Mahanimbine
Basic information
- CAS
21104-28-9- Standard SMILES
CC(C)=CCCC1(C)C=Cc2c(c(C)cc3c2[nH]c2ccccc23)O1- InChIKey
HTNVFUBCWIYPJN-UHFFFAOYSA-N- Molecular formula
- C23H25NO
- Average molar mass
- 331.4 g/mol
- Monoisotopic mass
- 331.19361442
Overview
Mahanimbine is a member of carbazoles.
Names & identifiers
- Preferred name
- Mahanimbine
- IUPAC
- 3,5-dimethyl-3-(4-methylpent-3-enyl)-11H-pyrano[3,2-a]carbazole
- English name
- Mahanimbine
- Molecular formula
- C23H25NO
- Molecular weight
- 331.45
Names & synonyms
Mahanimbine21104-28-93,5-dimethyl-3-(4-methylpent-3-enyl)-11H-pyrano[3,2-a]carbazoleDTXSID6010350723,5-dimethyl-3-(4-methylpent-3-enyl)-11H-pyrano(3,2-a)carbazoleRefChem:800715DTXCID501519536(+)-Mahanimbine3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazoleCHEBI:6646NSC186884Pyrano(3,2-a)carbazole, 3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)-, (+)-
Show more names
Mahanimbine-RMMahanimbine (Standard)(+)-3,11-Dihydro-3,5-dimethyl-3-(4-methyl-3-penten-1-yl)pyrano[3,2-a]carbazole
24948-14-9(+)-3,11-Dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)pyrano[3,2-a]carbazoleMahanimbin(+)-3,11-Dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)pyrano(3,2-a)carbazolePyrano[3,2-a]carbazole, 3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-penten-1-yl)-, (3S)-Rel-(+)-MahanimbineC09220CHEMBL495873
Database identifiers
- CAS
21104-28-9- PubChem CID
- 167963
- DTXSID
DTXSID601035072- ChEMBL
CHEMBL495873- ChEBI
CHEBI:6646- EC Number
- 106-616-7
- Nikkaji
- J15.919K、J3.352.656C
Properties
Computed structural properties
- XLogP
- 6.6
- Topological polar surface area
- 25 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 548
Experimental & physicochemical properties
Melting Point94 - 95 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 94 · 94-95 °C
- Boiling point
- 502.6 · 502.6±39.0 °C(Predicted)
- Density
- 1.109 · 1.109
- solubility
- 10 mM · DMSO: 10 mM
- pka
- 17.31 · 17.31±0.40(Predicted)
- Stability
- Light Sensitive
- InChI
- InChI=1S/C23H25NO/c1-15(2)8-7-12-23(4)13-11-18-21-19(14-16(3)22(18)25-23)17-9-5-6-10-20(17)24-21/h5-6,8-11,13-14,24H,7,12H2,1-4H3/t23-/m0/s1
- InChIKey
- HTNVFUBCWIYPJN-QHCPKHFHSA-N
- SMILES
- N1C2=C(C=CC=C2)C2=C1C1C=C[C@](C)(CC/C=C(\C)/C)OC=1C(C)=C2
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
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, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- risk_code
- 53
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H319-H413
- Precautionary statements
- P264-P270-P273-P280-P301+P312-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
DescriptionThe leaves of Murraya koenigii Spreng. also furnish this crystalline alkaloid which is dextrorotatory with [α]D + 52° (CHCI3). The ultraviolet spectrum exhibits several absorption maxima occurring at 227, 288,300,315,328,343 and 357 mil. It furnishes a crystalline picrate as pale yellow needles, m.p. 142°C and on catalytic reduction gives the dihydro derivative, m.p. 101°C and finally the tetrahydro compound, m.p. 108°C. Spectroscopic and chemical data support the structure given above.
UsesMahanimbine is an orally active alkaloid from Murraya koenigii. Mahanimbine inhibits progression of high-fat diet (HFD)-induced metabolic complications in mice[1].
Additional notes
DefinitionChEBI: Mahanimbine is a member of carbazoles.
Related reactions
1 records
Compound notes
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