CHEBI:9479 - tetrahydroalstonine

ChEBI IDCHEBI:9479
ChEBI Nametetrahydroalstonine
Stars
DefinitionA heteropentacyclic compound that is (20α)-16,17-didehydro-18-oxayohimban which is substituted at position 16 by a methoxycarbonyl group and at position 19 by a methyl group. It is a metabolite found in several plant species.
Last Modified17 August 2023
DownloadsMolfile
FormulaC21H24N2O3
Net Charge0
Average Mass352.434
Monoisotopic Mass352.17869
SMILES[H][C@@]12C[C@]3([H])C(C(=O)OC)=CO[C@@H](C)[C@]3([H])CN1CCc1c2nc2ccccc12
InChIInChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19-/m0/s1
InChIKeyGRTOGORTSDXSFK-DLLGKBFGSA-N
Species of MetaboliteComponentSourceComments
Leuconotis griffithii (IPNI:79773-1) bark (BTO:0001301) PubMed (23647487) Isolated from stem bark.
Kopsia jasminiflora (IPNI:79503-1) bark (BTO:0001301) Article (Kitajima, M., Anbe, M., Kogure, N., Wongseripipatana, S. and Takayama, H. (2014) Indole alkaloids from Kopsia jasminiflora. Tetrahedron, 70(47), 9099-9106.) Isolated from stem bark.
Rhazya stricta (ncbitaxon:396313) - PubMed (26694342) Isolated from hairy root culture.
Alstonia rostrata (ncbitaxon:1679253) bark (BTO:0001301) PubMed (26125941)
Kopsia pauciflora (ncbitaxon:1037435) bark (BTO:0001301) PubMed (26717050) Isolated from stem bark
Mappianthus iodoides (ncbitaxon:210342) stem (BTO:0001300) PubMed (29101786)
Uncaria (ncbitaxon:43574) - Article (Chan, K.C. (1969) The stereochemistry of pteropodine and isopteropodine. Phytochemistry, 8(1), 219-222.) Isolated from unknown Uncaria species.
Rauvolfia obscura (IPNI:81602-1) stem (BTO:0001300) Article (Timmins, P. and Court, W.E. (1976) Stem alkaloids of Rauwolfia obscura. Phytochemistry, 15(5), 733-735.)
Amsonia elliptica (ncbitaxon:403098) seed (PO:0009010) Article (Aimi, N., Asada, Y., Sakai, S.I. and Haginiwa, J. (1978) Studies on plants containing indole alkaloids. VII. Isolation of several aspidosperma-and vincamine-type alkaloids from the seeds of Amsonia elliptica ROEM. et SCHULT. Chem. Pharm. Bull., 26(4), 1182-1187.)
Rauvolfia volkensi (IPNI:81672-1)
bark (BTO:0001301) Article (Akinloye, B.A. and Court, W.E. (1979) Stem bark alkaloids of Rauwolfia volkensii. Planta Medica, 37(12), 361-366.) Isolated from stem bark.
leaf (BTO:0000713) Article (Akinloye, B.A. and Court, W.E. (1980) Leaf alkaloids of Rauwolfia volkensii. Phytochemistry, 19(2), 307-311.)
Uncaria attenuata (ncbitaxon:1840405) leaf (BTO:0000713) Article (Ponglux, D., Supavita, T., Verpoorte, R. and Phillipson, D. (1980) Alkaloids of Uncaria attenuata from Thailand. Phytochemistry, 19(9), 2013-2016.)
Rauvolfia vomitoria (IPNI:81673-1) leaf (BTO:0000713) Article (Amer, M.M. and Court, W.E. (1980) Leaf alkaloids of Rauwolfia vomitoria. Phytochemistry, 19(8), 1833-1836.)
Alstonia undulata (IPNI:76601-1) bark (BTO:0001301) Article (Guillaume, D., Morfaux, A.M., Richard, B., Massiot, G., Olivier, L.L.M., Pusset, J. and Sévenet, T. (1984) Some alkaloids of Alstonia undulata. Phytochemistry, 23(10), 2407-2408.) Isolated from root bark.
Amsonia brevifolia (IPNI:30100631-2) whole plant (BTO:0001461) Article (Sharma, P., Shirataki, Y. and Cordell, G.A. (1988) Alkaloids of Amsonia brevifolia. Phytochemistry, 27(11), 3649-3652.)
Kopsia griffithii (ncbitaxon:1750996) leaf (BTO:0000713) Article (Kam, T.S. and Sim, K.M. (1998) Alkaloids from Kopsia griffithii. Phytochemistry, 47(1), 145-147.)
Kopsia dasyrachis (IPNI:79494-1) stem (BTO:0001300) Article (Kam, T.S., Subramaniam, G. and Chen, W. (1999) Alkaloids from Kopsia dasyrachis. Phytochemistry, 51(1), 159-169.)
Catharanthus roseus (ncbitaxon:4058) cell suspension culture (BTO:0000221) Article (Kohl, W., Witte, B. and Hofle, G. (1981) Alkaloide aus Catharanthus roseus-Zellkulturen, II / Alkaloids from Catharanthus roseus Tissue Cultures, II, Z. Naturforsch., 86b, 1153-1162.)
Kopsia singapurensis (ncbitaxon:1751000) bark (BTO:0001301) PubMed (17939738) Isolated from stem bark.
Kopsia arborea (IPNI:79490-1) bark (BTO:0001301) PubMed (17665953) Isolated from stem bark.
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
tetrahydroalstonine (CHEBI:9479) has role plant metabolite (CHEBI:76924)
tetrahydroalstonine (CHEBI:9479) is a methyl ester (CHEBI:25248)
tetrahydroalstonine (CHEBI:9479) is a organic heteropentacyclic compound (CHEBI:38164)
tetrahydroalstonine (CHEBI:9479) is a yohimban alkaloid (CHEBI:27358)
tetrahydroalstonine (CHEBI:9479) is conjugate base of tetrahydroalstonine(1+) (CHEBI:142526)
Incoming Relation(s)
tetrahydroalstonine(1+) (CHEBI:142526) is conjugate acid of tetrahydroalstonine (CHEBI:9479)
IUPAC Name 
methyl (19α,20α)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
Synonyms  Source
tetrahydroalstonineKEGG COMPOUND
methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylateChEBI
Manual XrefsDatabases
C11682KEGG COMPOUND
C00025214KNApSAcK
US3969521Patent
Registry NumbersSources
Reaxys:97270Reaxys
CAS:6474-90-4KEGG COMPOUND
CAS:6474-90-4ChemIDplus
Citations