Basic information
- CAS
82-57-5- Standard SMILES
COc1c2ccoc2cc2oc(C)cc(=O)c12- InChIKey
NZVQLVGOZRELTG-UHFFFAOYSA-N- Molecular formula
- C13H10O4
- Average molar mass
- 230.22 g/mol
- Monoisotopic mass
- 230.0579088
Overview
Visnagin is a furanochromone that is furo[3,2-g]chromen-5-one which is substituted at positions 4 and 7 by methoxy and methyl groups, respectively. Found in the toothpick-plant, Ammi visnaga. It has a role as an EC 1.1.1.37 (malate dehydrogenase) inhibitor, a vasodilator agent, an antihypertensive agent, a phytotoxin, an anti-inflammatory agent and a plant metabolite. It is a furanochromone, a polyketide and an aromatic ether. It is functionally related to a 5H-furo[3,2-g]chromen-5-one.
Names & identifiers
- Preferred name
- Visnagin
- IUPAC
- 4-methoxy-7-methylfuro[3,2-g]chromen-5-one
- English name
- VISNAGIN
- Molecular formula
- C13H10O4
- Molecular weight
- 230.22
Names & synonyms
Visnagin82-57-5DesmethoxykhellinVisnagidinVisnagine5-Methoxy-2-methylfuranochromone4-methoxy-7-methylfuro[3,2-g]chromen-5-oneNSC-100593P64438MLBWDTXSID502315094-Methoxy-7-methylfuro(3,2-g)chromen-5-oneCHEBI:10002
Show more names
VISNAGIN(P)VISNAGIN(RG)MetofuroximeVISNAGIN USP/EP/BPLABOTEST-BB LT00441024Visnagin, 10 mM in DMSO
4-methoxy-7-methylpyrano(3,2-f)(1)benzoxol-5-one4-methoxy-7-methylpyrano[3,2-f][1]benzoxol-5-oneRefChem:901992DTXCID30154000201-430-34-Methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one4-Methoxy-7-methyl-furo[3,2-g]chromen-5-oneEINECS 201-430-3
Database identifiers
- CAS
82-57-5- PubChem CID
- 6716
- DTXSID
DTXSID50231509- ChEMBL
CHEMBL45176- ChEBI
CHEBI:10002- UNII
- P64438MLBW
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 48.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 362
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Benzopyranoids [PK1311]
SpringerMaterials PropertiesChemical shift
Collision Cross Section
141.54 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
139.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 139 · 139-142 °C
- Boiling point
- 292.2 °C · 292.2°C (rough estimate)
- Density
- 1.1302 · 1.1302 (rough estimate)
- refractive index
- 1.43 · 1.4300 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
- form
- Fine Crystalline Powder
- color
- Beige
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- rtecs
- LV1420000
- hs_code
- 29162000
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Hazard statements
- H302
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionVisnagin (82-57-5) is a natural product isolated from the plant Ammi visnaga. It displays protective effects against doxorubicin-induced cardiomyopathy via inhibition of mitochondrial malate dehydrogenase resulting in a decrease in cardiomyocyte apoptosis.1
Usesantiinflammatory, neuroprotective
Upstream & downstream products
Downstream products
Suppliers50 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
郑州汇聚化工有限公司0371-53399770 18037166334 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
上海纽雀客生物科技有限公司13916276291 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
InvivoChem中国
Related reactions
3 records
Compound notes
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