CHEBI:28077 - rifampicin

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ChEBI Name rifampicin
ChEBI ID CHEBI:28077
Definition A member of the class of rifamycins that is a a semisynthetic antibiotic derived from Amycolatopsis rifamycinica (previously known as Amycolatopsis mediterranei and Streptomyces mediterranei)
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45308, CHEBI:8858, CHEBI:26577
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Formula C43H58N4O12
Net Charge 0
Average Mass 822.94020
Monoisotopic Mass 822.405
InChI InChI=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
InChIKey JQXXHWHPUNPDRT-WLSIYKJHSA-N
SMILES CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(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)c(\C=N\N1CCN(C)CC1)c(O)c4c3C2=O
Metabolite of Species Details
Escherichia coli (NCBI:562) See: PubMed
Roles Classification
Biological Role(s): 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).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
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.
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.
pregnane X receptor agonist
An agonist that selectively binds to and activates a pregnane X receptor.
Application(s): leprostatic drug
A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions.
antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rifampicin (CHEBI:28077) has role Escherichia coli metabolite (CHEBI:76971)
rifampicin (CHEBI:28077) has role angiogenesis inhibitor (CHEBI:48422)
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 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 2'-hydroxyrifampicin (CHEBI:111544) 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 Sources
rifampicin KEGG DRUG
rifampicina DrugBank
rifampicinum DrugBank
Synonyms Sources
3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV ChemIDplus
RFP DrugBank
rifamcin ChEBI
Rifampicin KEGG COMPOUND
Rifampin KEGG COMPOUND
Database Links Databases
C06688 KEGG COMPOUND
D00211 KEGG DRUG
DB01045 DrugBank
HMDB0015179 HMDB
NL6509961 Patent
RFP PDBeChem
Rifampicin Wikipedia
US3342810 Patent
View more database links
Registry Numbers Types Sources
13292-46-1 CAS Registry Number KEGG COMPOUND
13292-46-1 CAS Registry Number ChemIDplus
5723476 Beilstein Registry Number Beilstein
5723476 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
27 March 2017