(1R)-1-(((2S,3R,11bS)-3-Ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo(a)quinolizin-2-yl)methyl)-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indol-6-ol
Basic information
- CAS
2632-29-3- Standard SMILES
CC[C@H]1CN2CCc3cc(OC)c(OC)cc3[C@@H]2C[C@@H]1C[C@H]1NCCc2c1[nH]c1ccc(O)cc21- InChIKey
JRVWIILYWSBUMC-PRUVNFMMSA-N- Molecular formula
- C29H37N3O3
- Average molar mass
- 475.6 g/mol
- Monoisotopic mass
- 475.28349205
Overview
Tubulosine is a member of the class of beta-carbolines that is tubulosan bearing methoxy groups at positions 10 and 11 and a hydroxy group at the 8' position. It is an isoquinoline alkaloid, a member of isoquinolines, a member of phenols, a secondary amino compound, a tertiary amino compound and a member of beta-carbolines. It derives from a hydride of a tubulosan.
Names & identifiers
- Preferred name
- (1R)-1-(((2S,3R,11bS)-3-Ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo(a)quinolizin-2-yl)methyl)-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indol-6-ol
- IUPAC
- (1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-ol
- English name
- tubulosine
- Molecular formula
- C29H37N3O3
- Molecular weight
- 475.62
Names & synonyms
Tubulosine2632-29-3Tubulosan-8'-ol, 10,11-dimethoxy-10,11-DimethoxytubulosanolCHEBI:9775112A6Z7SN5NSC-131547DTXSID701100319(1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-ol(1R)-1-(((2S,3R,11BS)-3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-2H-BENZO(A)QUINOLIZIN-2-YL)METHYL)-2,3,4,9-TETRAHYDRO-1H-PYRIDO(3,4-B)INDOL-6-OL(1R)-1-(((2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo(a)quinolizin-2-yl)methyl)-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indol-6-ol(1R)-1-[[(2S,3R,11bS)-3-Ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizin-2-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-ol
Show more names
RefChem:192462DTXCID301532031Marckine10,11-Dimethoxytubulosan-8'-olNSC131547(1R)-1-[[(2S,3R,11bS)-3-Ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-ol1H-PYRIDO(3,4-B)INDOL-6-OL, 1-(((2S,3R,11BS)-3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-2H-BENZO(A)QUINOLIZIN-2-YL)METHYL)-2,3,4,9-TETRAHYDRO-, (1R)-1H-Pyrido[3,4-b]indol-6-ol, 1-[[(2S,3R,11bS)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizin-2-yl]methyl]-2,3,4,9-tetrahydro-, (1R)-
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 69.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 723
Physicochemical properties
- Melting point
- 282 · 282-283 °C
- Boiling point
- 667.8 · 667.8±55.0 °C(Predicted)
- Density
- 1.27 · 1.27±0.1 g/cm3(Predicted)
- pka
- 9.78 · 9.78±0.40(Predicted)
- FDA UNII
- 112 A6Z7SN5 · 112A6Z7SN5
Chemistry & industry
Applications
DescriptionThis alkaloid is a constituent of the bark of Pogonopus tubulosus (DC.) Schumann and is laevorotatory having [α]24D - 65.9° (c 2.0, pyridine). The ultraviolet spectrum in ethanol has an absorption maximum at 281Mu with a shoulder at 225 Mu. Two methoxyl groups, a phenolic hydroxyl group and two imino groups are present, the base yielding a crystalline monoacetyl derivative, m.p. l84-6°C and the diacetyl compound, m.p. l49-l5l°C.
Additional notes
DefinitionChEBI: A member of the class of beta-carbolines that is tubulosan bearing methoxy groups at positions 10 and 11 and a hydroxy group at the 8' position.
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