CHEBI:9479 - tetrahydroalstonine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name tetrahydroalstonine
ChEBI ID CHEBI:9479
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C21H24N2O3
Net Charge 0
Average Mass 352.428
Monoisotopic Mass 352.17869
InChI InChI=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
InChIKey GRTOGORTSDXSFK-DLLGKBFGSA-N
SMILES C=1C=CC=2NC=3[C@]4(N(CCC3C2C1)C[C@@]5([C@@](C(=CO[C@H]5C)C(OC)=O)(C4)[H])[H])[H]
Metabolite of Species Details
Amsonia brevifolia (IPNI:30100631-2) Found in whole plant (BTO:0001461). See: Sharma, P., Shirataki, Y. and Cordell, G.A. (1988) Alkaloids of Amsonia brevifolia. Phytochemistry, 27(11), 3649-3652.
Alstonia undulata (IPNI:76601-1) Found in bark (BTO:0001301). Isolated from root bark. See: 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.
Kopsia arborea (IPNI:79490-1) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Kopsia dasyrachis (IPNI:79494-1) Found in stem (BTO:0001300). See: Kam, T.S., Subramaniam, G. and Chen, W. (1999) Alkaloids from Kopsia dasyrachis. Phytochemistry, 51(1), 159-169.
Kopsia jasminiflora (IPNI:79503-1) Found in bark (BTO:0001301). Isolated from stem bark. See: Kitajima, M., Anbe, M., Kogure, N., Wongseripipatana, S. and Takayama, H. (2014) Indole alkaloids from Kopsia jasminiflora. Tetrahedron, 70(47), 9099-9106.
Leuconotis griffithii (IPNI:79773-1) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Rauvolfia obscura (IPNI:81602-1) Found in stem (BTO:0001300). See: Timmins, P. and Court, W.E. (1976) Stem alkaloids of Rauwolfia obscura. Phytochemistry, 15(5), 733-735.
Rauvolfia volkensi (IPNI:81672-1) Found in bark (BTO:0001301). Isolated from stem bark. See: Akinloye, B.A. and Court, W.E. (1979) Stem bark alkaloids of Rauwolfia volkensii. Planta Medica, 37(12), 361-366.
Rauvolfia volkensi (IPNI:81672-1) Found in leaf (BTO:0000713). See: Akinloye, B.A. and Court, W.E. (1980) Leaf alkaloids of Rauwolfia volkensii. Phytochemistry, 19(2), 307-311.
Rauvolfia vomitoria (IPNI:81673-1) Found in leaf (BTO:0000713). See: Amer, M.M. and Court, W.E. (1980) Leaf alkaloids of Rauwolfia vomitoria. Phytochemistry, 19(8), 1833-1836.
Kopsia pauciflora (NCBI:txid1037435) Found in bark (BTO:0001301). Isolated from stem bark See: PubMed
Alstonia rostrata (NCBI:txid1679253) Found in bark (BTO:0001301). See: PubMed
Kopsia griffithii (NCBI:txid1750996) Found in leaf (BTO:0000713). See: Kam, T.S. and Sim, K.M. (1998) Alkaloids from Kopsia griffithii. Phytochemistry, 47(1), 145-147.
Kopsia singapurensis (NCBI:txid1751000) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Uncaria attenuata (NCBI:txid1840405) Found in leaf (BTO:0000713). See: Ponglux, D., Supavita, T., Verpoorte, R. and Phillipson, D. (1980) Alkaloids of Uncaria attenuata from Thailand. Phytochemistry, 19(9), 2013-2016.
Mappianthus iodoides (NCBI:txid210342) Found in stem (BTO:0001300). See: PubMed
Rhazya stricta (NCBI:txid396313) Isolated from hairy root culture. See: PubMed
Amsonia elliptica (NCBI:txid403098) Found in seed (PO:0009010). See: 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.
Catharanthus roseus (NCBI:txid4058) Found in cell suspension culture (BTO:0000221). See: 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.
Uncaria (NCBI:txid43574) Isolated from unknown Uncaria species. See: Chan, K.C. (1969) The stereochemistry of pteropodine and isopteropodine. Phytochemistry, 8(1), 219-222.
Roles Classification
Biological Role(s): 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.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylate ChEBI
tetrahydroalstonine KEGG COMPOUND
Manual Xrefs Databases
C00025214 KNApSAcK
C11682 KEGG COMPOUND
US3969521 Patent
View more database links
Registry Numbers Types Sources
6474-90-4 CAS Registry Number KEGG COMPOUND
6474-90-4 CAS Registry Number ChemIDplus
97270 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17340319 PubMed citation Europe PMC
19403195 PubMed citation Europe PMC
23285803 PubMed citation Europe PMC
5050366 PubMed citation Europe PMC
Last Modified
17 August 2023