2-Isopropenyl-2,3-dihydrofuro[3,2-g]chromen-7-one

Details

• Internal ID: 7561bd81-7c4f-4ac2-933a-76216702d6cf
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: 2-prop-1-en-2-yl-2,3-dihydrofuro[3,2-g]chromen-7-one
• SMILES (Canonical): CC(=C)C1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3
• SMILES (Isomeric): CC(=C)C1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3
• InChI: InChI=1S/C14H12O3/c1-8(2)11-6-10-5-9-3-4-14(15)17-12(9)7-13(10)16-11/h3-5,7,11H,1,6H2,2H3
• InChI Key: VMWUHWZFDITAOL-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24 g/mol
• Exact Mass: 228.078644241 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 2-Isopropenyl-2,3-dihydrofuro[3,2-g]chromen-7-one
• 2-(prop-1-en-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
• TimTec1_006449
• Oprea1_325209
• 55658-11-2
• MLS000560893
• 2-Isopropenyl-2,3-dihydro-furo[3,2-g]chromen-7-one
• CHEMBL1467672
• VMWUHWZFDITAOL-UHFFFAOYSA-N
• HMS1552F03
• HMS2535G16
• STK396318
• AKOS000546786
• AKOS022060440
• SMR000173762
• AB00278866-10
• 2-(prop-1-en-2-yl)-2h-furo[3,2-g]chromene-7(3 h)-one
• 2-Isopropenyl-2,3-dihydro-7H-furo[3,2-g]chromen-7-one #
• 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-methylethenyl)-
• InChI=1/C14H12O3/c1-8(2)11-6-10-5-9-3-4-14(15)17-12(9)7-13(10)16-11/h3-5,7,11H,1,6H2,2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7397	73.97%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6811	68.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9316	93.16%
OATP1B3 inhibitior	+	0.9697	96.97%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7094	70.94%
P-glycoprotein inhibitior	-	0.8486	84.86%
P-glycoprotein substrate	-	0.7780	77.80%
CYP3A4 substrate	-	0.5815	58.15%
CYP2C9 substrate	-	0.6607	66.07%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	+	0.5747	57.47%
CYP2C9 inhibition	+	0.5892	58.92%
CYP2C19 inhibition	+	0.8499	84.99%
CYP2D6 inhibition	-	0.7782	77.82%
CYP1A2 inhibition	+	0.8670	86.70%
CYP2C8 inhibition	-	0.9291	92.91%
CYP inhibitory promiscuity	+	0.7579	75.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4854	48.54%
Eye corrosion	-	0.9629	96.29%
Eye irritation	+	0.6153	61.53%
Skin irritation	-	0.5799	57.99%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4234	42.34%
Micronuclear	+	0.5959	59.59%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	+	0.5419	54.19%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6415	64.15%
Acute Oral Toxicity (c)	III	0.4034	40.34%
Estrogen receptor binding	-	0.6145	61.45%
Androgen receptor binding	-	0.5489	54.89%
Thyroid receptor binding	-	0.6135	61.35%
Glucocorticoid receptor binding	-	0.7269	72.69%
Aromatase binding	+	0.6578	65.78%
PPAR gamma	-	0.4869	48.69%
Honey bee toxicity	-	0.8536	85.36%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9914	99.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	25118.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	22387.2 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	7.1 nM; 7.1 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	2511.9 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	96.24%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	92.87%	91.49%
CHEMBL2581	P07339	Cathepsin D	92.52%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.97%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.67%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	85.39%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.20%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.05%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.93%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.31%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.05%	95.56%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.40%	85.11%

Plants that contains it

• Ammi majus
• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Stauranthus perforatus

Cross-Links

• PubChem: 611672
• NPASS: NPC234109
• ChEMBL: CHEMBL1467672
• LOTUS: LTS0248079
• wikiData: Q103813471