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ChEBI
> Main
CHEBI:141964 - vindolinine
Main
ChEBI Ontology
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ChEBI Name
vindolinine
ChEBI ID
CHEBI:141964
Definition
A monoterpenoid indole alkaloid with formula C
21
H
24
N
2
O
2
, isolated from several plant species.
Stars
This entity has been manually annotated by the ChEBI Team.
Submitter
Mark Williams
Supplier Information
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Molfile
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Molfile
Formula
C21H24N2O2
Net Charge
0
Average Mass
336.428
Monoisotopic Mass
336.18378
InChI
InChI=1S/C21H24N2O2/c1-
13-
19-
8-
5-
10-
23-
11-
9-
20(18(19)
23)
14-
6-
3-
4-
7-
16(14)
22-
21(13,20)
15(12-
19)
17(24)
25-
2/h3-
8,13,15,18,22H,9-
12H2,1-
2H3/t13-
,15+,18+,19+,20-
,21-
/m1/s1
InChIKey
JSLDLCGKZDUQSH-SBDPWIONSA-N
SMILES
C12=CC=CC=C1N[C@@]34[C@@]25[C@@]6([C@](C[C@H]3C(=O)OC)(C=CCN6CC5)[C@@]4([H])C)[H]
Metabolite of Species
Details
Melodinus tenuicaudatus
(IPNI:80259-1)
Found in bark
(BTO:0001301)
. See:
PubMed
Catharanthus lanceus
(NCBI:txid1750993)
Found in leaf
(BTO:0000713)
. See:
PubMed
Catharanthus trichophyllus
(NCBI:txid319559)
Found in root
(BTO:0001188)
. See:
PubMed
Catharanthus roseus
(NCBI:txid4058)
Found in leaf
(BTO:0000713)
. See:
PubMed
Roles Classification
Chemical Role
(s):
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Br
o
nsted acid).
(via
organic amino compound
)
Biological Role
(s):
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via
alkaloid
)
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
vindolinine (
CHEBI:141964
)
has role
plant metabolite (
CHEBI:76924
)
vindolinine (
CHEBI:141964
)
is a
methyl ester (
CHEBI:25248
)
vindolinine (
CHEBI:141964
)
is a
monoterpenoid indole alkaloid (
CHEBI:65323
)
vindolinine (
CHEBI:141964
)
is a
organic heteropentacyclic compound (
CHEBI:38164
)
vindolinine (
CHEBI:141964
)
is a
tertiary amino compound (
CHEBI:50996
)
IUPAC Name
methyl (3β,5α,12β,19α,20
R
)-
6,7-
didehydro-
2,20-
cycloaspidospermidine-
3-
carboxylate
Synonyms
Sources
(−)-vindolinine
KNApSAcK
Vindolinin
ChEBI
Manual Xref
Database
C00024615
KNApSAcK
View more database links
Registry Numbers
Types
Sources
52849
Reaxys Registry Number
Reaxys
5980-02-9
CAS Registry Number
ChemIDplus
Citations
Types
Sources
15682277
PubMed citation
Europe PMC
17265274
PubMed citation
Europe PMC
24241871
PubMed citation
Europe PMC
26854826
PubMed citation
Europe PMC
4473533
PubMed citation
Europe PMC
4530263
PubMed citation
Europe PMC
5677682
PubMed citation
Europe PMC
Last Modified
11 September 2018
General Comment
2018-09-11
Relevant article: Werner Kohl, Barbara Witte und Gerhard Höfle. Alkaloide aus Catharanthus roseus-Zellkulturen (1981). Z. Naturforsch. 86b, p 1153-1162.