Psoralidin

Details

• Internal ID: d61468ad-779c-47a7-aec5-c337ef6423f3
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Coumestans
• IUPAC Name: 3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one
• SMILES (Canonical): CC(=CCC1=CC2=C(C=C1O)OC(=O)C3=C2OC4=C3C=CC(=C4)O)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C=C1O)OC(=O)C3=C2OC4=C3C=CC(=C4)O)C
• InChI: InChI=1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3
• InChI Key: YABIJLLNNFURIJ-UHFFFAOYSA-N
• Popularity: 63 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₆O₅
• Molecular Weight: 336.30 g/mol
• Exact Mass: 336.09977361 g/mol
• Topological Polar Surface Area (TPSA): 79.90 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.61
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 18642-23-4
• 3,9-Dihydroxy-2-prenylcoumestan
• UNII-G16ZUQ069L
• G16ZUQ069L
• 3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one
• 3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro(3,2-c)(1)benzopyran-6-one
• CHEBI:8616
• DTXSID20171903
• 3,9-Dihydroxy-2-(3-methylbut-2-en-1-yl)-6H-benzofuro[3,2-c]chromen-6-one
• 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-2-(3-methyl-2-butenyl)-
• 3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one
• 3,9-dihydroxy-2-(3-methylbut-2-en-1-yl)-6H-(1)benzofuro(3,2-c)(1)benzopyran-6-one
• 3,9-dihydroxy-2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c][1]benzopyran-6-one
• 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-2-(3-methyl-2-butenyl)-
• Psoralidin (5)
• C20H16O5
• PSORALIDIN [MI]
• SCHEMBL3239072
• CHEMBL4064323
• DTXCID2094394
• BDBM246524
• HY-N0232
• LMPK12090007
• MFCD10566617
• s5464
• AKOS026674261
• CCG-267867
• CS-3757
• 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-2-(3-methyl-2-buten-1-yl)-
• NCGC00388431-05
• 3-benzofurancarboxylic acid, 2-(2,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-6-hydroxy-, delta-lactone
• AC-34016
• AS-18741
• FT-0688287
• P2605
• EN300-6730959
• A921802
• Q-100223
• Q7256115
• 3-BENZOFURANCARBOXYLIC ACID, 2-(2,4-DIHYDROXY-5-(3-METHYL-2-BUTENYL)PHENYL)-6-HYDROXY-, .DELTA.-LACTONE
• 5,14-dihydroxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.4930	49.30%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8383	83.83%
OATP2B1 inhibitior	-	0.5664	56.64%
OATP1B1 inhibitior	+	0.8921	89.21%
OATP1B3 inhibitior	+	0.9059	90.59%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7746	77.46%
P-glycoprotein inhibitior	-	0.5509	55.09%
P-glycoprotein substrate	-	0.6266	62.66%
CYP3A4 substrate	-	0.5178	51.78%
CYP2C9 substrate	-	0.5505	55.05%
CYP2D6 substrate	-	0.8400	84.00%
CYP3A4 inhibition	-	0.5872	58.72%
CYP2C9 inhibition	+	0.9323	93.23%
CYP2C19 inhibition	+	0.8389	83.89%
CYP2D6 inhibition	-	0.6963	69.63%
CYP1A2 inhibition	+	0.6801	68.01%
CYP2C8 inhibition	-	0.6651	66.51%
CYP inhibitory promiscuity	+	0.8490	84.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4976	49.76%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.6293	62.93%
Skin irritation	-	0.6825	68.25%
Skin corrosion	-	0.9345	93.45%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6554	65.54%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.6581	65.81%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6860	68.60%
Acute Oral Toxicity (c)	III	0.4195	41.95%
Estrogen receptor binding	+	0.9145	91.45%
Androgen receptor binding	+	0.8825	88.25%
Thyroid receptor binding	+	0.5628	56.28%
Glucocorticoid receptor binding	+	0.8904	89.04%
Aromatase binding	+	0.7834	78.34%
PPAR gamma	+	0.9327	93.27%
Honey bee toxicity	-	0.8759	87.59%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9969	99.69%

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	99.42%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.27%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	95.84%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.90%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.14%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.05%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.51%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.85%	91.71%
CHEMBL1951	P21397	Monoamine oxidase A	87.95%	91.49%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.96%	83.57%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.56%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	84.93%	98.35%
CHEMBL3194	P02766	Transthyretin	83.99%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.71%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.08%	99.15%

Plants that contains it

• Cullen corylifolium
• Phaseolus lunatus

Cross-Links

• PubChem: 5281806
• NPASS: NPC242755
• LOTUS: LTS0057633
• wikiData: Q7256115