Geranyloxy-coumarin

Details

• Internal ID: 116a7522-6ee9-4ce8-a359-4035d8d8c9fb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 3-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
• SMILES (Canonical): CC(=CCCC(=CCOC1=CC2=CC=CC=C2OC1=O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/COC1=CC2=CC=CC=C2OC1=O)/C)C
• InChI: InChI=1S/C19H22O3/c1-14(2)7-6-8-15(3)11-12-21-18-13-16-9-4-5-10-17(16)22-19(18)20/h4-5,7,9-11,13H,6,8,12H2,1-3H3/b15-11+
• InChI Key: OADHUMKVIIISRJ-RVDMUPIBSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.40 g/mol
• Exact Mass: 298.15689456 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.86
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• geranyloxy-coumarin
• BDBM50391169

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9928	99.28%
Caco-2	+	0.8093	80.93%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8504	85.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9325	93.25%
OATP1B3 inhibitior	+	0.9193	91.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8563	85.63%
P-glycoprotein inhibitior	+	0.5775	57.75%
P-glycoprotein substrate	-	0.9045	90.45%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6607	66.07%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	-	0.7412	74.12%
CYP2C9 inhibition	+	0.6794	67.94%
CYP2C19 inhibition	+	0.9060	90.60%
CYP2D6 inhibition	-	0.6441	64.41%
CYP1A2 inhibition	+	0.9374	93.74%
CYP2C8 inhibition	-	0.6958	69.58%
CYP inhibitory promiscuity	+	0.7783	77.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6714	67.14%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.6228	62.28%
Skin irritation	-	0.8160	81.60%
Skin corrosion	-	0.9670	96.70%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8221	82.21%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.7700	77.00%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.5495	54.95%
Acute Oral Toxicity (c)	III	0.4715	47.15%
Estrogen receptor binding	+	0.6987	69.87%
Androgen receptor binding	+	0.6816	68.16%
Thyroid receptor binding	+	0.5901	59.01%
Glucocorticoid receptor binding	+	0.5775	57.75%
Aromatase binding	+	0.6998	69.98%
PPAR gamma	+	0.7525	75.25%
Honey bee toxicity	-	0.8854	88.54%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.98%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	96.29%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.67%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.92%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.85%	98.95%
CHEMBL2039	P27338	Monoamine oxidase B	92.20%	92.51%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.47%	92.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.60%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.95%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.69%	96.95%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.76%	93.65%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.61%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.14%	95.50%
CHEMBL4208	P20618	Proteasome component C5	80.05%	90.00%

Plants that contains it

• Citrus × aurantium

Cross-Links

• PubChem: 46841210
• LOTUS: LTS0254886
• wikiData: Q105188622