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

General Information of Drug (ID: DR0049)
Drug Name
Adriamycin
Synonyms
ADRIAMYCIN HYDROCHLORIDE; ADRIAMYCIN, HYDROCHLORIDE; Adriacin; Adriamycin PFS; Adriamycin RDF; Doxorubicin (Adriamycin) HCl; Doxorubicin (hydrochloride); Doxorubicin HCl; Doxorubicin Hydrochloride; Hydroxydaunorubicin hydrochloride; KW-125; Lipodox; 25316-40-9; 82F2G7BL4E; CAS-NOCAS_45111; CCRIS 740; CPD000058570; DSSTox_CID_10636; DSSTox_GSID_30636; DSSTox_GSID_45111; DSSTox_RID_78854; DSSTox_RID_80678; MLS001401460; NSC 123127; Rubex; SMR000058570; UNII-82F2G7BL4E
Indication Discovery agent Investigative [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 580 Topological Polar Surface Area 206
Heavy Atom Count 40 Rotatable Bond Count 5
Hydrogen Bond Donor Count 7 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
443939
PubChem SID
855944 ; 7848338 ; 7964547 ; 7964548 ; 7964549 ; 7964550 ; 7964551 ; 10299430 ; 10321288 ; 10321987 ; 11110522 ; 11110525 ; 11110526 ; 14764476 ; 14788917 ; 17389199 ; 24868204 ; 24893465 ; 26719671 ; 36887087 ; 46386781 ; 48422781 ; 48424796 ; 49681823 ; 49718188 ; 50126368 ; 57404558 ; 57650234 ; 77622457 ; 81092799 ; 91696143 ; 92125422 ; 103913768 ; 104234257 ; 104253167 ; 104630990 ; 113234498 ; 118048474 ; 124658966 ; 124757082 ; 124766325 ; 125163886 ; 125299286 ; 127319639 ; 127319640 ; 127319641 ; 127319642 ; 127319643 ; 127319644 ; 127319645
ChEBI ID
ChEBI:28748
CAS Number
23214-92-8
TTD Drug ID
D0F4KU
Formula
C27H30ClNO11
Canonical SMILES
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.Cl
InChI
1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1
InChIKey
MWWSFMDVAYGXBV-RUELKSSGSA-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
7-deoxydaxorubicinol DM001715
45038813
Unclear 1 [2]
Doxorubicin aglycone DM001981
72401
Unclear 1 [2]
Doxorubicin-semiquinone DM001716
131769966
Unclear 1 [2]
Doxorubicinol DM001717
83970
Unclear 1 [2]
Doxirubicinol hydroxyaglycone DM001714
10476988
Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000093 Adriamycin Doxorubicinol deoxaglycone Unclear POR ... [2]
MR000094 Adriamycin Doxorubicin-semiquinone Unclear NOS3 ... [2]
MR000095 Adriamycin Doxorubicinol Unclear CBR1 ... [2]
MR000096 Adriamycin Doxorubicin aglycone Unclear Unclear [2]
MR000092 Doxorubicin aglycone Doxirubicinol hydroxyaglycone Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1A1 (AKR1A1) DME0098 Homo sapiens
AK1A1_HUMAN
1.1.1.2
[2]
Aldo-keto reductase 1C3 (AKR1C3) DME0118 Homo sapiens
AK1C3_HUMAN
1.1.1.357
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[3]
NADPH-cytochrome P450 reductase (CPR) DME0076 Homo sapiens
NCPR_HUMAN
1.6.2.4
[2]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[2]
Nitric oxide synthase brain (NOS1) DME0122 Homo sapiens
NOS1_HUMAN
1.14.13.39
[2]
Nitric oxide synthase endothelial (NOS3) DME0123 Homo sapiens
NOS3_HUMAN
1.14.13.39
[2]
Nitric oxide synthase inducible (NOS2) DME0124 Homo sapiens
NOS2_HUMAN
1.14.13.39
[2]
Quinone reductase 1 (NQO1) DME0097 Homo sapiens
NQO1_HUMAN
1.6.5.2
[2]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[2]
⏷ Show the Full List of 10  DME(s)
References
1 Interaction of adriamycin with DNA as studied by resonance Raman spectroscopy. Nucleic Acids Res. 1982 Jun 25;10(12):3803-16.
2 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.
3 Glutathione transferase P1 polymorphism in neuroblastoma studied by endonuclease restriction mapping. Clin Chem Lab Med. 2001 Sep;39(9):830-5.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.