Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMT3QYZ)

• Drug Name: Acenaphthenol Drug Info
• Synonyms: GEO-00001; MXUCIEHYJYRTLT-UHFFFAOYSA-; MXUCIEHYJYRTLT-UHFFFAOYSA-N; SCHEMBL345448; W-200056; 1,2-Dihydro-1-acenaphthylenol; 1,2-dihydroacenaphthylen-1-ol; 1-ACENAPHTHENOL; 1-Acenaphthalenol; 1-Acenaphthenol, 99%; 1-Acenaphthylenol, 1,2-dihydro-; 1-Acenaphthylenol,1,2-dihydro-; 1-Acenaphthylenol,2-dihydro-; 1-Hydroxyacenaphthene; 28807-94-5; 7-Acenaphthenol; AC1L2L0C; AC1Q7A0H; ACMC-1B4IN; Acenaphthen-1-ol; Acenaphthene-1-ol; 1-Acenaphthenol; Acenaphthenol-1; Acenaphthylenol, 1,2-dihydro-; DTXSID20951449; HMS1666F13
• Cross-matching ID:
  PubChem CID: 22750
  CAS Number: CAS 6306-07-6
  TTD Drug ID: DMT3QYZ
  INTEDE Drug ID: DR2000

Molecule-Related Drug Atlas

Drug(s) Metabolized By Aldo-keto reductase 1C3 (AKR1C3)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Doxorubicin	DMVP5YE	Acute myelogenous leukaemia	2A41	Approved	[5]
FENOFIBRIC ACID	DMGO2MC	Cardiovascular disease	BA00-BE2Z	Approved	[6]
ANDROSTERONE	DMITJAK	N. A.	N. A.	Phase 3	[1]
Trastuzumab emtansine	DMU1LXS	HER2-positive breast cancer	2C60-2C65	Phase 2	[7]
4-oxo-nonenal	DMPX1J9	Discovery agent	N.A.	Investigative	[8]
Indan-1-ol	DMMLQZJ	N. A.	N. A.	Investigative	[1]

Drug(s) Affected By Aldo-keto reductase family 1 member C3 (AKR1C3)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Doxorubicin	DMVP5YE	Acute myelogenous leukaemia	2A41	Approved	[9]
Meclofenamic acid	DM05FXR	Ankylosing spondylitis	FA92.0	Approved	[10]
Diazepam	DM08E9O	Alcohol withdrawal		Approved	[11]
Levonorgestrel	DM1DP7T	Atypical endometrial hyperplasia		Approved	[12]
Desogestrel	DM27U4Y	Contraception	QA21	Approved	[12]
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[10]
Sulindac	DM2QHZU	Acute myelogenous leukaemia	2A41	Approved	[10]
Simvastatin	DM30SGU	Arteriosclerosis	BD40	Approved	[13]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[14]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[15]

Drug(s) Affected By Aldo-keto reductase family 1 member C2 (AKR1C2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Meclofenamic acid	DM05FXR	Ankylosing spondylitis	FA92.0	Approved	[10]
Diazepam	DM08E9O	Alcohol withdrawal		Approved	[11]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[16]
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[17]
Sulindac	DM2QHZU	Acute myelogenous leukaemia	2A41	Approved	[10]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[18]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[19]
Aspirin	DM672AH	Acute coronary syndrome	BA41	Approved	[10]
Liothyronine	DM6IR3P	Congenital hypothyroidism		Approved	[20]
Testosterone	DM7HUNW	Hot flushes	GA30	Approved	[21]

Drug(s) Affected By Aldo-keto reductase family 1 member C1 (AKR1C1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[22]
Meclofenamic acid	DM05FXR	Ankylosing spondylitis	FA92.0	Approved	[10]
Diazepam	DM08E9O	Alcohol withdrawal		Approved	[11]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[23]
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[10]
Sulindac	DM2QHZU	Acute myelogenous leukaemia	2A41	Approved	[10]
Simvastatin	DM30SGU	Arteriosclerosis	BD40	Approved	[24]
Glimepiride	DM5FSJA	Diabetic complication	5A2Y	Approved	[25]
Ethacrynic acid	DM60QMR	Edema	MG29	Approved	[23]
Aspirin	DM672AH	Acute coronary syndrome	BA41	Approved	[10]

Drug(s) Affected By Cytochrome P450 2A13 (CYP2A13)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[26]
Rifampicin	DM5DSFZ	Non-insulin dependent diabetes	5A11	Approved	[27]
Phenobarbital	DMXZOCG	Cluster headache	8A81.0	Approved	[27]
Amodiaquine	DME4RA8	Malaria	1F40-1F45	Approved	[28]
Benzo(a)pyrene	DMN7J43	N. A.	N. A.	Phase 1	[29]
HELENALIN	DMMCI4H	N. A.	N. A.	Terminated	[30]
COUMARIN	DM0N8ZM	Discovery agent	N.A.	Investigative	[31]
BRN-3548355	DM4KXT0	N. A.	N. A.	Investigative	[31]
Chrysin	DM7V2LG	Discovery agent	N.A.	Investigative	[32]
9-phenanthrol	DMJFBQ1	Discovery agent	N.A.	Investigative	[33]

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Aldo-keto reductase 1C3 (AKR1C3) Main DME	DEGQTXO	AK1C3_HUMAN	Substrate	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Regulation of Drug Effects	[2]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Biotransformations	[3]
Aldo-keto reductase family 1 member C3 (AKR1C3)	OTU2SXBA	AK1C3_HUMAN	Biotransformations	[3]
Cytochrome P450 2A13 (CYP2A13)	OTVUDLT3	CP2AD_HUMAN	Biotransformations	[4]

References

• [1] Expression and characterization of four recombinant human dihydrodiol dehydrogenase isoforms: oxidation of trans-7, 8-dihydroxy-7,8-dihydrobenzo[a]pyrene to the activated o-quinone metabolite benzo[a]pyrene-7,8-dione. Biochemistry. 1998 May 12;37(19):6781-90.
• [2] Derivatives of pyrimidine, phthalimide and anthranilic acid as inhibitors of human hydroxysteroid dehydrogenase AKR1C1. Chem Biol Interact. 2009 Mar 16;178(1-3):158-64.
• [3] New enzymatic assay for the AKR1C enzymes. Chem Biol Interact. 2013 Feb 25;202(1-3):204-9.
• [4] Oxidation of Acenaphthene and Acenaphthylene by Human Cytochrome P450 Enzymes. Chem Res Toxicol. 2015 Feb 16;28(2):268-78.
• [5] Inactivation of the anticancer drugs doxorubicin and oracin by aldo-keto reductase (AKR) 1C3. Toxicol Lett. 2008 Sep;181(1):1-6.
• [6] In vitro metabolism of fenofibric acid by carbonyl reducing enzymes. Chem Biol Interact. 2016 Oct 25;258:153-8.
• [7] The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7.
• [8] Instability of C154Y variant of aldo-keto reductase 1C3. Chem Biol Interact. 2017 Oct 1;276:194-202.
• [9] Bringing in vitro analysis closer to in vivo: studying doxorubicin toxicity and associated mechanisms in 3D human microtissues with PBPK-based dose modelling. Toxicol Lett. 2018 Sep 15;294:184-192.
• [10] Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs. Chem Biol Interact. 2009 Mar 16;178(1-3):221-7.
• [11] Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5.
• [12] Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3. Chem Biol Interact. 2011 May 30;191(1-3):227-33.
• [13] In-vivo effects of simvastatin and rosuvastatin on global gene expression in peripheral blood leucocytes in a human inflammation model. Pharmacogenet Genomics. 2008 Feb;18(2):109-20.
• [14] AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids. Chem Biol Interact. 2009 Mar 16;178(1-3):138-44.
• [15] Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
• [16] Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells. Cancer Res. 2002 Nov 1;62(21):6246-54.
• [17] A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. Cutan Ocul Toxicol. 2010 Sep;29(3):171-92.
• [18] Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
• [19] Aberrantly expressed genes in HaCaT keratinocytes chronically exposed to arsenic trioxide. Biomark Insights. 2011 Feb 8;6:7-16.
• [20] Thyroid hormone responsive genes in cultured human fibroblasts. J Clin Endocrinol Metab. 2005 Feb;90(2):936-43.
• [21] The exosome-like vesicles derived from androgen exposed-prostate stromal cells promote epithelial cells proliferation and epithelial-mesenchymal transition. Toxicol Appl Pharmacol. 2021 Jan 15;411:115384. doi: 10.1016/j.taap.2020.115384. Epub 2020 Dec 25.
• [22] Progestin effects on expression of AKR1C1-AKR1C3, SRD5A1 and PGR in the Z-12 endometriotic epithelial cell line. Chem Biol Interact. 2013 Feb 25;202(1-3):218-25.
• [23] Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res. 1999 Feb 1;59(3):607-14.
• [24] Simvastatin inactivates beta1-integrin and extracellular signal-related kinase signaling and inhibits cell proliferation in head and neck squamous cell carcinoma cells. Cancer Sci. 2007 Jun;98(6):890-9.
• [25] Initro inhibition of AKR1Cs by sulphonylureas and the structural basis. Chem Biol Interact. 2015 Oct 5;240:310-5.
• [26] CYP1A1/1B1 and CYP2A6/2A13 activity is conserved in cultures of differentiated primary human tracheobronchial epithelial cells. Toxicol In Vitro. 2011 Jun;25(4):922-9.
• [27] Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins. Cell Biol Toxicol. 2012 Apr;28(2):69-87.
• [28] Apoptosis contributes to the cytotoxicity induced by amodiaquine and its major metabolite N-desethylamodiaquine in hepatic cells. Toxicol In Vitro. 2020 Feb;62:104669. doi: 10.1016/j.tiv.2019.104669. Epub 2019 Oct 16.
• [29] Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
• [30] In vitro metabolism of helenalin and its inhibitory effect on human cytochrome P450 activity. Arch Toxicol. 2022 Mar;96(3):793-808. doi: 10.1007/s00204-021-03218-6. Epub 2022 Jan 6.
• [31] Functional characterization of CYP2A13 polymorphisms. Xenobiotica. 2007 Dec;37(12):1439-49. doi: 10.1080/00498250701666265.
• [32] Oxidation of Flavone, 5-Hydroxyflavone, and 5,7-Dihydroxyflavone to Mono-, Di-, and Tri-Hydroxyflavones by Human Cytochrome P450 Enzymes. Chem Res Toxicol. 2019 Jun 17;32(6):1268-1280. doi: 10.1021/acs.chemrestox.9b00078. Epub 2019 Apr 17.
• [33] Structure-Function Studies of Naphthalene, Phenanthrene, Biphenyl, and Their Derivatives in Interaction with and Oxidation by Cytochromes P450 2A13 and 2A6. Chem Res Toxicol. 2016 Jun 20;29(6):1029-40. doi: 10.1021/acs.chemrestox.6b00083. Epub 2016 May 12.