5-Hydroxyxanthotoxin

Details

• Internal ID: 5348b933-ebad-437e-a597-cc1f220d20b2
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens > 8-methoxypsoralens
• IUPAC Name: 4-hydroxy-9-methoxyfuro[3,2-g]chromen-7-one
• SMILES (Canonical): COC1=C2C(=C(C3=C1OC=C3)O)C=CC(=O)O2
• SMILES (Isomeric): COC1=C2C(=C(C3=C1OC=C3)O)C=CC(=O)O2
• InChI: InChI=1S/C12H8O5/c1-15-12-10-7(4-5-16-10)9(14)6-2-3-8(13)17-11(6)12/h2-5,14H,1H3
• InChI Key: XPFCGZWOHNGDSP-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₈O₅
• Molecular Weight: 232.19 g/mol
• Exact Mass: 232.03717335 g/mol
• Topological Polar Surface Area (TPSA): 68.90 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 7471-73-0
• 5-hydroxy-8-methoxypsoralen
• 4-hydroxy-9-methoxyfuro[3,2-g]chromen-7-one
• 4-hydroxy-9-methoxy-7H-furo[3,2-g]chromen-7-one
• NSC 401277
• 7H-Furo[3,2-g][1]benzopyran-7-one, 4-hydroxy-9-methoxy-
• 4-hydroxy-9-methoxy-7H-furo[3,2-g]benzopyran-7-one
• 4-Hydroxyisopimpinellin
• NSC401277
• SCHEMBL434686
• CHEBI:2082
• DTXSID70419640
• NSC-401277
• HY-134039
• CS-0137690
• C02951
• E88939
• Q3599225

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9827	98.27%
Caco-2	-	0.6288	62.88%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7043	70.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9065	90.65%
OATP1B3 inhibitior	+	0.9175	91.75%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8307	83.07%
P-glycoprotein inhibitior	-	0.7731	77.31%
P-glycoprotein substrate	-	0.9189	91.89%
CYP3A4 substrate	-	0.5959	59.59%
CYP2C9 substrate	-	0.8431	84.31%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	+	0.6791	67.91%
CYP2C9 inhibition	-	0.7069	70.69%
CYP2C19 inhibition	+	0.7217	72.17%
CYP2D6 inhibition	+	0.7682	76.82%
CYP1A2 inhibition	+	0.8969	89.69%
CYP2C8 inhibition	-	0.6714	67.14%
CYP inhibitory promiscuity	-	0.5489	54.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Warning	0.4683	46.83%
Eye corrosion	-	0.9403	94.03%
Eye irritation	-	0.5838	58.38%
Skin irritation	-	0.6053	60.53%
Skin corrosion	-	0.9789	97.89%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7856	78.56%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.8631	86.31%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8506	85.06%
Acute Oral Toxicity (c)	III	0.7058	70.58%
Estrogen receptor binding	+	0.9269	92.69%
Androgen receptor binding	+	0.6864	68.64%
Thyroid receptor binding	-	0.5186	51.86%
Glucocorticoid receptor binding	+	0.8202	82.02%
Aromatase binding	+	0.5899	58.99%
PPAR gamma	+	0.6899	68.99%
Honey bee toxicity	-	0.9258	92.58%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5756	57.56%
Fish aquatic toxicity	+	0.7930	79.30%

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	98.10%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.14%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.96%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.86%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.82%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.56%	99.23%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.72%	94.03%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.11%	99.17%

Plants that contains it

• Angelica dahurica
• Niphogeton ternata
• Saposhnikovia divaricata

Cross-Links

• PubChem: 5385192
• NPASS: NPC51281
• LOTUS: LTS0154696
• wikiData: Q3599225