3-Hydroxycoumarin

Details

• Internal ID: 7cdc4bd7-faf8-4e15-ae70-450b1beca783
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins
• IUPAC Name: 3-hydroxychromen-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C=C(C(=O)O2)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C=C(C(=O)O2)O
• InChI: InChI=1S/C9H6O3/c10-7-5-6-3-1-2-4-8(6)12-9(7)11/h1-5,10H
• InChI Key: MJKVTPMWOKAVMS-UHFFFAOYSA-N
• Popularity: 858 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₆O₃
• Molecular Weight: 162.14 g/mol
• Exact Mass: 162.031694049 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.50
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 939-19-5
• 3-hydroxy-2H-chromen-2-one
• 3-hydroxychromen-2-one
• 3-Hydroxy-2-benzopyrone
• hydroxycoumarin
• 3 Hydroxycoumarin
• 2H-1-Benzopyran-2-one, 3-hydroxy-
• 3-Hydroxy-2H-1-benzopyran-2-one
• 3-Hydroxy-chromen-2-one
• COUMARIN, 3-HYDROXY-
• RQX0CMD9PN
• UNII-RQX0CMD9PN
• EINECS 213-355-3
• NSC 74691
• BRN 0128032
• CHEMBL150372
• NSC-74691
• 5-18-01-00376 (Beilstein Handbook Reference)
• 3-hydroxy-coumarin
• 3-hydroxychromenone
• NSC74691
• 43070-85-5
• Spectrum_000476
• 3-COUMARINOL
• SpecPlus_000860
• Spectrum2_000805
• Spectrum3_001267
• Spectrum4_001576
• Spectrum5_000232
• hydroxy-2H-chromen-2-one
• SCHEMBL76090
• BSPBio_002834
• KBioGR_002132
• KBioSS_000956
• SPECTRUM211538
• DivK1c_006956
• SPBio_000669
• KBio1_001900
• KBio2_000956
• KBio2_003524
• KBio2_006092
• KBio3_002334
• DTXSID50239863
• CHEBI:113542
• MJKVTPMWOKAVMS-UHFFFAOYSA-N
• o-Hydroxyphenylpyruvic acid lactone
• 2H-1-Benzopyran-2-one,3-hydroxy-
• BDBM50206007
• CCG-39664
• MFCD00017490
• AKOS015916452
• SDCCGMLS-0066523.P001
• NCGC00095536-01
• NCGC00095536-02
• NCGC00178445-01
• AMY202100133
• LS-55208
• MS-22894
• PD002122
• HY-127170
• CS-0094421
• FT-0633159
• H1585
• 2H-1-Benzopyran-2-one, 3-hydroxy- (9CI)
• T73087
• AN-829/40355682
• BRD-K92019075-001-02-0
• Q27194434

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	+	0.7766	77.66%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7524	75.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9405	94.05%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9037	90.37%
P-glycoprotein inhibitior	-	0.9691	96.91%
P-glycoprotein substrate	-	0.9904	99.04%
CYP3A4 substrate	-	0.7089	70.89%
CYP2C9 substrate	-	0.8392	83.92%
CYP2D6 substrate	-	0.8390	83.90%
CYP3A4 inhibition	-	0.9484	94.84%
CYP2C9 inhibition	-	0.5781	57.81%
CYP2C19 inhibition	-	0.8864	88.64%
CYP2D6 inhibition	-	0.9279	92.79%
CYP1A2 inhibition	+	0.5876	58.76%
CYP2C8 inhibition	-	0.9357	93.57%
CYP inhibitory promiscuity	-	0.8716	87.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5438	54.38%
Eye corrosion	-	0.9694	96.94%
Eye irritation	+	0.9948	99.48%
Skin irritation	+	0.8464	84.64%
Skin corrosion	-	0.9848	98.48%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8565	85.65%
Micronuclear	+	0.8018	80.18%
Hepatotoxicity	+	0.6803	68.03%
skin sensitisation	-	0.5886	58.86%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6506	65.06%
Acute Oral Toxicity (c)	II	0.4413	44.13%
Estrogen receptor binding	-	0.6816	68.16%
Androgen receptor binding	-	0.6142	61.42%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6271	62.71%
Aromatase binding	+	0.5334	53.34%
PPAR gamma	+	0.6967	69.67%
Honey bee toxicity	-	0.9518	95.18%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9274	92.74%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	17782.8 nM	Potency	via CMAUP
CHEMBL5485	P14920	D-amino-acid oxidase	943 nM; 440 nM; 34.67 nM; 13 nM	IC50; IC50; IC50; Ki	PMID: 23391306; PMID: 23391306; PMID: 23631755; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.60%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.57%	95.56%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.32%	93.65%
CHEMBL2581	P07339	Cathepsin D	87.25%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	87.22%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.88%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.74%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.29%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.77%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.42%	89.00%

Plants that contains it

• Alyxia reinwardtii
• Capsicum annuum
• Holarrhena pubescens
• Laggera crispata
• Morus alba

Cross-Links

• PubChem: 13650
• NPASS: NPC266116
• ChEMBL: CHEMBL150372
• LOTUS: LTS0221152
• wikiData: Q27194434