Chalepensin

Details

• Internal ID: 484bd4d9-ce48-4380-98a0-21984f83b47b
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: 6-(2-methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one
• SMILES (Canonical): CC(C)(C=C)C1=CC2=C(C=C3C(=C2)C=CO3)OC1=O
• SMILES (Isomeric): CC(C)(C=C)C1=CC2=C(C=C3C(=C2)C=CO3)OC1=O
• InChI: InChI=1S/C16H14O3/c1-4-16(2,3)12-8-11-7-10-5-6-18-13(10)9-14(11)19-15(12)17/h4-9H,1H2,2-3H3
• InChI Key: FYCCCUNGXGKNJV-UHFFFAOYSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28 g/mol
• Exact Mass: 254.094294304 g/mol
• Topological Polar Surface Area (TPSA): 39.40 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.00
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 13164-03-9
• 3-(alpha,alpha-Dimethylallyl)psoralen
• Xyloltenin
• 6-(2-methylbut-3-en-2-yl)-7h-furo[3,2-g]chromen-7-one
• 6-(2-methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one
• CHEBI:3572
• 6-(1,1-Dimethylallyl)-7H-furo(3,2-g)(1)benzopyran-7-one
• 6-(1,1-Dimethyl-2-propenyl)-7H-furo(3,2-g)(1)benzopyran-7-one
• 6-(1-1-Dimethyl-2-propenyl)-7H-furo(3,2-g)(1)benzopyran-7-one
• 6-(1,1-dimethylallyl)furo[3,2-g]chromen-7-one
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 6-(1,1-dimethylallyl)-
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 6-(1,1-dimethyl-2-propenyl)-
• SMR000156206
• Dimethyl allyl psoralene
• TGU8MP93CA
• MLS000574854
• MLS000876991
• MEGxp0_000992
• CHEMBL1333931
• SCHEMBL15941545
• ACon1_001036
• DTXSID90157153
• FYCCCUNGXGKNJV-UHFFFAOYSA-N
• HMS2202C08
• HMS3352N04
• AKOS040761478
• NCGC00169737-01
• LS-70716
• C09165
• Psoralen, 3-(.alpha.,.alpha.-dimethylallyl)-
• BRD-K01892695-001-01-2
• Q27106137
• 6-(1,1-Dimethyl-2-propen-1-yl)-7H-furo[3,2-g][1]benzopyran-7-one
• 7H-Furo[3,2-g][1]benzopyran-7-one, 6-(1,1-dimethyl-2-propen-1-yl)-
• InChI=1/C16H14O3/c1-4-16(2,3)12-8-11-7-10-5-6-18-13(10)9-14(11)19-15(12)17/h4-9H,1H2,2-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.7789	77.89%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7684	76.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9328	93.28%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6488	64.88%
P-glycoprotein inhibitior	-	0.6213	62.13%
P-glycoprotein substrate	-	0.8396	83.96%
CYP3A4 substrate	-	0.5638	56.38%
CYP2C9 substrate	-	0.6657	66.57%
CYP2D6 substrate	-	0.8660	86.60%
CYP3A4 inhibition	+	0.8424	84.24%
CYP2C9 inhibition	+	0.5572	55.72%
CYP2C19 inhibition	+	0.6688	66.88%
CYP2D6 inhibition	-	0.8125	81.25%
CYP1A2 inhibition	+	0.6100	61.00%
CYP2C8 inhibition	-	0.8126	81.26%
CYP inhibitory promiscuity	+	0.6252	62.52%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.4045	40.45%
Eye corrosion	-	0.9783	97.83%
Eye irritation	-	0.6668	66.68%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9062	90.62%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6806	68.06%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	+	0.4940	49.40%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5250	52.50%
Acute Oral Toxicity (c)	II	0.4719	47.19%
Estrogen receptor binding	+	0.8844	88.44%
Androgen receptor binding	+	0.6749	67.49%
Thyroid receptor binding	+	0.5999	59.99%
Glucocorticoid receptor binding	+	0.6854	68.54%
Aromatase binding	+	0.8991	89.91%
PPAR gamma	+	0.5590	55.90%
Honey bee toxicity	-	0.8599	85.99%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9938	99.38%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.52%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.36%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.66%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.35%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.17%	95.56%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.77%	93.65%
CHEMBL1951	P21397	Monoamine oxidase A	85.51%	91.49%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.47%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.32%	94.00%

Plants that contains it

• Boenninghausenia albiflora
• Clausena lansium
• Psilopeganum sinense
• Ruta chalepensis
• Ruta graveolens
• Ruta montana
• Stauranthus perforatus

Cross-Links

• PubChem: 128834
• NPASS: NPC266743
• ChEMBL: CHEMBL1333931
• LOTUS: LTS0091876
• wikiData: Q27106137