CHEBI:133011 - oxytetracycline zwitterion

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ChEBI Name oxytetracycline zwitterion
ChEBI ID CHEBI:133011
Definition A zwitterion obtained by transfer of a proton from the 2-hydroxy group to the adjacent tertiary amino group of oxytetracycline; major species at pH 7.3.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C22H24N2O9
Net Charge 0
Average Mass 460.435
Monoisotopic Mass 460.14818
InChI InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
InChIKey IWVCMVBTMGNXQD-PXOLEDIWSA-N
SMILES [C@@]12([C@](C(=C3C(C=4C(=CC=CC4[C@@]([C@]3([C@@H]1O)[H])(C)O)O)=O)O)(C(C(C(N)=O)=C([C@H]2[NH+](C)C)[O-])=O)O)[H]
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via tetracyclines )
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ChEBI Ontology
Outgoing oxytetracycline zwitterion (CHEBI:133011) is a a tetracycline zwittterion (CHEBI:144644)
oxytetracycline zwitterion (CHEBI:133011) is a zwitterion (CHEBI:27369)
oxytetracycline zwitterion (CHEBI:133011) is tautomer of oxytetracycline (CHEBI:27701)
Incoming oxytetracycline (CHEBI:27701) is tautomer of oxytetracycline zwitterion (CHEBI:133011)
IUPAC Name
(1S,4aS,11S,11aR,12S,12aR)-3-carbamoyl-1-(dimethylazaniumyl)-4a,5,7,11,12-pentahydroxy-11-methyl-4,6-dioxo-1,4,4a,6,11,11a,12,12a-octahydrotetracen-2-olate
Synonym Source
oxytetracycline UniProt
Manual Xref Database
CPD-19255 MetaCyc
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Last Modified
31 January 2017