Bergaptol

Details

• Internal ID: 7509a9a8-6d9f-45f5-ac60-f77caa4a83c1
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens > 5-hydroxypsoralens
• IUPAC Name: 4-hydroxyfuro[3,2-g]chromen-7-one
• SMILES (Canonical): C1=CC(=O)OC2=CC3=C(C=CO3)C(=C21)O
• SMILES (Isomeric): C1=CC(=O)OC2=CC3=C(C=CO3)C(=C21)O
• InChI: InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
• InChI Key: GIJHDGJRTUSBJR-UHFFFAOYSA-N
• Popularity: 149 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₆O₄
• Molecular Weight: 202.16 g/mol
• Exact Mass: 202.02660867 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 486-60-2
• 5-Hydroxypsoralen
• 4-Hydroxy-7H-furo[3,2-g]chromen-7-one
• 5-Hydroxyfuranocoumarin
• 4-Hydroxybergapten
• Psoralin, 5-hydroxy-
• 4-hydroxyfuro[3,2-g]chromen-7-one
• 7H-Furo[3,2-g][1]benzopyran-7-one, 4-hydroxy-
• UNII-KTC8ANI30F
• NSC341958
• KTC8ANI30F
• NSC 341958
• CHEMBL242711
• CHEBI:17377
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy-
• 5-Hydroxypsoralen;4-Hydroxybergapten
• 4-oxidanylfuro[3,2-g]chromen-7-one
• NSC-341958
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy- (8CI)(9CI)
• Bergaptols
• 5-Hydroxy-6,7-furanocoumarin
• 4-Hydroxypsoralen
• 5-Hydroxy-Psoralen
• 5-Hydroxyfurocoumarin
• 5-HYDROXY-PSORALIN
• D0D5YP
• 7H-Furo[3, 4-hydroxy-
• 4-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one
• BSPBio_002390
• MLS002472898
• Bergaptol, analytical standard
• SCHEMBL194016
• SPECTRUM1505137
• DTXSID40197564
• HMS2270B20
• BCP30863
• CS-M0862
• BDBM50209569
• MFCD00210479
• s9442
• 4-Hydroxybergapten; 5-Hydroxypsoralen
• AKOS022646985
• CCG-266595
• NCGC00096026-01
• NCGC00096026-02
• NCGC00178678-01
• AC-34217
• AS-56064
• HY-76316
• SMR001397009
• 5-hydroxy-2H-furo[3,2-g]chromen-2-one
• FT-0663072
• 4-Hydroxy-7H-furo[3,2-g]chromen-7-one #
• 4-Hydroxy7H-furo[3,2-g][1]benzopyran-7-one
• C00758
• A827582
• SR-05000002443
• Q3638533
• SR-05000002443-1
• BRD-K36383661-001-01-1
• Z1509594645
• {7H-Furo[3,} {2-g][1]benzopyran-7-one,} 4-hydroxy-
• 4-Hydroxy-7H-furo[3,2-g]chromen-7-one (ACD/Name 4.0)
• 8B6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.7481	74.81%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6509	65.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8681	86.81%
OATP1B3 inhibitior	+	0.9525	95.25%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8460	84.60%
P-glycoprotein inhibitior	-	0.9157	91.57%
P-glycoprotein substrate	-	0.9431	94.31%
CYP3A4 substrate	-	0.6514	65.14%
CYP2C9 substrate	-	0.8392	83.92%
CYP2D6 substrate	-	0.8390	83.90%
CYP3A4 inhibition	+	0.7125	71.25%
CYP2C9 inhibition	+	0.5558	55.58%
CYP2C19 inhibition	-	0.5918	59.18%
CYP2D6 inhibition	-	0.5564	55.64%
CYP1A2 inhibition	+	0.8327	83.27%
CYP2C8 inhibition	-	0.7985	79.85%
CYP inhibitory promiscuity	-	0.8069	80.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Warning	0.3877	38.77%
Eye corrosion	-	0.9569	95.69%
Eye irritation	+	0.9004	90.04%
Skin irritation	+	0.7074	70.74%
Skin corrosion	-	0.9863	98.63%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8611	86.11%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.8158	81.58%
skin sensitisation	-	0.8113	81.13%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8852	88.52%
Acute Oral Toxicity (c)	II	0.6190	61.90%
Estrogen receptor binding	+	0.9374	93.74%
Androgen receptor binding	+	0.8563	85.63%
Thyroid receptor binding	+	0.5869	58.69%
Glucocorticoid receptor binding	+	0.8799	87.99%
Aromatase binding	+	0.8890	88.90%
PPAR gamma	+	0.7672	76.72%
Honey bee toxicity	-	0.9276	92.76%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5756	57.56%
Fish aquatic toxicity	+	0.8970	89.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL5282	P11509	Cytochrome P450 2A6	11600 nM	Ki	PMID: 16248836
CHEMBL340	P08684	Cytochrome P450 3A4	24920 nM	IC50	PMID: 17400460
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.96%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.29%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.93%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.37%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.79%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.39%	98.95%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	87.17%	94.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.21%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.03%	90.71%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.79%	93.65%

Plants that contains it

• Angelica archangelica
• Angelica dahurica
• Angelica dahurica var. formosana
• Citrus × aurantium
• Citrus maxima
• Citrus medica
• Dorstenia contrajerva
• Hansenia forbesii
• Hansenia weberbaueriana
• Prangos platychlaena
• Ruta montana
• Seseli buchtormense
• Skimmia laureola
• Tordylium apulum
• Zanthoxylum spinosum

Cross-Links

• PubChem: 5280371
• NPASS: NPC155882
• ChEMBL: CHEMBL242711
• LOTUS: LTS0144228
• wikiData: Q3638533