Tabersonine

HCID 20485
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
4429-63-4
Standard SMILES
CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32
InChIKey
FNGGIPWAZSFKCN-ACRUOGEOSA-N
Molecular formula
C21H24N2O2
Average molar mass
336.4 g/mol
Monoisotopic mass
336.18377801

Overview

Tabersonine is a monoterpenoid indole alkaloid with cytotoxic activity. It has a role as a metabolite and an antineoplastic agent. It is a methyl ester, an organic heteropentacyclic compound, an alkaloid ester and a monoterpenoid indole alkaloid. It is a conjugate base of a tabersoninium(1+).

Names & identifiers

Preferred name
Tabersonine
IUPAC
methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylate
English name
TABERSONINE
Molecular formula
C21H24N2O2
Molecular weight
336.44

Names & synonyms

Tabersonine4429-63-4TabersoninMN955K48NBAspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5alpha,12beta,19alpha)-CHEBI:16776DTXSID30196102methyl 2,3,6,7-tetradehydro-5alpha,12beta,19alpha-aspidospermidine-3-carboxylatemethyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylatemethyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2,4,6,9,13-pentaene-10-carboxylateRefChem:187087DTXCID00118593
Show more names
W 873W-873C09244TabuningabersonineIt's BoninIt's BoninBRN 3051738
224-615-0(-)-TabersonineMFCD28140545Q21099578(5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid, methyl estermethyl (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate(-)-Tabersonine; (5|A,12|A,19|A)-2,3,6,7-Tetrahydro-aspidospermidine-3-carboxylic acid methyl ester; TabersoninASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 2,3,6,7-TETRADEHYDRO-, METHYL ESTER, (5.ALPHA.,12R,19.ALPHA.)-

Database identifiers

CAS
4429-63-4
PubChem CID
20485
DTXSID
DTXSID30196102
ChEMBL
CHEMBL2011511
ChEBI
CHEBI:16776
UNII
MN955K48NB
EC Number
224-615-0
Nikkaji
J62.335K

Properties

Computed structural properties

XLogP
3.4
Topological polar surface area
41.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
25

Physicochemical properties

Melting point
196 °C · 196 °C
Boiling point
488.7 · 488.7±45.0 °C(Predicted)
Density
1.27 · 1.27±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Inert atmosphere,Store in freezer, under -20°C
solubility
Chloroform (Slightly), Ethanol (Slightly, Sonicated), Ethyl Acetate (Slightly)
form
Solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302
Precautionary statements
P264-P270-P301+P312-P330-P501

Chemistry & industry

Applications · 3 items

DescriptionThis alkaloid, found in Amsonia tabernaemontana, is difficult to obtain crystalline but the hydrochloride is readily crystallizable and has m.p. 195-6°C; [α]D - 310° (c 0.134, MeOH).

OccurrenceThe seeds of Amsonia elliptica contain this N-oxide at tabersonine.

Uses(-)-Tabersonine is one of the terpenoid indole alkaloids (TIAs) from Catharanthus roseus. (-)-Tabersonine shows hypotensive activity, anti-tumor activity, hypoglycemic, diuretic activity.

Upstream & downstream products

Downstream products

Suppliers100 total

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
成都健腾生物技术有限公司028-85159085 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]

Additional notes

DefinitionChEBI: A monoterpenoid indole alkaloid with cytotoxic activity.

Related reactions

1 records
New reaction record

Compound notes

Loading…