Chemistry:Tabersonine

Tabersonine

Names
IUPAC name Methyl 2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate
Systematic IUPAC name Methyl (3aR,3a1S,10bR)-3a-ethyl-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Identifiers
CAS Number	4429-63-4 Y 29479-00-3 (hydrochloride) Y
3D model (JSmol)	Interactive image
ChemSpider	19292
PubChem CID	20485
UNII	MN955K48NB Y
InChI InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1 Key: FNGGIPWAZSFKCN-ACRUOGEOSA-N InChI=1/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1 Key: FNGGIPWAZSFKCN-ACRUOGEOBF
SMILES CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)c5ccccc5N3)C(=O)OC
Properties
Chemical formula	C21H24N2O2
Molar mass	336.435 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tracking categories (test):

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Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also in the genus Voacanga (both taxa belonging to the alkaloid-rich family Apocynaceae). Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase (T16H) to form 16-hydroxytabersonine. The enzyme leading to its formation is currently unknown. Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.

See also

• Conopharyngine
• Tabernanthine
• Vinblastine