Details of the Drug

General Information of Drug (ID: DM0N8ZM)

Drug Name
COUMARIN
Synonyms
coumarin; 2H-Chromen-2-one; 91-64-5; 2H-1-Benzopyran-2-one; cumarin; 1,2-Benzopyrone; Rattex; Tonka bean camphor; Coumarinic anhydride; chromen-2-one; Coumarine; Benzo-alpha-pyrone; cis-o-Coumarinic acid lactone; o-Hydroxycinnamic acid lactone; o-Hydroxycinnamic lactone; 2-Oxo-1,2-benzopyran; Coumarinic lactone; Kumarin; Benzo-a-pyrone; Kumarin [Czech]; 5,6-Benzo-2-pyrone; 2H-1-Benzopyran, 2-oxo-; 5,6-Benzo-alpha-pyrone; 2H-Benzo(b)pyran-2-one; 2H-Benzo[b]pyran-2-one; Caswell No. 259C; o-Coumaric acid lactone
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) 146.14
Logarithm of the Partition Coefficient (xlogp) 1.4
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 23.6 mL/min/kg [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.8 hours [2]
Unbound Fraction
The unbound fraction of drug in plasma is 0.17% [2]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.1 L/kg [2]
Chemical Identifiers
Formula
C9H6O2
IUPAC Name
chromen-2-one
Canonical SMILES
C1=CC=C2C(=C1)C=CC(=O)O2
InChI
InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
InChIKey
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
323
ChEBI ID
CHEBI:28794
CAS Number
91-64-5
DrugBank ID
DB04665
TTD ID
D03ZMQ
VARIDT ID
DR00864
INTEDE ID
DR0386

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Carbonic anhydrase (CA) TTUNARX NOUNIPROTAC Inhibitor [1]
Carbonic anhydrase I (CA-I) TTHQPL7 CAH1_HUMAN Inhibitor [3]
Carbonic anhydrase II (CA-II) TTANPDJ CAH2_HUMAN Inhibitor [3]
Carbonic anhydrase IV (CA-IV) TTZHA0O CAH4_HUMAN Inhibitor [1]
Carbonic anhydrase IX (CA-IX) TT2LVK8 CAH9_HUMAN Inhibitor [1]
Carbonic anhydrase VI (CA-VI) TTCFSPE CAH6_HUMAN Inhibitor [1]
Carbonic anhydrase XII (CA-XII) TTSYM0R CAH12_HUMAN Inhibitor [1]
Carbonic anhydrase XIV (CA-XIV) TTEYTKG CAH14_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]
Cytochrome P450 102D1 (cyp102) DEUWAV0 CPXB_BACMB Substrate [5], [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
(E3-independent) E2 ubiquitin-conjugating enzyme OTHGS2VA UBE2O_HUMAN Post-Translational Modifications [7]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3 (PLCD3) OTB22A4J PLCD3_HUMAN Post-Translational Modifications [7]
17S U2 SnRNP complex component HTATSF1 (HTATSF1) OTLQ1ZLS HTSF1_HUMAN Post-Translational Modifications [7]
182 kDa tankyrase-1-binding protein (TNKS1BP1) OTBIZECQ TB182_HUMAN Post-Translational Modifications [7]
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial (BCKDHA) OT0LHOZB ODBA_HUMAN Post-Translational Modifications [7]
2-phosphoxylose phosphatase 1 (PXYLP1) OTX8T7F6 PXYP1_HUMAN Post-Translational Modifications [7]
26S proteasome regulatory subunit 6A (PSMC3) OTSKT0JI PRS6A_HUMAN Post-Translational Modifications [7]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 (HSD3B1) OTNAZVKB 3BHS1_HUMAN Post-Translational Modifications [7]
3',5'-cyclic-AMP phosphodiesterase 4D (PDE4D) OT1RWFV0 PDE4D_HUMAN Post-Translational Modifications [7]
3',5'-cyclic-AMP phosphodiesterase 7B (PDE7B) OTK3SHT2 PDE7B_HUMAN Post-Translational Modifications [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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
Carbonic anhydrase IV (CA-IV) DTT CA4 1.58E-77 -2.02 -1.77
Carbonic anhydrase XII (CA-XII) DTT CA12 3.29E-21 1.27 1.02
Carbonic anhydrase I (CA-I) DTT CA1 5.23E-14 -0.11 -0.41
Carbonic anhydrase XIV (CA-XIV) DTT CA14 5.79E-07 -0.09 -0.16
Carbonic anhydrase VI (CA-VI) DTT CA6 3.64E-10 -0.17 -0.37
Carbonic anhydrase II (CA-II) DTT CA2 7.95E-08 0.52 0.33
Carbonic anhydrase IX (CA-IX) DTT CA9 1.12E-10 -0.03 -0.09
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 1.07E-11 -1.16E-01 -2.53E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem. 2010 Jan 14;53(1):335-44.
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and X... Bioorg Med Chem Lett. 2010 Dec 15;20(24):7255-8.
4 Pharmacogenomics of CYP2C9: functional and clinical considerations. J Pers Med. 2017 Dec 28;8(1).
5 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
6 Cloning, expression and characterization of CYP102D1, a self-sufficient P450 monooxygenase from Streptomyces avermitilis. FEBS J. 2012 May;279(9):1650-62.
7 Quantitative phosphoproteomics reveal cellular responses from caffeine, coumarin and quercetin in treated HepG2 cells. Toxicol Appl Pharmacol. 2022 Aug 15;449:116110. doi: 10.1016/j.taap.2022.116110. Epub 2022 Jun 7.