Vomilenine (BioCAD00000019412)

plant natural products

Metabolite Card

Formula: C21H22N2O3 (350.163)
SMILES: [H][C@@]12C[C@]3([H])N([C@H]4C[C@@]5([C@H](OC(C)=O)C14)c1ccccc1N=C35)[C@H](O)\\C2=C\\C

Synonyms [en]

Vomilenine; 21alpha-hydroxy-22-norajmala-1,19-dien-17alpha-yl acetate; [(1R,10S,12R,13E,14R,16S,18R)-13-ethylidene-14-hydroxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6,8-tetraen-18-yl] acetate; C9L2GUG8W2; 6880-50-8; Raucaffriline

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Vomilenine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000019412). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

An indole alkaloid that is vinorine bearing a hydroxy substituent at position 21." []

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 6880-50-8
  • PubChem: 11953806
  • PubChem: 13579071
  • PubChem: 163187496
  • PubChem: 5479072
  • PubChem: 91820485
  • ChEBI: ChEBI:16408
  • KEGG: C01761
  • BioCyc: VOMILENINE
  • NCBI MeSH: vomilenine
  • Wikipedia: Vomilenine
  • Metlin: METLIN_64343
  • Coconut NaturalProduct: CNP0359646.1
  • Coconut NaturalProduct: CNP0359646.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03703 3.2.1.125 raucaffricine beta-D-glucohydrolase
KEGG:R05877 1.14.14.104 vinorine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (21alpha-hydroxylating)
KEGG:R05878 1.5.1.32 1,2-dihydrovomilenine:NADP+ oxidoreductase
KEGG:R05882 2.4.1.219 UDP-glucose:vomilenine 21-O-beta-D-glucosyltransferase
KEGG:R13383 1.3.1.73 (20S)-19,20-dihydrovomilenine:NADP+ 19,20-oxidoreductase
Rhea:RHEA:14558 3.2.1.125 raucaffricine + H2O => vomilenine + D-glucose
Rhea:RHEA:14559 3.2.1.125 vomilenine + D-glucose => raucaffricine + H2O
Rhea:RHEA:14560 3.2.1.125 raucaffricine + H2O <=> vomilenine + D-glucose
Rhea:RHEA:16410 1.5.1.32 (2R)-1,2-dihydrovomilenine + NADP+ => vomilenine + NADPH + H+
Rhea:RHEA:16411 1.5.1.32 vomilenine + NADPH + H+ => (2R)-1,2-dihydrovomilenine + NADP+
Rhea:RHEA:16412 1.5.1.32 (2R)-1,2-dihydrovomilenine + NADP+ <=> vomilenine + NADPH + H+
Rhea:RHEA:17258 1.14.14.104 vinorine + reduced [NADPH—hemoprotein reductase] + O2 => vomilenine + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:17259 1.14.14.104 vomilenine + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => vinorine + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:17260 1.14.14.104 vinorine + reduced [NADPH—hemoprotein reductase] + O2 <=> vomilenine + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:19386 2.4.1.219 vomilenine + UDP-α-D-glucose => raucaffricine + UDP + H+
Rhea:RHEA:19387 2.4.1.219 raucaffricine + UDP + H+ => vomilenine + UDP-α-D-glucose
Rhea:RHEA:19388 2.4.1.219 vomilenine + UDP-α-D-glucose <=> raucaffricine + UDP + H+
Rhea:RHEA:79636 (20S)-19,20-dihydrovomilenine + NADP+ => vomilenine + NADPH + H+
Rhea:RHEA:79637 vomilenine + NADPH + H+ => (20S)-19,20-dihydrovomilenine + NADP+
Rhea:RHEA:79638 (20S)-19,20-dihydrovomilenine + NADP+ <=> vomilenine + NADPH + H+
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