Ulopterol

Details

• Internal ID: 77f50fa7-c946-464f-855f-531f9e2bc29b
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 6-[(2R)-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one
• SMILES (Canonical): CC(C)(C(CC1=C(C=C2C(=C1)C=CC(=O)O2)OC)O)O
• SMILES (Isomeric): CC(C)([C@@H](CC1=C(C=C2C(=C1)C=CC(=O)O2)OC)O)O
• InChI: InChI=1S/C15H18O5/c1-15(2,18)13(16)7-10-6-9-4-5-14(17)20-12(9)8-11(10)19-3/h4-6,8,13,16,18H,7H2,1-3H3/t13-/m1/s1
• InChI Key: BNLKKFPQJANWMM-CYBMUJFWSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.48
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 28095-18-3
• Peucedanol methyl ether
• (+)-Ulopterol
• 6-[(2R)-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one
• Coumarin, 6-(2,3-dihydroxy-3-methylbutyl)-7-methoxy-
• 6-(2,3-Dihydroxy-3-methylbutyl)-7-methoxycoumarin
• Ulopterol; 6-(2,3-Dihydroxy-3-methylbutyl)-7-methoxycoumarin
• (R)-6-(2,3-Dihydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one
• DTXSID20950831
• HY-N0080
• MFCD17676155
• CS-0007120
• A14852
• Q-100357
• 6-(2,3-dihydroxy-3-methylbutyl)-7-methoxy-2H-1-benzopyran-2-one
• 2H-1-Benzopyran-2-one, 6-(2,3-dihydroxy-3-methylbutyl)-7-methoxy-, (R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9581	95.81%
Caco-2	+	0.7288	72.88%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6297	62.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	+	0.8647	86.47%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6440	64.40%
P-glycoprotein inhibitior	-	0.9322	93.22%
P-glycoprotein substrate	-	0.7720	77.20%
CYP3A4 substrate	-	0.5585	55.85%
CYP2C9 substrate	-	0.6381	63.81%
CYP2D6 substrate	-	0.8025	80.25%
CYP3A4 inhibition	-	0.9407	94.07%
CYP2C9 inhibition	-	0.9529	95.29%
CYP2C19 inhibition	-	0.9249	92.49%
CYP2D6 inhibition	-	0.9233	92.33%
CYP1A2 inhibition	+	0.5899	58.99%
CYP2C8 inhibition	-	0.7455	74.55%
CYP inhibitory promiscuity	-	0.9533	95.33%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6533	65.33%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.8655	86.55%
Skin irritation	-	0.7684	76.84%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3879	38.79%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.6194	61.94%
skin sensitisation	-	0.8650	86.50%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.5926	59.26%
Acute Oral Toxicity (c)	III	0.6265	62.65%
Estrogen receptor binding	+	0.6468	64.68%
Androgen receptor binding	-	0.5388	53.88%
Thyroid receptor binding	-	0.5220	52.20%
Glucocorticoid receptor binding	+	0.5670	56.70%
Aromatase binding	+	0.5316	53.16%
PPAR gamma	+	0.8252	82.52%
Honey bee toxicity	-	0.8494	84.94%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9399	93.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.98%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.68%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.60%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.01%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.36%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	89.02%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.61%	99.17%
CHEMBL2535	P11166	Glucose transporter	87.60%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.98%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.70%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.79%	89.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.74%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.25%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.75%	96.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.27%	96.00%

Plants that contains it

• Amyris diatrypa
• Amyris lineata
• Angelica dahurica
• Angelica pachycarpa
• Angelica pubescens
• Baccharis pedunculata
• Cachrys sicula
• Citrus maxima
• Coleonema album
• Peucedanum japonicum
• Prangos pabularia
• Prangos uloptera
• Skimmia laureola
• Toddalia asiatica

Cross-Links

• PubChem: 176475
• NPASS: NPC176383
• LOTUS: LTS0068882
• wikiData: Q72500726