(+)-Pisatin
Basic information
- CAS
469-01-2- Standard SMILES
COc1ccc2c(c1)OC[C@]1(O)c3cc4c(cc3O[C@H]21)OCO4- InChIKey
LZMRDTLRSDRUSU-SJORKVTESA-N- Molecular formula
- C17H14O6
- Average molar mass
- 314.29 g/mol
- Monoisotopic mass
- 314.07903816
Overview
(+)-pisatin is a member of the class of pterocarpans that is the 3-O-methyl ether of (+)-6a-hydroxymaackiain (the 6aR,12aR stereoisomer). A phytoalexin found in pods of garden peas (Pisum sativum) and other plants of the pea family, including Tephrosia candida. It has a role as a phytoalexin and a plant metabolite. It is a member of pterocarpans, a tertiary alcohol and an aromatic ether. It is functionally related to a (+)-6a-hydroxymaackiain.
Names & identifiers
- Preferred name
- (+)-Pisatin
- IUPAC
- (1R,12R)-16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-1-ol
- English name
- PISATIN
- Molecular formula
- C17H14O6
- Molecular weight
- 314.29
Names & synonyms
Pisatin(+)-pisatin469-01-2V6L86DZ4N36a-Hydroxy-3-methoxy-8,9-methylenedioxypterocarpanPISATIN, (+)-(1R,12R)-16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-1-olCHEBI:67347DTXSID3010248986H-(1,3)Dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-6a(12aH)-ol, 3-methoxy-, (6aR-cis)-(1R,12R)-16-methoxy-5,7,11,19-tetraoxapentacyclo(10.8.0.02,10.04,8.013,18)icosa-2,4(8),9,13(18),14,16-hexaen-1-olpisatin, (6aR-cis)-
Show more names
(+)-Pisation(6aR)-3-Methoxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-6aβ(12aβH)-ol6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-6a(12aH)-ol, 3-methoxy-, (6aR,12aR)-
RefChem:905480DTXCID301509072CHEMBL178426216-Methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-1-olUNII-V6L86DZ4N3(R,R)-PISATINMEGxp0_001256orb3178101
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 66.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 472
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Pterocarpans [PK1207]
LogP2.58
Physicochemical properties
- Melting point
- 60 · 60-61 °C
- Boiling point
- 483 · 483.0±45.0 °C(predicted)
- Density
- 1.501 · 1.501±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)
- pka
- 11.91 · 11.91±0.20(predicted)
- FDA UNII
- 6 L86DZ4N3 · V6L86DZ4N3
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that are destructive to protozoans.
Additional notes
DefinitionChEBI: A member of the class of pterocarpans that is the 3-O-methyl ether of (+)-6a-hydroxymaackiain (the 6aR,12aR stereoisomer). A phytoalexin found in pods of garden peas (Pisum sativum) and othe plants of the pea family, including Tephrosia candida.
Related reactions
2 records
Compound notes
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