- SMILES
- [C@H]12CC[C@H]3[C@@](O)(C)C[C@]1(CC[C@@H]1[C@]4(C)CCC[C@@]21COC4=O)C3 |&1:0,3,4,8,11,12,17,r|
Chemistry & industry
Applications
UsesTripterifordin possesses significant anti-HIV replication activities in H9 lymphocyte cells with an EC50value of 3100 nM, respectively[1].
Additional notes
DefinitionChEBI: A kaurane diterpenoid that is (5beta,8alpha,13alpha)-18,20-epoxykauran-18-one substituted by a hydroxy group at position 16. Isolated from the roots of Tripterygium wilfordii, it exhibits anti HIV activity.
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