rifampicin (CHEBI:28077)

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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

Supplier Information	ChemicalBook:CB4217972, ChemicalBook:CB7686195

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M END): 21 ms

reading 117 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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117 atoms created

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Wikipedia	License
Hydrogen is a chemical element; it has the symbol H and atomic number 1. It is the lightest and most abundant chemical element in the universe, constituting about 75% of all normal matter. Stars, including the Sun, mainly consist of hydrogen in a plasma state, while on Earth, hydrogen is found in water and organic compounds as the gas H2 (dihydrogen), and in other molecular forms. The most common isotope of hydrogen (1H) consists of one proton, one electron, and no neutrons. Under standard conditions, hydrogen is a gas of diatomic molecules with the formula H2, called dihydrogen, or sometimes hydrogen gas, molecular hydrogen, or simply hydrogen. Dihydrogen is colorless, odorless, non-toxic, and highly combustible. Hydrogen gas was first produced artificially in the 17th century by the reaction of acids with metals. Henry Cavendish, in 1766–1781, identified hydrogen gas as a distinct substance and discovered its property of producing water when burned; hence its name means 'water-former' in Greek. Understanding the colors of light absorbed and emitted by hydrogen was a crucial part of developing quantum mechanics. Hydrogen, typically nonmetallic except under extreme pressure, readily forms covalent bonds with most nonmetals, contributing to the formation of compounds like water and various organic substances. Its role is crucial in acid-base reactions, which mainly involve proton exchange among soluble molecules. In ionic compounds, hydrogen can take the form of either a negatively charged anion, where it is known as hydride, or as a positively charged cation, H+, called a proton. Although tightly bonded to water molecules, protons strongly affect the behavior of aqueous solutions, as reflected in the importance of pH. Hydride, on the other hand, is rarely observed because it tends to deprotonate solvents, yielding H2. In the early universe, neutral hydrogen atoms formed about 370,000 years after the Big Bang as the universe expanded and plasma had cooled enough for electrons to remain bound to protons. Once stars formed most of the atoms in the intergalactic medium re-ionized. Nearly all hydrogen production is done by transforming fossil fuels, particularly steam reforming of natural gas. It can also be produced from electricity by electrolysis, however this process is more expensive. Its main industrial uses include fossil fuel processing and ammonia production for fertilizer. Emerging uses for hydrogen include the use of fuel cells to generate electricity.
Read full article at Wikipedia

Formula

C43H58N4O12

Net Charge

Average Mass

822.94020

Monoisotopic Mass

822.40512

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:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

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. antiamoebic agent An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae. 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. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

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 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	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[23.3.1.1^4,7.0^5,28]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

Manual Xrefs	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	Reaxys Registry Number	Reaxys

Citations

Last Modified

28 October 2021

CHEBI:28077 - rifampicin

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