Basic information
- CAS
2810-21-1- Standard SMILES
COc1cc2c3c(c1OC)C1(C=CC(=O)C=C1)CC3NCC2- InChIKey
OGJKMZVUJJYWKO-UHFFFAOYSA-N- Molecular formula
- C18H19NO3
- Average molar mass
- 297.3 g/mol
- Monoisotopic mass
- 297.13649347
Overview
Stepharine has been reported in Stephania yunnanensis, Stephania cephalantha, and other organisms with data available.
Names & identifiers
- Preferred name
- 5',6'-Dimethoxy-2',3',8',8a'-tetrahydro-1'h,4h-spiro[cyclohexa-2,5-diene-1,7'-cyclopenta[ij]isoquinolin]-4-one
- IUPAC
- 10,11-dimethoxyspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
- English name
- (8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-one
- Molecular formula
- C18H19NO3
- Molecular weight
- 297.34836
Names & synonyms
NSC135069NSC 135069orb1680459CHEMBL1975436SCHEMBL15220038HMS1607I01CAA81021Spiro(2,5-cyclohexadiene-1,7'(1'H)-cyclopent(ij)isoquinolin)-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-, (R)-AKOS000618797AKOS021983166CCG-103003NSC-135069
Show more names
Stepharine(+)-Stepharine(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-one(8'aR)-2',3',8',8'a-Tetrahydro-5',6'-dimethoxyspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopenta[ij]isoquinoline]-4-oneSpiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-, (8'aR)-
5',6'-dimethoxy-2',3',8',8a'-tetrahydro-1'h,4h-spiro[cyclohexa-2,5-diene-1,7'-cyclopenta[ij]isoquinolin]-4-oneDA-58107NCI60_000789Spiro(2,5-cyclohexadien-1,7'(1'H)-cyclopent(ij)isoquinolin)-4-one, 2',3',8',8'a-tetrahydro-5,6-dimethoxy-, (R)-Spiro[2,7'(1'H)-cyclopent[ij]isoquinolin]-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-, (R)-
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 47.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 510
Physicochemical properties
- Melting point
- 179 · 179-181 °C
- Boiling point
- 487.1 · 487.1±45.0 °C(Predicted)
- Density
- 1.27 · 1.27±0.1 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- form
- Solid
- pka
- 8.08 · 8.08±0.20(Predicted)
- color
- Pale purple to purple
Chemistry & industry
Applications
DescriptionA spiroisoquinoline alkaloid from Stephania glabra, the base has [α]26D + 143° (c 1.88, CHCI3). It contains two methoxyl groups and an imino group and yields a crystalline N-acetyl derivative, m.p. 234-5°C; [α]24D- 80° (c 1.57, CHCI3). The N-methyl compound has been shown to be identical with Pronuciferine (q.v.).
UsesStepharine, an natural alkaloid, directly interactes with TLR4 and binds to the TLR4/MD2 complex (TLR4 inhibitor). Stepharine possesses anti-aging, anti-viral and anti-hypertensive effects[1].
Suppliers19 total
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
上海弘顺生物科技有限公司15901914505 · [email protected]
武汉市皇臻生物化工有限公司13795480948 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
四川精萃天成药物科技有限公司028-87865381 18108190480 · [email protected]
风咏生物（AbMole）021-10000000 13000000000 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
阿勒山（广州）生物科技有限公司18636736628 · [email protected]
上海研生实业有限公司021-59989018 15201736385 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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