CHEBI:71365 - rifampicin zwitterion

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ChEBI Name rifampicin zwitterion
ChEBI ID CHEBI:71365
Definition A zwitterion obtained by transfer of a proton from the 5-hydroxy group to the tertiary amino group of rifampicin.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Eugeni Belda
Supplier Information
Download Molfile XML SDF
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\N1CC[NH+](C)CC1)c(O)c4c3C2=O
ChEBI Ontology
Outgoing rifampicin zwitterion (CHEBI:71365) is a zwitterion (CHEBI:27369)
rifampicin zwitterion (CHEBI:71365) is tautomer of rifampicin (CHEBI:28077)
Incoming 21-phosphorifampicin(2−) (CHEBI:140195) has functional parent rifampicin zwitterion (CHEBI:71365)
rifampicin (CHEBI:28077) is tautomer of rifampicin zwitterion (CHEBI:71365)
IUPAC Name
(2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-21-acetoxy-6,9,17,19-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-{(E)-[(4-methylpiperazin-4-ium-1-yl)imino]methyl}-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-5-olate
Synonym Source
rifampicin UniProt
Last Modified
20 November 2014