Basic information
- CAS
4781-58-2- Standard SMILES
COc1ccc(C[C@@H]2NCCc3cc(OC)c(O)cc32)cc1O- InChIKey
FVEMXQCEJGGXJB-AWEZNQCLSA-N- Molecular formula
- C18H21NO4
- Average molar mass
- 315.4 g/mol
- Monoisotopic mass
- 315.14705815
Overview
(S)-norreticuline is a norreticuline. It has a role as an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor. It is a conjugate base of a (S)-norreticuline(1+). It is an enantiomer of a (R)-norreticuline.
Names & identifiers
- Preferred name
- (S)-Norreticuline
- IUPAC
- (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
- English name
- Nor Reticuline
- Molecular formula
- C18H21NO4
- Molecular weight
- 315.36
Names & synonyms
(S)-Norreticuline4781-58-2(-)-Norreticuline(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-olCHEBI:28611DTXSID50331558(1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol(1S)-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol11-((4-hydroxy-3-methoxy-phenyl)methyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol11-[(4-hydroxy-3-methoxy-phenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-olRefChem:70504DTXCID50282652
Show more names
7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-, (1S)-
Nor Reticuline2-Demethylreticuline(-)-(S)-N-Norreticuline(1S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-7-isoquinolinolS-NorreticulineCHEMBL349584orb1989858SCHEMBL17285807
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 71 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 380
Physicochemical properties
- Boiling point
- 519.5 · 519.5±50.0 °C(Predicted)
- Density
- 1.234 · 1.234±0.06 g/cm3(Predicted)
- pka
- 9.95 · 9.95±0.10(Predicted)
Chemistry & industry
Applications
UsesReticuline (R188500) analog. (S)-Norreticuline is the precursor for the biosynthesis of Erythrina alkaloids. (S)-Norreticuline and (S)-reticuline stimulated the proliferation of cultured cells from murine hair.
Upstream & downstream products
Downstream products
Suppliers7 total
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Additional notes
Related reactions
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Compound notes
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