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

General Information of Drug (ID: DR0026)
Drug Name
Phenanthrenequinone
Synonyms
Phenanthraquinone; Phenanthrene-9,10-dione; 9,10-Phenanthrenequinone; YYVYAPXYZVYDHN-UHFFFAOYSA-N; phenanthrene-9,10-quinone; 42L7BZ8H74; 9,10-PHENANTHRENEDIONE; 9,10-Phenanthraquinone; 9,10-Phenanthroquinone; 9,10-dihydrophenanthrene-9,10-dione; 9-10 Phenanthrene quinone; AI3-23739; AK-96664; BRN 0608838; CCRIS 7615; CHEBI:37454; CHEMBL51931; EINECS 201-515-5; HSDB 4489; MFCD00001163; MLS000571180; MLS000881132; NSC 10446; Phenanthrene, 9,10-dihydro-9,10-dioxo-; SMR000150826; UNII-42L7BZ8H74
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 208.21 Topological Polar Surface Area 34.1
Heavy Atom Count 16 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
6763
ChEBI ID
CHEBI:37454
CAS Number
84-11-7
TTD Drug ID
D0Q2YJ
Formula
C14H8O2
Canonical SMILES
C1=CC=C2C(=C1)C3=CC=CC=C3C(=O)C2=O
InChI
1S/C14H8O2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8H
InChIKey
YYVYAPXYZVYDHN-UHFFFAOYSA-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
9,10-Phenanthrene hydroquinone DM004089 N. A. Reduction - Reduction 1 [2] , [4]
Phenanthrenequinone Metabolite D1 DM004084 N. A. Unclear 1 [2]
O-mono-glucuronosyl catechol DM004091 N. A. Unclear 2 [2]
O-mono-methyl catechol DM004092 N. A. Unclear 2 [2]
O-mono-methyl-O-mono-sulfonated catechol DM004093 N. A. Unclear 2 [2]
O-mono-sulfonated catechol DM004090 N. A. Unclear 2 [2]
Phenanthrenequinone Metabolite D2 DM004085 N. A. Unclear 2 [2]
Phenanthrenequinone Metabolite D4 DM004087 N. A. Unclear 2 [2]
Phenanthrenequinone Metabolite D3 DM004086 N. A. Unclear 3 [2]
Phenanthrenequinone Metabolite D5 DM004088 N. A. Unclear 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004460 Phenanthrenequinone Phenanthrenequinone Metabolite D1 Unclear Unclear [2]
MR004465 Phenanthrenequinone 9,10-Phenanthrene hydroquinone Reduction - Reduction NQO1 [2], [4]
MR004466 9,10-Phenanthrene hydroquinone O-mono-sulfonated catechol Unclear SULT1A1 [2]
MR004467 9,10-Phenanthrene hydroquinone O-mono-glucuronosyl catechol Unclear UGT1A1 [2]
MR004468 9,10-Phenanthrene hydroquinone O-mono-methyl catechol Unclear COMT [2]
MR004469 9,10-Phenanthrene hydroquinone O-mono-methyl-O-mono-sulfonated catechol Unclear COMT ... [2]
MR004461 Phenanthrenequinone Metabolite D1 Phenanthrenequinone Metabolite D2 Unclear Unclear [2]
MR004463 Phenanthrenequinone Metabolite D1 Phenanthrenequinone Metabolite D4 Unclear Unclear [2]
MR004462 Phenanthrenequinone Metabolite D2 Phenanthrenequinone Metabolite D3 Unclear SULT1A1 [2]
MR004464 Phenanthrenequinone Metabolite D4 Phenanthrenequinone Metabolite D5 Unclear SULT1A1 [2]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[2]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[3]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Homo sapiens
CBR3_HUMAN
1.1.1.184
[3]
Quinone reductase 1 (NQO1) DME0097 Homo sapiens
NQO1_HUMAN
1.6.5.2
[2] , [4]
Small intestine reductase (AKR1B10) DME0398 Homo sapiens
AK1BA_HUMAN
1.1.1.21
[5]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
⏷ Show the Full List of 7  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Km = 0.0354 microM
CBR1_HUMAN
[3]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Km = 0.0043 microM
CBR3_HUMAN
[6]
References
1 Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. J Med Chem. 2007 Nov 15;50(23):5727-34.
2 Metabolism of a representative oxygenated polycyclic aromatic hydrocarbon (PAH) phenanthrene-9,10-quinone in human hepatoma (HepG2) cells
3 Studies on reduction of S-nitrosoglutathione by human carbonyl reductases 1 and 3. Chem Biol Interact. 2011 May 30;191(1-3):95-103.
4 Cytotoxicity of Air Pollutant 9,10-Phenanthrenequinone: Role of Reactive Oxygen Species and Redox Signaling
5 Exposure to 9,10-phenanthrenequinone accelerates malignant progression of lung cancer cells through up-regulation of aldo-keto reductase 1B10. Toxicol Appl Pharmacol. 2014 Jul 15;278(2):180-9.
6 Analysis of the substrate-binding site of human carbonyl reductases CBR1 and CBR3 by site-directed mutagenesis. Chem Biol Interact. 2009 Mar 16;178(1-3):234-41.

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