CHEBI:71365 - rifampicin zwitterion

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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; major species at pH 7.3.
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 822.40512
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\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)
O-(ADP-D-ribosyl)-rifampicin(2−) (CHEBI:142707) has functional parent rifampicin zwitterion (CHEBI:71365)
rifampicin ortho-naphthoquinone carboxamide(2−) (CHEBI:142730) has functional parent rifampicin zwitterion (CHEBI:71365)
rifampicin para-naphthoquinone carboxamide(2−) (CHEBI:142731) has functional parent rifampicin zwitterion (CHEBI:71365)
rifampicin hemiaminal(2−) (CHEBI:142729) 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
11 June 2024