Stephavanine
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Basic information
- CAS
33116-33-5- Standard SMILES
COc1cc(C(=O)OC2CC34CCNC35CC(OC5(OC)C2O)c2cc3c(cc24)OCO3)ccc1O- InChIKey
BTDVYOKUHWMJJD-UHFFFAOYSA-N- Molecular formula
- C26H27NO9
- Average molar mass
- 497.5 g/mol
- Monoisotopic mass
- 497.16858144
Names & identifiers
- Preferred name
- Stephavanine
- IUPAC
- (15-hydroxy-14-methoxy-5,7,21-trioxa-20-azahexacyclo[11.4.3.111,14.01,13.02,10.04,8]henicosa-2,4(8),9-trien-16-yl) 4-hydroxy-3-methoxybenzoate
- English name
- 8β,10β-Epoxy-8-methoxy-2,3-[methylenebis(oxy)]hasubanan-6β,7β-diol 6-(4-hydroxy-3-methoxybenzoate)
- Molecular formula
- C26H27NO9
- Molecular weight
- 497.49
Names & synonyms
STEPHAVANINE33116-33-5DTXSID20329583RefChem:185569DTXCID40280682NSC135026(15-hydroxy-14-methoxy-5,7,21-trioxa-20-azahexacyclo[11.4.3.111,14.01,13.02,10.04,8]henicosa-2,4(8),9-trien-16-yl) 4-hydroxy-3-methoxybenzoateCHEMBL1992988IBA11633AKOS032948175NSC-1350268beta,10beta-Epoxy-8-methoxy-2,3-[methylenebis(oxy)]hasubanan-6beta,7beta-diol 6-(4-hydroxy-3-methoxybenzoate)
Show more names
NSC 1350268β,10β-Epoxy-8-methoxy-2,3-[methylenebis(oxy)]hasubanan-6β,7β-diol 6-(4-hydroxy-3-methoxybenzoate)Hasubanan-6,7-diol, 8,10-epoxy-8-methoxy-2,3-[methylenebis(oxy)]-, 6-(4-hydroxy-3-methoxybenzoate), (6β,7β,8β,10β)- (9CI)
DA-78042[hydroxy(methoxy)[?]yl] 4-hydroxy-3-methoxy-benzoate(15-hydroxy-14-methoxy-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14.0^{1,13.0^{2,10.0^{4,8]henicosa-2,4(8),9-trien-16-yl) 4-hydroxy-3-methoxybenzoate3-Hydroxy-4-methoxy-1,2,3,4,5,6-hexahydro-4a,11b-(epiminoethano)-4,6-epoxyphenanthro[2,3-d][1,3]dioxol-2-yl 4-hydroxy-3-methoxybenzoate3-Hydroxy-4-methoxy-1,2,3,4,5,6-hexahydro-9H-4a,11b-(epiminoethano)-4,6-epoxyphenanthro[2,3-d][1,3]dioxol-2-yl 4-hydroxy-3-methoxybenzoate
Database identifiers
- CAS
33116-33-5- PubChem CID
- 421509
- DTXSID
DTXSID20329583- ChEMBL
CHEMBL1992988
Properties
Computed structural propertiesFilling in
- XLogP
- 1.6
- Topological polar surface area
- 125 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 905
Physicochemical properties
- Melting point
- 229 · 229-2300 C
- Boiling point
- 702.1 · 702.1±60.0 °C(Predicted)
- Density
- 1.55 · 1.55±0.1 g/cm3(Predicted)
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Powder
- pka
- 8.15 · 8.15±0.20(Predicted)
Chemistry & industry
Applications
DescriptionA further Stephania alkaloid, this base occurs in the rhizomes of S. abyssinica Walp. It has [α]32D + 30° (c 0.90, pyridine) and gives a series if crystalline salts including the hydrochloride, m.p. 2l7-8°C; hydrobromide, m.p. 191-2°C (dec.) and the tria cetyl derivative, m.p. 189-190°C. On hydrolysis, the alkaloid yields 3-methoxy-4-hydroxybenzoic acid.
UsesStephavanine is a compound isolated from the roots of Stephania abyssinica[1].
Related reactions
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Compound notes
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