5-Geranyloxy-7-methoxycoumarin

Details

• Internal ID: a55f5a4a-c4b9-4dc3-870b-df55868305c0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 5-[(2E)-3,7-dimethylocta-2,6-dienoxy]-7-methoxychromen-2-one
• SMILES (Canonical): CC(=CCCC(=CCOC1=CC(=CC2=C1C=CC(=O)O2)OC)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/COC1=CC(=CC2=C1C=CC(=O)O2)OC)/C)C
• InChI: InChI=1S/C20H24O4/c1-14(2)6-5-7-15(3)10-11-23-18-12-16(22-4)13-19-17(18)8-9-20(21)24-19/h6,8-10,12-13H,5,7,11H2,1-4H3/b15-10+
• InChI Key: WXUOSNJWDJOHGW-XNTDXEJSSA-N
• Popularity: 31 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.87
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 5-geranyloxy-7-methoxycoumarin
• 5-(Geranyloxy)-7-methoxycoumarin
• Herniarin, 5-(geranyloxy)-
• 5-(Geranyloxy)-Herniarin
• Coumarin, 5-((3,7-dimethyl-2,6-octadienyl)oxy)-7-methoxy-, (E)
• 5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-2H-chromen-2-one
• 2H-1-Benzopyran-2-one, 5-((3,7-dimethyl-2,6-octadienyl)oxy)-7-methoxy-, (E)-
• 5-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-7-methoxy-2H-chromen-2-one
• RefChem:102693
• QWPLVRCHBYSUDX-CXUHLZMHSA-N
• 7380-39-4
• 7-Methoxy-5-geranoxycoumarin
• 5-[(2E)-3,7-dimethylocta-2,6-dienoxy]-7-methoxychromen-2-one
• MFCD00210506
• (E)-5-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-7-methoxy-2H-chromen-2-one
• 39A7K6NN3W
• 5-((3,7-Dimethyl-2,6-octadienyl)oxy)-7-methoxycoumarin
• UNII-39A7K6NN3W
• orb1297131
• SCHEMBL1714204
• CHEMBL4176013
• SCHEMBL31135288
• CHEBI:174428
• DTXSID001045382
• HY-N8431
• AKOS027381401
• DA-70203
• TS-10136
• XG163780
• CS-0144151
• ST50331498
• Q13461252
• 5-((2E)-3,7-dimethylocta-2,6-dienyloxy)-7-methoxychromen-2-one
• 5-[(2E)-3,7-dimethylocta-2,6-dienoxy]-7-methoxy-chromen-2-one
• Coumarin, 5-[(3,7-dimethyl-2,6-octadienyl)oxy]-7-methoxy-, (E)-
• 2H-1-Benzopyran-2-one, 5-[(3,7-dimethyl-2,6-octadien-1-yl)oxy]-7-methoxy-
• 2H-1-Benzopyran-2-one, 5-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-7-methoxy-
• 5-[(3,7-Dimethyl-2,6-octadien-1-yl)oxy]-7-methoxy-2H-1-benzopyran-2-one
• 5-[[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy]-7-methoxy-2H-1-benzopyran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.8097	80.97%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7374	73.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9295	92.95%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9413	94.13%
P-glycoprotein inhibitior	+	0.7780	77.80%
P-glycoprotein substrate	-	0.7899	78.99%
CYP3A4 substrate	+	0.5314	53.14%
CYP2C9 substrate	-	0.6607	66.07%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	+	0.5525	55.25%
CYP2C9 inhibition	+	0.6357	63.57%
CYP2C19 inhibition	+	0.8900	89.00%
CYP2D6 inhibition	-	0.5119	51.19%
CYP1A2 inhibition	+	0.9226	92.26%
CYP2C8 inhibition	-	0.6119	61.19%
CYP inhibitory promiscuity	+	0.6916	69.16%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7213	72.13%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.8783	87.83%
Skin irritation	-	0.8306	83.06%
Skin corrosion	-	0.9740	97.40%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8456	84.56%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8159	81.59%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7282	72.82%
Acute Oral Toxicity (c)	III	0.5503	55.03%
Estrogen receptor binding	+	0.8707	87.07%
Androgen receptor binding	+	0.8861	88.61%
Thyroid receptor binding	+	0.5678	56.78%
Glucocorticoid receptor binding	+	0.8384	83.84%
Aromatase binding	+	0.7731	77.31%
PPAR gamma	+	0.7938	79.38%
Honey bee toxicity	-	0.8749	87.49%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	98.60%	91.11%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	97.30%	92.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.76%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.63%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	92.60%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.37%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.79%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.81%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.30%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.08%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.53%	90.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.25%	94.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.60%	96.09%
CHEMBL2535	P11166	Glucose transporter	82.42%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.32%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.26%	95.89%

Plants that contains it

• Hansenia weberbaueriana

Cross-Links

• PubChem: 6441377
• NPASS: NPC290764
• LOTUS: LTS0081520
• wikiData: Q13461252