Details of the Drug

General Information of Drug (ID: DMTMNO7)

Drug Name

7-hydroxycoumarin

Synonyms

Umbelliferone; 93-35-6; 7-Hydroxy-2H-chromen-2-one; Skimmetin; Hydrangin; 7-hydroxycoumarine; 7-Oxycoumarin; Umbelliferon; Skimmetine; Hydrangine; 2H-1-Benzopyran-2-one, 7-hydroxy-; 7-Hydroxy-2H-1-benzopyran-2-one; Coumarin, 7-hydroxy-; beta-Umbelliferone; 7-hydroxychromen-2-one; 7 HC; UNII-60Z60NTL4G; 7-hydroxy-coumarin; NSC 19790; CCRIS 3591; NSC19790; EINECS 202-240-3; 7H-1-Benzopyran-7-one, 2-hydroxy-; BRN 0127683; CHEMBL51628; AI3-38054; 7-hydroxy-1-benzopyran-2-one; 7-HC; 60Z60NTL4G; CHEBI:27510; UMBELLIFERONE

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

162.14

Logarithm of the Partition Coefficient (xlogp)

1.6

Rotatable Bond Count (rotbonds)

0

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C9H6O3
IUPAC Name: 7-hydroxychromen-2-one
Canonical SMILES: C1=CC(=CC2=C1C=CC(=O)O2)O
InChI: InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
InChIKey: ORHBXUUXSCNDEV-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5281426
ChEBI ID: CHEBI:27510
CAS Number: 93-35-6
TTD ID: D02JEZ

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Carbonic anhydrase IX (CA-IX)	TT2LVK8	CAH9_HUMAN	Inhibitor	[2]
G1/S-specific cyclin-D1 (CCND1)	TTFCJ7S	CCND1_HUMAN	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aflatoxin B1 aldehyde reductase member 2 (AKR7A2)	OTGEDDM2	ARK72_HUMAN	Gene/Protein Processing	[3]
Aflatoxin B1 aldehyde reductase member 3 (AKR7A3)	OTW3GO4Y	ARK73_HUMAN	Gene/Protein Processing	[3]
Aldo-keto reductase family 1 member C3 (AKR1C3)	OTU2SXBA	AK1C3_HUMAN	Gene/Protein Processing	[3]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[4]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[4]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[5]
Cytochrome P450 2A6 (CYP2A6)	OT52TWG3	CP2A6_HUMAN	Biotransformations	[6]
Myeloperoxidase (MPO)	OTOOXLIN	PERM_HUMAN	Biotransformations	[7]
Nuclear factor erythroid 2-related factor 2 (NFE2L2)	OT0HENJ5	NF2L2_HUMAN	Gene/Protein Processing	[3]
Sulfotransferase 1A1 (SULT1A1)	OT0K7JIE	ST1A1_HUMAN	Biotransformations	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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 IX (CA-IX)	DTT	CA9	6.08E-15	2.8	7.25

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Decrease of cyclin D1 in the human lung adenocarcinoma cell line A-427 by 7-hydroxycoumarin. Lung Cancer. 2001 Nov;34(2):185-94.
2	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.
3	Hepatoprotective effect of 7-hydroxycoumarin against methyl glyoxal toxicity via activation of Nrf2. Chem Biol Interact. 2017 Oct 1;276:203-209.
4	Effects of coumarin and 7OH-coumarin on bcl-2 and Bax expression in two human lung cancer cell lines in vitro. Cell Biol Int. 2005 Aug;29(8):703-8. doi: 10.1016/j.cellbi.2005.04.003.
5	Scopoletin and umbelliferone protect hepatocytes against palmitate- and bile acid-induced cell death by reducing endoplasmic reticulum stress and oxidative stress. Toxicol Appl Pharmacol. 2022 Feb 1;436:115858. doi: 10.1016/j.taap.2021.115858. Epub 2021 Dec 31.
6	Metabolism of N-nitrosobenzylmethylamine by human cytochrome P-450 enzymes. J Toxicol Environ Health A. 1999 Dec 10;58(7):397-411.
7	7-Hydroxycoumarin modulates the oxidative metabolism, degranulation and microbial killing of human neutrophils. Chem Biol Interact. 2013 Oct 25;206(1):63-75. doi: 10.1016/j.cbi.2013.08.010. Epub 2013 Aug 28.
8	Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. Drug Metab Dispos. 2001 Mar;29(3):274-81.