Xanthotoxol geranyl ether

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	fbe05dc1-8b14-47a7-b292-237906c20bea
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name	9-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
SMILES (Canonical)	CC(=CCCC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C)C
SMILES (Isomeric)	CC(=CCC/C(=C/COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)/C)C
InChI	InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-19-17(10-12-23-19)13-16-7-8-18(22)25-20(16)21/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
InChI Key	SOVNCTNQAWWYAQ-OQLLNIDSSA-N
Popularity	97 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₁H₂₂O₄
Molecular Weight	338.40 g/mol
Exact Mass	338.15180918 g/mol
Topological Polar Surface Area (TPSA)	48.70 Å²
XlogP	5.30
Atomic LogP (AlogP)	5.61
H-Bond Acceptor	4
H-Bond Donor	0
Rotatable Bonds	6

Synonyms

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7437-55-0

Xanthotoxol geranyl ether

8-Geranyloxy psoralen

9-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-7H-furo[3,2-g]chromen-7-one

71612-25-4

CHEMBL1412710

9-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one

9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one

7H-Furo(3,2-g)(1)benzopyran-7-one, 9-((3,7-dimethyl-2,6-octadienyl)oxy)-

9-((3,7-Dimethylocta-2,6-dien-1-yl)-oxy)-7H-furo[3,2-g]chromen-7-one

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	+	0.6496	64.96%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7975	79.75%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	+	0.9302	93.02%
OATP1B3 inhibitior	+	0.8191	81.91%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9159	91.59%
P-glycoprotein inhibitior	+	0.8682	86.82%
P-glycoprotein substrate	-	0.8787	87.87%
CYP3A4 substrate	-	0.5255	52.55%
CYP2C9 substrate	-	0.6607	66.07%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	+	0.7577	75.77%
CYP2C9 inhibition	+	0.8278	82.78%
CYP2C19 inhibition	+	0.8662	86.62%
CYP2D6 inhibition	+	0.8361	83.61%
CYP1A2 inhibition	+	0.8676	86.76%
CYP2C8 inhibition	-	0.6133	61.33%
CYP inhibitory promiscuity	+	0.7764	77.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5996	59.96%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.7822	78.22%
Skin irritation	-	0.7707	77.07%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8889	88.89%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.8375	83.75%
skin sensitisation	-	0.7862	78.62%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6546	65.46%
Acute Oral Toxicity (c)	III	0.5141	51.41%
Estrogen receptor binding	+	0.6745	67.45%
Androgen receptor binding	+	0.8301	83.01%
Thyroid receptor binding	+	0.6504	65.04%
Glucocorticoid receptor binding	+	0.8559	85.59%
Aromatase binding	+	0.6984	69.84%
PPAR gamma	+	0.8471	84.71%
Honey bee toxicity	-	0.8741	87.41%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	8912.5 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	7943.3 nM	Potency	via CMAUP
CHEMBL4822	P56817	Beta-secretase 1	20400 nM	IC50	PMID: 22222157
CHEMBL340	P08684	Cytochrome P450 3A4	1258.9 nM 1258.9 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	19952.6 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	96.38%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.30%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.06%	92.08%
CHEMBL3401	O75469	Pregnane X receptor	93.63%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.70%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.35%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.53%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.93%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	85.51%	94.75%
CHEMBL4208	P20618	Proteasome component C5	84.45%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.43%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.65%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.60%	97.21%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.60%	94.03%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Angelica archangelica

Angelica dahurica

Artemisia capillaris

Artemisia scoparia

Carpesium abrotanoides

Pleurospermum rivulorum