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

General Information of Drug (ID: DR0046)
Drug Name
Adenosine
Synonyms
Adenine nucleoside; Adenine riboside; Adenocard; Adenocor; Adenoscan; Adenosin; Adenosin [German]; Adenosine [USAN:BAN]; Boniton; Caswell No. 010B; Myocol; Nucleocardyl; Pallacor; Sandesin; USAF CB-10; adenosine; beta-Adenosine; beta-D-Adenosine; beta-D-Ribofuranoside, adenine-9; 58-61-7; 6-Amino-9-beta-D-ribofuranosyl-9H-purine; 6-Amino-9beta-D-ribofuranosyl-9H-purine; 9-beta-D-Ribofuranosidoadenine; 9-beta-D-Ribofuranosyl-9H-purin-6-amine; 9-beta-D-Ribofuranosyladenine; 9beta-D-Ribofuranosyladenine; Ade-Rib
Indication Atrial fibrillation [ICD11: BC81] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 267.24 Topological Polar Surface Area 140
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
60961
PubChem SID
2103 ; 3512 ; 584484 ; 584490 ; 585862 ; 586357 ; 597013 ; 819854 ; 821994 ; 823447 ; 825728 ; 826920 ; 828107 ; 828519 ; 829493 ; 830178 ; 830391 ; 833174 ; 833907 ; 836875 ; 837192 ; 855078 ; 855932 ; 3136392 ; 7847113 ; 7885717 ; 7978645 ; 8023217 ; 8024149 ; 8027268 ; 8143428 ; 8187141 ; 10318629 ; 11110168 ; 11120317 ; 11120805 ; 11121293 ; 11371396 ; 11484930 ; 11489073 ; 11490104 ; 11532406 ; 11532673 ; 11537606 ; 12090919 ; 14716094 ; 14774851 ; 14799162 ; 22394812 ; 24277685
ChEBI ID
ChEBI:16335
CAS Number
58-61-7
TTD Drug ID
D06IAR
Formula
C10H13N5O4
Canonical SMILES
C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
InChI
1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChIKey
OIRDTQYFTABQOQ-KQYNXXCUSA-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
Adenosine Phosphate DM000018
6083
Other reaction - Phosphorylation 1 [2] , [5]
Inosine DM003100
135398641
Oxidation - Deamination 1 [4] , [5]
Adenosine diphosphate DM000019
6022
Other reaction - Phosphorylation 2 [2] , [5]
Naproxen metabolite M1 DM003064
135398638
Other reaction - Phosphorylation 2 [2] , [5]
Adenosine Phosphate DM000018
6083
Other reaction - Dephosphorylation 3 [2] , [5]
ATP DM000020
5957
Other reaction - Phosphorylation 3 [2] , [5]
Xanthine DM003088
1188
Oxidation - Oxidation 3 [2] , [5]
Adenosine DM003051
60961
Other reaction - Dephosphorylation 4 [2] , [5]
Adenosine diphosphate DM000019
6022
Other reaction - Dephosphorylation 4 [2] , [5]
Adenosine Phosphate DM000018
6083
Other reaction - Dephosphorylation 4 [2] , [5]
Uric acid DM000021
1175
Oxidation - Oxidation 4 [2] , [5]
Adenosine DM003051
60961
Other reaction - Dephosphorylation 5 [2] , [5]
Adenosine Phosphate DM000018
6083
Other reaction - Dephosphorylation 5 [2] , [5]
Adenosine DM003051
60961
Other reaction - Dephosphorylation 6 [2] , [5]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000076 Adenosine AMP Other reaction - Phosphorylation ADK [2], [5]
MR000077 Adenosine Inosine Oxidation - Deamination ADA [4], [5]
MR000070 AMP ADP Other reaction - Phosphorylation AK1 [2], [5]
MR000078 Inosine Hypoxanthine Other reaction - Phosphorylation PNP [2], [5]
MR000073 ADP ATP Other reaction - Phosphorylation NME1 [2], [5]
MR000080 Hypoxanthine Xanthine Oxidation - Oxidation XDH [2], [5]
MR000074 ATP AMP Other reaction - Dephosphorylation Unclear [2], [5]
MR000075 ATP ADP Other reaction - Dephosphorylation ENTPD1 [2], [5]
MR000079 Xanthine Uric acid Oxidation - Oxidation XDH [2], [5]
MR000072 ADP AMP Other reaction - Dephosphorylation ENTPD1 [2], [5]
MR000071 AMP Adenosine Other reaction - Dephosphorylation NT5E [2], [5]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Adenosine aminohydrolase (ADA) DME0060 Homo sapiens
ADA_HUMAN
3.5.4.4
[2]
Adenosine kinase (ADK) DME0448 Homo sapiens
ADK_HUMAN
2.7.1.20
[2]
Adenylate kinase isoenzyme 1 (AK1) DMEN001 Homo sapiens
KAD1_HUMAN
3.6.1.5
[2]
Ecto-5'-nucleotidase (NT5E) DME0111 Homo sapiens
5NTD_HUMAN
3.1.3.5
[2]
Ectonucleoside triphosphate diphosphohydrolase 1 (ENTPD1) DMEN003 Homo sapiens
ENTP1_HUMAN
1.8.1.4
[2]
Nucleoside diphosphate kinase A (NME1) DMEN002 Homo sapiens
NDKA_HUMAN
2.7.1.30
[2]
Purine nucleoside phosphorylase (PNP) DME0437 Homo sapiens
PNPH_HUMAN
2.4.2.1
[2]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[3]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[4]
⏷ Show the Full List of 9  DME(s)
References
1 Adenosine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Adenosine Metabolism: Emerging Concepts for Cancer Therapy Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007.
3 Regulation of sulfate assimilation in plants: 7. Cysteine inactivation of adenosine 5'-phosphosulfate sulfotransferase in Lemna minor L. Plant Physiol. 1978 Mar;61(3):342-7.
4 DrugBank(Pharmacology-Metabolism)Adenosine
5 Purine signaling pathway dysfunction in autism spectrum disorders: Evidence from multiple omics data. Front Mol Neurosci. 2023 Feb 3;16:1089871. doi: 10.3389/fnmol.2023.1089871.

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