Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1568)
Drug Name
Tetracycline
Synonyms
Tetrabon; Tetraciclina; Tetracycl; Tetracyclin; Tetracycline base; Tetracyclinum; Tetracyn; Tetradecin; Tetrafil; Tetraverine; Tetrazyklin; Topicycline; Tsiklomistsin; Tsiklomitsin; Vetacyclinum; tetracycline; 60-54-8; Abramycin; Achromycin; Achromycin V; Agromicina; Ambramicina; Ambramycin; Cefracycline; Criseociclina; Cyclopar; Democracin; Deschlorobiomycin; Hostacyclin; Lexacycline; Limecycline; Mericycline; Micycline; Neocycline; Omegamycin; Orlycycline; Panmycin; Polycycline; Polyotic; Purocyclina; Roviciclina; Solvocin; Sumycin; Abricycline
Indication Spotted fever [ICD11: 1C31] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 444.4 Topological Polar Surface Area 182
Heavy Atom Count 32 Rotatable Bond Count 2
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
54675776
PubChem SID
8799 ; 597088 ; 855950 ; 7847269 ; 7980765 ; 8144439 ; 11336002 ; 11361241 ; 11363928 ; 11366490 ; 11369052 ; 11371550 ; 11373922 ; 11377214 ; 11462213 ; 11466168 ; 11467288 ; 11485193 ; 11485895 ; 11489145 ; 11490381 ; 11492167 ; 11494848 ; 14759560 ; 14930699 ; 24888860 ; 24900120 ; 25643873 ; 36634859 ; 39289915 ; 39404343 ; 43135372 ; 46506693 ; 47216820 ; 47515360 ; 47662329 ; 47662330 ; 47810796 ; 48035170 ; 48035171 ; 48416604 ; 49698367 ; 53790074 ; 53790289 ; 56311360 ; 56311878 ; 56313073 ; 56313451 ; 56314320 ; 57288852
ChEBI ID
ChEBI:27902
CAS Number
60-54-8
TTD Drug ID
D0Z5PF
Formula
C22H24N2O8
Canonical SMILES
CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
InChI
1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChIKey
NWXMGUDVXFXRIG-WESIUVDSSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4-epianhydrotetracycline DM004582
54678401
Unclear 1 [7] , [7]
Glucosyl Tetracycline DM004581 N. A. Conjugation - Glucosylation forward reaction 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004912 Tetracycline Glucosyl Tetracycline Conjugation - Glucosylation forward reaction yjiC [4]
MR004913 Tetracycline 4-epianhydrotetracycline Unclear Unclear [7], [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Hydroxybenzoate 3-monooxygenase (pobA) DME1087 Pseudomonas aeruginosa
PHHY_PSEAE
1.14.13.2
[3]
Hydroxybenzoate 3-monooxygenase (pobA) DME1088 Pseudomonas fluorescens
PHHY_PSEFL
1.14.13.2
[3]
Hydroxybenzoate 3-monooxygenase (pobA) DME1089 Pseudomonas putida
Q88H28_PSEPK
1.14.13.2
[3]
NDP-glycosyltransferase YjiC (yjiC) DMEN241 Bacillus licheniformis
NDPGT_BACLD
2.4.1.384
[4]
Unclear metabolic mechanism (DME-unclear) DME1279 Methanobrevibacter oralis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1280 Methanobrevibacter smithii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1281 Methanomassiliicoccus luminyensis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1282 Methanosphaera stadtmanae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1450 Prevotella veroralis Not Available Not Available [6]
⏷ Show the Full List of 10  DME(s)
References
1 Tetracycline was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The In vitro hepatic metabolism of quinine in mice, rats and dogs: comparison with human liver microsomes. J Pharmacol Exp Ther. 1997 Dec;283(3):1168-76.
3 Structural comparison of p-hydroxybenzoate hydroxylase (PobA) from Pseudomonas putida with PobA from other Pseudomonas spp. and other monooxygenases. Acta Crystallogr F Struct Biol Commun. 2019 Jul 1;75(Pt 7):507-514.
4 Bioconversion of Tetracycline Antibiotics to Novel Glucoside Derivatives by Single-Vessel Multienzymatic Glycosylation
5 The antimicrobial resistance pattern of cultured human methanogens reflects the unique phylogenetic position of archaea. J Antimicrob Chemother. 2011 Sep;66(9):2038-44.
6 The tet(Q) gene in bacteria isolated from patients with refractory periodontal disease. Oral Microbiol Immunol. 1994 Aug;9(4):251-5.
7 Toxicity of single and combined 4-epianhydrotetracycline and cadmium at environmentally relevant concentrations on the zebrafish embryos (Danio rerio)

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