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CHEBI:28077 - rifampicin

Default Structure
ChEBI IDCHEBI:28077
ChEBI Namerifampicin
Stars
DefinitionA member of the class of rifamycins that is a a semisynthetic antibiotic derived from Amycolatopsis rifamycinica (previously known as Amycolatopsis mediterranei and Streptomyces mediterranei).
Secondary ChEBI IDsCHEBI:8858, CHEBI:26577, CHEBI:45308
Last Modified28 October 2021
DownloadsMolfile
FormulaC43H58N4O12
Net Charge0
Average Mass822.953
Monoisotopic Mass822.40512
SMILESCO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c(/C=N/N5CCN(C)CC5)c(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C
InChIInChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1
InChIKeyJQXXHWHPUNPDRT-WLSIYKJHSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
leprostatic drug  A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions.
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
pregnane X receptor agonist  An agonist that selectively binds to and activates a pregnane X receptor.
EC 2.7.7.6 (RNA polymerase) inhibitor  An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6).
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
Applications:
leprostatic drug  A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions.
antiamoebic agent  An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
rifampicin (CHEBI:28077) has role Escherichia coli metabolite (CHEBI:76971)
rifampicin (CHEBI:28077) has role angiogenesis inhibitor (CHEBI:48422)
rifampicin (CHEBI:28077) has role antiamoebic agent (CHEBI:171664)
rifampicin (CHEBI:28077) has role antineoplastic agent (CHEBI:35610)
rifampicin (CHEBI:28077) has role antitubercular agent (CHEBI:33231)
rifampicin (CHEBI:28077) has role DNA synthesis inhibitor (CHEBI:59517)
rifampicin (CHEBI:28077) has role EC 2.7.7.6 (RNA polymerase) inhibitor (CHEBI:37416)
rifampicin (CHEBI:28077) has role geroprotector (CHEBI:176497)
rifampicin (CHEBI:28077) has role leprostatic drug (CHEBI:35816)
rifampicin (CHEBI:28077) has role neuroprotective agent (CHEBI:63726)
rifampicin (CHEBI:28077) has role pregnane X receptor agonist (CHEBI:77318)
rifampicin (CHEBI:28077) has role protein synthesis inhibitor (CHEBI:48001)
rifampicin (CHEBI:28077) is a N-iminopiperazine (CHEBI:46847)
rifampicin (CHEBI:28077) is a N-methylpiperazine (CHEBI:46920)
rifampicin (CHEBI:28077) is a cyclic ketal (CHEBI:59779)
rifampicin (CHEBI:28077) is a hydrazone (CHEBI:38532)
rifampicin (CHEBI:28077) is a rifamycins (CHEBI:26580)
rifampicin (CHEBI:28077) is a semisynthetic derivative (CHEBI:72588)
rifampicin (CHEBI:28077) is tautomer of rifampicin zwitterion (CHEBI:71365)
Incoming Relation(s)
2'-hydroxyrifampicin (CHEBI:111544) has functional parent rifampicin (CHEBI:28077)
21-phosphorifampicin (CHEBI:140276) has functional parent rifampicin (CHEBI:28077)
rifampicin zwitterion (CHEBI:71365) is tautomer of rifampicin (CHEBI:28077)
IUPAC Name 
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),1(29),2,4,9,19,21,25,27-nonaen-13-yl acetate
INNs  Source
rifampicinKEGG DRUG
rifampicinaDrugBank
rifampicinumDrugBank
Synonyms  Source
3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SVChemIDplus
RFPDrugBank
rifamcinChEBI
RifampicinKEGG COMPOUND
RifampinKEGG COMPOUND
Manual XrefsDatabases
C06688KEGG COMPOUND
D00211KEGG DRUG
DB01045DrugBank
HMDB0015179HMDB
NL6509961Patent
RFPPDBeChem
RifampicinWikipedia
US3342810Patent
Registry NumbersSources
Reaxys:5723476Reaxys
CAS:13292-46-1KEGG COMPOUND
CAS:13292-46-1ChemIDplus
Citations