Dihydroprecondylocarpine-acetate

Dihydroprecondylocarpine acetate is an organic cation which is an intermediate in the biosynthetic pathway leading to the synthesis of the monoterpenoid indole alkaloids, catharanthine and tabersonine. Leads to the formation of Dehydrosecodine an instable intermediate in the biosynthesis of aspidosperma and iboga alkaloids. It is a terpenoid indole alkaloid, a methyl ester, a dihydropyridine, a member of indoles, an alkaloid ester and an enamine. Three carboxylesterase (CXE)-like enzymes from Catharanthus roseus and Tabernanthe iboga catalyze regio- and enantiodivergent cycloaddition reactions to generate the aspidosperma (tabersonine synthase, TS) and iboga (coronaridine synthase, CorS; catharanthine synthase, CS) scaffolds from a common biosynthetic intermediate. Dehydrosecodine(1+) (CID 135398075) is a tertiary ammonium ion result from the protonation of the tertiary amino group of dehydrosecodine (the enamine form). Dehydrosecodine is the substrate and tabersonine catharanthine and carbomehtoxycleaviminium are the products of these enzyme. These later compound are substrate for aditional enzymes to give vinblastine coronaridine and ibogaine

General

Type : Indole, Alkaloid, Natural

Chemical_Nomenclature : methyl (1S,2S)-2-(acetyloxymethyl)-16-ethyl-4-aza-14-azoniatetracyclo[12.2.2.03,11.05,10]octadeca-3(11),5,7,9,14-pentaene-2-carboxylate

Canonical SMILES : CCC1C=[N+]2CCC1C(C3=C(CC2)C4=CC=CC=C4N3)(COC(=O)C)C(=O)OC

InChI : InChI=1S\/C23H29N2O4\/c1-4-16-13-25-11-9-18-17-7-5-6-8-20(17)24-21(18)23(22(27)28-3,14-29-15(2)26)19(16)10-12-25\/h5-8,13,16,19,24H,4,9-12,14H2,1-3H3\/q+1\/t16?,19-,23-\/m0\/s1

InChIKey : QXQMGTOURBIIKD-RUMUXARQSA-N

Other name(s) : dihydroprecondylocarpine acetate  ||  CHEBI:142770  ||  (6S,7S)-7-(acetoxymethyl)-5-ethyl-7-(methoxycarbonyl)-1,2,5,6,7,8-hexahydro-3,6-ethanoazonino[5,4-b]indol-3-ium


MW : 397.5

Formula : C23H29N2O4+

CAS_number :

PubChem : 135398095

UniChem : QXQMGTOURBIIKD-RUMUXARQSA-N

Target

Structures : No structure

Families : Plant_carboxylesterase

References (4)

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
Abstract :
PubMedSearch : DeMars_2024_Proc.Natl.Acad.Sci.U.S.A_121_e2318586121
PubMedID: 38319969
Gene_locus related to this paper: catro-CS , catro-TS , tabib-a0a5b8x6s2 , tabib-CorS

Title : Structural basis of cycloaddition in biosynthesis of iboga and aspidosperma alkaloids - Caputi_2020_Nat.Chem.Biol_16_383
Author(s) : Caputi L , Franke J , Bussey K , Farrow SC , Vieira IJC , Stevenson CEM , Lawson DM , O'Connor SE
Ref : Nat Chemical Biology , 16 :383 , 2020
Abstract :
PubMedSearch : Caputi_2020_Nat.Chem.Biol_16_383
PubMedID: 32066966
Gene_locus related to this paper: catro-CS , catro-TS , tabib-a0a5b8x6s2 , tabib-CorS

Title : Completion of the canonical pathway for assembly of anticancer drugs vincristine\/vinblastine in Catharanthus roseus - Qu_2019_Plant.J_97_257
Author(s) : Qu Y , Safonova O , De Luca V
Ref : Plant J , 97 :257 , 2019
Abstract :
PubMedSearch : Qu_2019_Plant.J_97_257
PubMedID: 30256480
Gene_locus related to this paper: catro-hl3 , catro-hl4

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
Abstract :
PubMedSearch : Qu_2018_Proc.Natl.Acad.Sci.U.S.A_115_3180
PubMedID: 29511102
Gene_locus related to this paper: catro-CS , catro-TS , catro-hl3 , catro-hl4