Xanthotoxol

Details

• Internal ID: 3312b81c-0e12-4173-9f66-2ed217dc6429
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens > 8-hydroxypsoralens
• IUPAC Name: 9-hydroxyfuro[3,2-g]chromen-7-one
• SMILES (Canonical): C1=CC(=O)OC2=C(C3=C(C=CO3)C=C21)O
• SMILES (Isomeric): C1=CC(=O)OC2=C(C3=C(C=CO3)C=C21)O
• InChI: InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H
• InChI Key: JWVYQQGERKEAHW-UHFFFAOYSA-N
• Popularity: 216 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: 1.60
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 8-Hydroxypsoralen
• 2009-24-7
• 8-Hydroxypsoralene
• Psoralen, 8-hydroxy-
• 8-Hydroxyfuranocoumarin
• 9-Hydroxy-7H-furo[3,2-g]chromen-7-one
• 9-hydroxyfuro[3,2-g]chromen-7-one
• 7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-
• XANTHOTOL
• 9-Hydroxy-7H-furo(3,2-g)(1)benzopyran-7-one
• NSC 401269
• Xanthotoxol (6CI)
• C11H6O4
• EINECS 217-923-1
• NSC401269
• 7H-Furo[3,2-g][1]benzopyran-7-one,9-hydroxy-
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy-
• BRN 0189491
• 6,7-Dihydroxy-5-benzofuranacrylic acid gamma-lactone
• CHEBI:15709
• 8RL486L8A5
• 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one
• NSC-401269
• 5-Benzofuranacrylic acid, 6,7-dihydroxy-, gamma-lactone
• 5-19-06-00014 (Beilstein Handbook Reference)
• 5-Benzofuranacrylic acid, 6,7-dihydroxy-, .delta.-lactone
• 2-Propenoic acid, 3-(6,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone
• 8-hydroxy-psoralen
• 8-Hydroxyanthotoxol
• 8-hydroxyfurocoumarin
• 8-hydroxyfurocoumarins
• 9-hydroxy-furo[3,2-g]chromen-7-one
• Xanthotol; Xanthotoxol
• 8-hydroxyfuranocoumarins
• an 8-hydroxyfurocoumarin
• 7H-Furo[3, 9-hydroxy-
• CHEMBL1192
• MLS002472938
• SCHEMBL499269
• UNII-8RL486L8A5
• DTXSID50173910
• HMS2267B05
• HMS3886P18
• BDBM50361378
• MFCD00017408
• s9174
• AKOS000276803
• CCG-266594
• CS-8023
• CS-T-46622
• NCGC00247457-01
• AC-12979
• AC-34294
• BS-21947
• HY-30152
• LS-70724
• SMR001397046
• 9-hydroxy-2H-furo[3,2-g]chromen-2-one
• FT-0633974
• 9-Hydroxy-7H-furo[3,2-g]chromen-7-one #
• A14771
• C00841
• H10450
• A879846
• Q4021722
• W-201757
• 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CI
• 2-Propenoic acid,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone
• 6-(3,4-Dichlorophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
• InChI=1/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9831	98.31%
Caco-2	+	0.7898	78.98%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6525	65.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9234	92.34%
OATP1B3 inhibitior	+	0.8978	89.78%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8706	87.06%
P-glycoprotein inhibitior	-	0.9239	92.39%
P-glycoprotein substrate	-	0.9750	97.50%
CYP3A4 substrate	-	0.7171	71.71%
CYP2C9 substrate	-	0.8392	83.92%
CYP2D6 substrate	-	0.8390	83.90%
CYP3A4 inhibition	+	0.6270	62.70%
CYP2C9 inhibition	-	0.7372	73.72%
CYP2C19 inhibition	-	0.6555	65.55%
CYP2D6 inhibition	-	0.5847	58.47%
CYP1A2 inhibition	+	0.8392	83.92%
CYP2C8 inhibition	-	0.8311	83.11%
CYP inhibitory promiscuity	-	0.8041	80.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Warning	0.4364	43.64%
Eye corrosion	-	0.9608	96.08%
Eye irritation	+	0.5283	52.83%
Skin irritation	+	0.6777	67.77%
Skin corrosion	-	0.9817	98.17%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8077	80.77%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.7960	79.60%
skin sensitisation	-	0.7505	75.05%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7488	74.88%
Acute Oral Toxicity (c)	II	0.7376	73.76%
Estrogen receptor binding	+	0.7953	79.53%
Androgen receptor binding	+	0.7644	76.44%
Thyroid receptor binding	+	0.5388	53.88%
Glucocorticoid receptor binding	+	0.8027	80.27%
Aromatase binding	+	0.8867	88.67%
PPAR gamma	+	0.8820	88.20%
Honey bee toxicity	-	0.9516	95.16%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8696	86.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.24%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.44%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.53%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.75%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.44%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.12%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.28%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	84.93%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.40%	89.00%

Plants that contains it

• Angelica archangelica
• Angelica dahurica
• Angelica japonica
• Angelica saxatilis
• Archidendron chevalieri
• Casimiroa edulis
• Clausena anisata
• Clausena lansium
• Cnidium monnieri
• Ferula moschata
• Foeniculum vulgare
• Glehnia littoralis
• Hansenia weberbaueriana
• Pastinaca sativa
• Peucedanum japonicum
• Peucedanum rubricaule
• Pleurospermum rivulorum
• Prangos uloptera
• Rhadinothamnus rudis
• Skimmia laureola
• Torilis japonica
• Trifolium pratense
• Zanthoxylum spinosum

Cross-Links

• PubChem: 65090
• NPASS: NPC15819
• ChEMBL: CHEMBL1192
• LOTUS: LTS0086962
• wikiData: Q4021722