Basic information
- Standard SMILES
CC[C@H]1C[C@@H]2CN3CCc4c([nH]c5ccc(OC)cc45)[C@](C(=O)OC)(C2)[C@H]13- InChIKey
MMAYTCMMKJYIAM-RUGRQLENSA-N- Molecular formula
- C22H28N2O3
- Average molar mass
- 368.5 g/mol
- Monoisotopic mass
- 368.20999276
Overview
(-)-voacangine is a monoterpenoid indole alkaloid with formula C22H28N2O3, isolated from several plant species. It has a role as an antineoplastic agent, an angiogenesis inhibitor and a plant metabolite. It is a methyl ester, an organic heteropentacyclic compound, an alkaloid ester, a tertiary amino compound and a monoterpenoid indole alkaloid. It is a conjugate base of a (-)-voacangine(1+).
Names & identifiers
- Preferred name
- Voacangine
- IUPAC
- methyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
Names & synonyms
Voacangine(-)-VoacangineCarbomethoxyibogaine510-22-512-Methoxyibogamine-18-carboxylic acid methyl ester9SY76D3YUKCHEBI:141966methyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylateIbogamine-18-carboxylic acid, 12-methoxy-, methyl estermethyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylateRefChem:194597methyl (1S,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
Show more names
methyl 17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylateCHEMBL182120methyl (6xi)-12-methoxy-2alpha-ibogamine-18-carboxylatemethyl ethyl(methoxy)[?]carboxylateDTXSID50965276MMAYTCMMKJYIAM-RUGRQLENSA-NMethyl 12-methoxyibogamine-18-carboxylateUNII-9SY76D3YUK
Database identifiers
- CAS
510-22-5- PubChem CID
- 73255
- DTXSID
DTXSID50965276- ChEMBL
CHEMBL182120- ChEBI
CHEBI:141966- EC Number
- 687-877-9
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 54.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 598
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Related reactions
1 records
Linked notes
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