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CHEBI:28077 - rifampicin
| Formula | C43H58N4O12 |
| Net Charge | 0 |
| Average Mass | 822.953 |
| Monoisotopic Mass | 822.40512 |
| SMILES | CO[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 |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| 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: | 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. Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. leprostatic drug A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions. DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA. 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). |
| Applications: | 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. leprostatic drug A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antiamoebic agent An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| rifampicin (CHEBI:28077) has role Escherichia coli metabolite (CHEBI:76971) |
| rifampicin (CHEBI:28077) has role analgesic (CHEBI:35480) |
| rifampicin (CHEBI:28077) has role angiogenesis inhibitor (CHEBI:48422) |
| rifampicin (CHEBI:28077) has role anti-HBV agent (CHEBI:64951) |
| rifampicin (CHEBI:28077) has role anti-HIV agent (CHEBI:64946) |
| rifampicin (CHEBI:28077) has role anti-ulcer drug (CHEBI:49201) |
| rifampicin (CHEBI:28077) has role antiamoebic agent (CHEBI:171664) |
| rifampicin (CHEBI:28077) has role antibacterial agent (CHEBI:33282) |
| rifampicin (CHEBI:28077) has role anticoagulant (CHEBI:50249) |
| rifampicin (CHEBI:28077) has role antiemetic (CHEBI:50919) |
| rifampicin (CHEBI:28077) has role antifibrotic agent (CHEBI:233423) |
| rifampicin (CHEBI:28077) has role antifungal agent (CHEBI:35718) |
| rifampicin (CHEBI:28077) has role antihypertensive agent (CHEBI:35674) |
| rifampicin (CHEBI:28077) has role antiinfective agent (CHEBI:35441) |
| rifampicin (CHEBI:28077) has role antimicrobial agent (CHEBI:33281) |
| rifampicin (CHEBI:28077) has role antineoplastic agent (CHEBI:35610) |
| rifampicin (CHEBI:28077) has role antiparkinson drug (CHEBI:48407) |
| rifampicin (CHEBI:28077) has role antirheumatic drug (CHEBI:35842) |
| rifampicin (CHEBI:28077) has role antitubercular agent (CHEBI:33231) |
| rifampicin (CHEBI:28077) has role antiviral agent (CHEBI:22587) |
| rifampicin (CHEBI:28077) has role cardiovascular drug (CHEBI:35554) |
| 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 hypoglycemic agent (CHEBI:35526) |
| rifampicin (CHEBI:28077) has role immunosuppressive agent (CHEBI:35705) |
| rifampicin (CHEBI:28077) has role laxative (CHEBI:50503) |
| 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) has role vasodilator agent (CHEBI:35620) |
| 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 naphthofuran (CHEBI:39270) |
| rifampicin (CHEBI:28077) is a organic molecular entity (CHEBI:50860) |
| 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 |
|---|---|
| rifampicin | KEGG DRUG |
| rifampicina | DrugBank |
| rifampicine | WHO MedNet |
| rifampicinum | DrugBank |
| Synonyms | Source |
|---|---|
| 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV | ChemIDplus |
| Abrifam | ChEMBL |
| BA 411661E | ChEMBL |
| BA 41166/E | ChEMBL |
| BA-41166/E | ChEMBL |
| BA-41166E | ChEMBL |
| Brand Names | Source |
|---|---|
| Eremfat | ChEMBL |
| Rifa | ChEMBL |
| Rifampin component of rifamate | ChEMBL |
| Rifampin component of rifater | ChEMBL |
| Rimactane | ChEMBL |
| Manual Xrefs | Databases |
|---|---|
| C06688 | KEGG COMPOUND |
| D00211 | KEGG DRUG |
| DB01045 | DrugBank |
| HMDB0015179 | HMDB |
| NL6509961 | Patent |
| RFP | PDBeChem |
| Rifampicin | Wikipedia |
| US3342810 | Patent |
| Registry Numbers | Sources |
|---|---|
| Reaxys:5723476 | Reaxys |
| CAS:13292-46-1 | ChemIDplus |
| CAS:13292-46-1 | KEGG COMPOUND |
| Citations |
|---|