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Vincadifformine

HCID 94255
NotesReactions
Basic informationOverviewNames & identifiersPropertiesRelated reactionsCompound notes
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Basic information

CAS
3247-10-7
Standard SMILES
CC[C@]12CCCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32
InChIKey
GIGFIWJRTMBSRP-ACRUOGEOSA-N
Molecular formula
C21H26N2O2
Average molar mass
338.4 g/mol
Monoisotopic mass
338.19942808

Overview

(-)-vincadifformine is an aspidosperma alkaloid that is (5alpha,12beta,19alpha)-2,3-didehydroaspidospermidine which is substituted at position 3 by a methoxycarbonyl group. A natural product found in several species in the Apocynaceae (dogbane) family, including Alstonia spatulata. It has a role as an antiplasmodial drug and a plant metabolite. It is an Aspidosperma alkaloid, a methyl ester, an organonitrogen heterocyclic compound, an organic heteropentacyclic compound, a secondary amino compound and a tertiary amino compound. It is a conjugate base of a (-)-vincadifformine(1+). It is an enantiomer of a (+)-vincadifformine.

Names & identifiers

Preferred name
Vincadifformine
IUPAC
methyl (1R,12S,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylate

Names & synonyms

Vincadifformine(-)-Vincadifformine3247-10-76,7-DihydrotabersonineCHEBI:70507methyl (1R,12S,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylatemethyl (1R,12S,19S)-12-ethyl-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2,4,6,9-tetraene-10-carboxylateRefChem:934034221-823-3(+/-)-VincadifformineCHEMBL251690SCHEMBL4660755
Show more names
DTXSID20954218GIGFIWJRTMBSRP-ACRUOGEOSA-NEINECS 221-823-3NSC785180NSC815333NSC-785180NSC-815333(5alpha,12beta,19alpha)-2,3-didehydroaspidospermidine-3-carboxylic acid methyl ester

Database identifiers

CAS
3247-10-7
PubChem CID
94255
DTXSID
DTXSID20954218
ChEMBL
CHEMBL251690
ChEBI
CHEBI:70507
EC Number
221-823-3
Nikkaji
J14.889J

Properties

Computed structural properties

XLogP
3.5
Topological polar surface area
41.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
25
Formal charge
0
Complexity
629

Related reactions

1 records
New reaction record
HRID 27237 reaction equation
HRID 27237As reactantuspto-grants-1980_09

Compound notes

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