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> Main
CHEBI:142075 - tabernaemontanine
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ChEBI Ontology
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ChEBI Name
tabernaemontanine
ChEBI ID
CHEBI:142075
Definition
A monoterpenoid indole alkaloid with formula C
21
H
26
N
2
O
3
, isolated from several species of
Tabernaemontana
.
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
C21H26N2O3
Net Charge
0
Average Mass
354.444
Monoisotopic Mass
354.19434
InChI
InChI=1S/C21H26N2O3/c1-
4-
12-
11-
23(2)
17-
9-
15-
13-
7-
5-
6-
8-
16(13)
22-
20(15)
18(24)
10-
14(12)
19(17)
21(25)
26-
3/h5-
8,12,14,17,19,22H,4,9-
11H2,1-
3H3/t12-
,14+,17+,19+/m1/s1
InChIKey
FFVRRQMGGGTQRH-DTPILHQWSA-N
SMILES
CC[C@@H]1CN(C)[C@]2(CC=3C4=CC=CC=C4NC3C(C[C@@]1([C@@]2(C(=O)OC)[H])[H])=O)[H]
Metabolite of Species
Details
Ervatamia yunnanensis
(IPNI:78987-1)
Found in aerial part
(BTO:0001658)
. See: Yang, Y., Jinming, G., and Jikai, L. ' The constituents of Ervatamia yunnanensis' (1999). Acta Botanica Yunnanica. vol 21(3), p 399-405.
Tabernaemontana coronaria
(IPNI:82068-1)
Found in bark
(BTO:0001301)
. See:
PubMed
Tabernaemontana corymbosa
(NCBI:txid1679252)
Found in leaf
(BTO:0000713)
. See:
PubMed
Tabernaemontana divaricata
(NCBI:txid52861)
See:
PubMed
Tabernaemontana elegans
(NCBI:txid761068)
Found in root
(BTO:0001188)
. See:
PubMed
Tabernaemontana elegans
(NCBI:txid761068)
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.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via
alkaloid
)
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
tabernaemontanine (
CHEBI:142075
)
has role
antineoplastic agent (
CHEBI:35610
)
tabernaemontanine (
CHEBI:142075
)
has role
apoptosis inducer (
CHEBI:68495
)
tabernaemontanine (
CHEBI:142075
)
has role
plant metabolite (
CHEBI:76924
)
tabernaemontanine (
CHEBI:142075
)
is a
alkaloid ester (
CHEBI:38481
)
tabernaemontanine (
CHEBI:142075
)
is a
methyl ester (
CHEBI:25248
)
tabernaemontanine (
CHEBI:142075
)
is a
monoterpenoid indole alkaloid (
CHEBI:65323
)
tabernaemontanine (
CHEBI:142075
)
is a
organic heterotetracyclic compound (
CHEBI:38163
)
tabernaemontanine (
CHEBI:142075
)
is a
tertiary amino compound (
CHEBI:50996
)
IUPAC Name
methyl (20β)-3-oxo-19,20-dihydrovobasan-17-oate
Synonyms
Sources
(−)-tabernaemontanine
KNApSAcK
(−)-tabernemontanine
KNApSAcK
20-epidregamine
KNApSAcK
tabernaemontanin
KNApSAcK
tabernemontanine
ChEBI
Manual Xref
Database
C00026055
KNApSAcK
View more database links
Registry Numbers
Types
Sources
2134-98-7
CAS Registry Number
KNApSAcK
32846872
Reaxys Registry Number
Reaxys
Citations
Types
Sources
13740864
PubMed citation
Europe PMC
17253850
PubMed citation
Europe PMC
19525111
PubMed citation
Europe PMC
26169128
PubMed citation
Europe PMC
28189906
PubMed citation
Europe PMC
28423921
PubMed citation
Europe PMC
29758521
PubMed citation
Europe PMC
Last Modified
06 March 2020