Tabersonine
Tabersonine is a monoterpenoid indole alkaloid with cytotoxic activity. It has a role as an antineoplastic agent. It is the product of TS (Tabersonine synthase; carboxylesterase-like [4+2] cyclase) from dihydroprecondylocarpine acetate or Dehydrosecodine
General
Type : Indole, Alkaloid, Natural
Chemical_Nomenclature : 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
Canonical SMILES : CCC12CC(=C3C4(C1N(CC4)CC=C2)C5=CC=CC=C5N3)C(=O)OC
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
InChIKey : FNGGIPWAZSFKCN-ACRUOGEOSA-N
Other name(s) : Tabersonin, (-)-Tabersonine, MN955K48NB, CHEBI:16776, methyl 2,3,6,7-tetradehydro-5alpha,12beta,19alpha-aspidospermidine-3-carboxylate, CHEMBL2011511
MW : 336.4
Formula : C21H24N2O2
CAS_number : 4429-63-4
PubChem : 20485
UniChem : FNGGIPWAZSFKCN-ACRUOGEOSA-N
Target
Families : Tabersonine ligand of proteins in family
Plant_carboxylesterase
Protein :
catro-TS
References (3)
| Title : Evolution and diversification of carboxylesterase-like [4+2] cyclases in aspidosperma and iboga alkaloid biosynthesis - DeMars_2024_Proc.Natl.Acad.Sci.U.S.A_121_e2318586121 |
| Author(s) : DeMars MD, 2nd , O'Connor SE |
| Ref : Proc Natl Acad Sci U S A , 121 :e2318586121 , 2024 |
| PubMedID: 38319969 |
| Gene_locus related to this paper: catro-CS , catro-TS , tabib-a0a5b8x6s2 , tabib-CorS |
| Title : Biosynthesis of an Anti-Addiction Agent from the Iboga Plant - Farrow_2019_J.Am.Chem.Soc_141_12979 |
| Author(s) : Farrow SC , Kamileen MO , Caputi L , Bussey K , Mundy JEA , McAtee RC , Stephenson CRJ , O'Connor SE |
| Ref : Journal of the American Chemical Society , 141 :12979 , 2019 |
| PubMedID: 31364847 |
| Gene_locus related to this paper: tabib-TiPNAE1 , tabib-TiPNAE2 , tabib-TiPNAE3 , tabib-a0a5b8x6s2 , tabib-CorS |
| Title : Solution of the multistep pathway for assembly of corynanthean, strychnos, iboga, and aspidosperma monoterpenoid indole alkaloids from 19E-geissoschizine - Qu_2018_Proc.Natl.Acad.Sci.U.S.A_115_3180 |
| Author(s) : Qu Y , Easson M , Simionescu R , Hajicek J , Thamm AMK , Salim V , De Luca V |
| Ref : Proc Natl Acad Sci U S A , 115 :3180 , 2018 |
| PubMedID: 29511102 |
| Gene_locus related to this paper: catro-CS , catro-TS , catro-hl3 , catro-hl4 |