CHEBI:28487 - reserpine

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ChEBI Name reserpine
ChEBI ID CHEBI:28487
Definition An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8808, CHEBI:26531
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Formula C33H40N2O9
Net Charge 0
Average Mass 608.67870
Monoisotopic Mass 608.273
InChI InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
InChIKey QEVHRUUCFGRFIF-MDEJGZGSSA-N
SMILES [H][C@]12C[C@@H](OC(=O)c3cc(OC)c(OC)c(OC)c3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCc3c1[nH]c1cc(OC)ccc31)C2
Metabolite of Species Details
Rauvolfia vomitoria (NCBI:403115) See: DOI
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): first generation antipsychotic
Antipsychotic drugs which can have different modes of action but which tend to be more likely than second generation antipsychotics to cause extrapyramidal motor control disabilities such as body rigidity or Parkinson's disease-type movements; such body movements can become permanent even after treatment has ceased.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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ChEBI Ontology
Outgoing reserpine (CHEBI:28487) has functional parent reserpic acid (CHEBI:46690)
reserpine (CHEBI:28487) has role adrenergic uptake inhibitor (CHEBI:35640)
reserpine (CHEBI:28487) has role antihypertensive agent (CHEBI:35674)
reserpine (CHEBI:28487) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
reserpine (CHEBI:28487) has role environmental contaminant (CHEBI:78298)
reserpine (CHEBI:28487) has role first generation antipsychotic (CHEBI:65190)
reserpine (CHEBI:28487) has role plant metabolite (CHEBI:76924)
reserpine (CHEBI:28487) has role xenobiotic (CHEBI:35703)
reserpine (CHEBI:28487) is a alkaloid ester (CHEBI:38481)
reserpine (CHEBI:28487) is a yohimban alkaloid (CHEBI:27358)
IUPAC Name
methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
Synonyms Sources
(−)-reserpine ChemIDplus
(3β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester NIST Chemistry WebBook
3,4,5-trimethoxybenzoyl methyl reserpate ChemIDplus
Apoplon ChemIDplus
Reserpin NIST Chemistry WebBook
Reserpine KEGG COMPOUND
Serpalan NIST Chemistry WebBook
Database Links Databases
2370 DrugCentral
C00001763 KNApSAcK
C06539 KEGG COMPOUND
D00197 KEGG DRUG
DB00206 DrugBank
HMDB0014351 HMDB
LSM-4162 LINCS
Reserpine Wikipedia
View more database links
Registry Numbers Types Sources
102014 Beilstein Registry Number Beilstein
102014 Reaxys Registry Number Reaxys
50-55-5 CAS Registry Number KEGG COMPOUND
50-55-5 CAS Registry Number NIST Chemistry WebBook
50-55-5 CAS Registry Number ChemIDplus
5326088 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
20701244 PubMed citation Europe PMC
20825390 PubMed citation Europe PMC
24603678 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag