Details of the Drug

General Information of Drug (ID: DMG8KS9)

Drug Name
Phenanthrene-9,10-dione
Synonyms
Phenanthrene-9,10-dione; 9,10-Phenanthrenequinone; 84-11-7; Phenanthrenequinone; 9,10-PHENANTHRENEDIONE; 9,10-Phenanthraquinone; Phenanthraquinone; 9,10-Phenanthroquinone; 9-10 Phenanthrene quinone; UNII-42L7BZ8H74; CCRIS 7615; Phenanthrene, 9,10-dihydro-9,10-dioxo-; HSDB 4489; EINECS 201-515-5; NSC 10446; phenanthrene-9,10-quinone; BRN 0608838; SMR000150826; CHEMBL51931; MLS000881132; MLS000571180; AI3-23739; CHEBI:37454; YYVYAPXYZVYDHN-UHFFFAOYSA-N; 42L7BZ8H74; MFCD00001163; 9,10-dihydrophenanthrene-9,10-dione; AK-96664
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 208.21
Logarithm of the Partition Coefficient (xlogp) 2.5
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C14H8O2
IUPAC Name
phenanthrene-9,10-dione
Canonical SMILES
C1=CC=C2C(=C1)C3=CC=CC=C3C(=O)C2=O
InChI
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
Cross-matching ID
PubChem CID
6763
ChEBI ID
CHEMBL37454
CAS Number
84-11-7
TTD ID
D0Q2YJ
INTEDE ID
DR0026
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cholinesterase (BCHE) TTEB0GD CHLE_HUMAN Inhibitor [1]
Liver carboxylesterase (CES1) TTMF541 EST1_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
NADPH-dependent carbonyl reductase 1 (CBR1) DE9JFMC CBR1_HUMAN Substrate [2]
Small intestine reductase (AKR1B10) DEP6GT1 AK1BA_HUMAN Substrate [3]
NADPH-dependent carbonyl reductase 3 (CBR3) DEIVKZ8 CBR3_HUMAN Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aflatoxin B1 aldehyde reductase member 2 (AKR7A2) OTGEDDM2 ARK72_HUMAN Biotransformations [4]
Aldo-keto reductase family 1 member B1 (AKR1B1) OTRX72TH ALDR_HUMAN Biotransformations [4]
Aldo-keto reductase family 1 member B10 (AKR1B10) OTOA4HTH AK1BA_HUMAN Gene/Protein Processing [3]
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Regulation of Drug Effects [5]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Regulation of Drug Effects [5]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [6]
Aldo-keto reductase family 1 member C4 (AKR1C4) OTW2MMOF AK1C4_HUMAN Biotransformations [7]
Bcl-2-binding component 3, isoforms 3/4 (BBC3) OTUAXDAY BBC3B_HUMAN Gene/Protein Processing [6]
Claudin-5 (CLDN5) OTUX60YO CLD5_HUMAN Gene/Protein Processing [8]
Dehydrogenase/reductase SDR family member 11 (DHRS11) OTU3J0ZL DHR11_HUMAN Biotransformations [9]
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Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Liver carboxylesterase (CES1) DTT CES1 3.82E-08 1.86 1.9
Small intestine reductase (AKR1B10) DME AKR1B10 3.34E-03 -1.14E-01 -6.72E-01
NADPH-dependent carbonyl reductase 3 (CBR3) DME CBR3 2.30E-04 -5.58E-01 -1.63E+00
NADPH-dependent carbonyl reductase 1 (CBR1) DME CBR1 2.53E-10 1.09E+00 2.10E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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 Studies on reduction of S-nitrosoglutathione by human carbonyl reductases 1 and 3. Chem Biol Interact. 2011 May 30;191(1-3):95-103.
3 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.
4 Major differences exist in the function and tissue-specific expression of human aflatoxin B1 aldehyde reductase and the principal human aldo-keto reductase AKR1 family members. Biochem J. 1999 Oct 15;343 Pt 2(Pt 2):487-504.
5 An indomethacin analogue, N-(4-chlorobenzoyl)-melatonin, is a selective inhibitor of aldo-keto reductase 1C3 (type 2 3alpha-HSD, type 5 17beta-HSD, and prostaglandin F synthase), a potential target for the treatment of hormone dependent and hormone independent malignancies. Biochem Pharmacol. 2008 Jan 15;75(2):484-93.
6 Facilitation of 9,10-phenanthrenequinone-elicited neuroblastoma cell apoptosis by NAD(P)H:quinone oxidoreductase 1. Chem Biol Interact. 2018 Jan 5;279:10-20.
7 Retinaldehyde is a substrate for human aldo-keto reductases of the 1C subfamily. Biochem J. 2011 Dec 15;440(3):335-44.
8 9,10-Phenanthrenequinone provokes dysfunction of brain endothelial barrier through down-regulating expression of claudin-5. Toxicology. 2021 Sep;461:152896. doi: 10.1016/j.tox.2021.152896. Epub 2021 Aug 12.
9 Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chem Biol Interact. 2019 May 25;305:12-20. doi: 10.1016/j.cbi.2019.03.026. Epub 2019 Mar 26.