(6aR,11aR)-3,9-Dimethoxy-6H-benzofuro(3,2-c)(1)benzopyran-6a(11aH)-ol
Basic information
- CAS
3187-52-8- Standard SMILES
COc1ccc2c(c1)OC[C@]1(O)c3ccc(OC)cc3O[C@H]21- InChIKey
VVPGAJNPGZZNBM-SJORKVTESA-N- Molecular formula
- C17H16O5
- Average molar mass
- 300.3 g/mol
- Monoisotopic mass
- 300.09977361
Overview
(-)-Variabilin is a member of pterocarpans.
Names & identifiers
- Preferred name
- (6aR,11aR)-3,9-Dimethoxy-6H-benzofuro(3,2-c)(1)benzopyran-6a(11aH)-ol
- IUPAC
- (6aR,11aR)-3,9-dimethoxy-6,11a-dihydro-[1]benzofuro[3,2-c]chromen-6a-ol
- English name
- variabilin
- Molecular formula
- C17H16O5
- Molecular weight
- 300.31
Names & synonyms
(-)-Variabilin3187-52-86a-Hydroxy-3,9-dimethoxypterocarpan(6aR,11aR)-3,9-dimethoxy-6,11a-dihydro-[1]benzofuro[3,2-c]chromen-6a-olDTXSID20331964(6aR,11aR)-3,9-dimethoxy-6,11a-dihydro-(1)benzofuro(3,2-c)chromen-6a-olRefChem:934873DTXCID00283058(6aR,11aR)-3,9-Dimethoxy-6H-benzofuro(3,2-c)(1)benzopyran-6a(11aH)-ol370102-93-5HomopisatinCHEBI:123
Show more names
variabilin(+)-HomopisatinVariabilin(Dalbergia)(6aR)-3,9-Dimethoxy-6H-benzofuro[3,2-c][1]benzopyran-6aβ(11aβH)-ol6H-Benzofuro[3,2-c][1]benzopyran-6a(11aH)-ol, 3,9-dimethoxy-, (6aR,11aR)-
LMPK12070130Q27105251(6aR,11aR)-3,9-Dimethoxy-6H-[1]benzofuro[3,2-c][1]benzopyran-6a(11aH)-ol
Database identifiers
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 57.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 416
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Pterocarpans [PK1207]
Chemistry & industry
Applications
UsesVariabilin (Homopisatin) is a potent RGD-containing antagonist of glycoprotein IIb-IIIa and platelet aggregation inhibitor from the hard tick Dermacentor variabilis. Variabilin potently inhibits platelet aggregation induced by the platelet agonists ADP, collagen, and thrombin receptor peptide SFLLRNP. Variabilin also blocks platelet adhesion to immobilized Fg. In addition, Variabilin inhibits binding of purified human GPIIb-IIIa to immobilized Fg[1][2].
Additional notes
DefinitionChEBI: (-)-Variabilin is a member of pterocarpans.
Related reactions
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Compound notes
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