Uralenol

Details

• Internal ID: c51048db-a8a5-4288-97b0-ab84b2e6b0f6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 3-prenylated flavones
• IUPAC Name: 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3,5,7-trihydroxychromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O)C
• InChI: InChI=1S/C20H18O7/c1-9(2)3-4-10-5-11(6-14(23)17(10)24)20-19(26)18(25)16-13(22)7-12(21)8-15(16)27-20/h3,5-8,21-24,26H,4H2,1-2H3
• InChI Key: WOMWVGHYSNATOB-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₇
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.10525291 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 139163-15-8
• 3,5,7,3',4'-Pentahydroxy-5'-isoprenylflavone
• 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3,5,7-trihydroxychromen-4-one
• DTXSID50160946
• 2-(3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl)-3,5,7-trihydroxychromen-4-one
• RefChem:193179
• DTXCID3083437
• CHEMBL113833
• 2-(3,4-Dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl)-3,5,7-trihydroxy-4H-chromen-4-one
• orb1984280
• SCHEMBL1170912
• SCHEMBL30266817
• CHEBI:175758
• HY-N9326
• PFA16315
• BDBM50121024
• LMPK12112286
• AKOS040760741
• DA-68491
• MS-25950
• PD197613
• 3',4',5,7-Tetrahydroxy-5'-prenylflavonol
• CS-0159467
• F90322
• 2-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one
• 2-[3,4-Dihydroxy-5-(3-methyl-but-2-enyl)-phenyl]-3,5,7-trihydroxy-chromen-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl)-3,5,7-trihydroxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9557	95.57%
Caco-2	+	0.5166	51.66%
Blood Brain Barrier	-	0.6879	68.79%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6353	63.53%
OATP2B1 inhibitior	-	0.5294	52.94%
OATP1B1 inhibitior	+	0.8036	80.36%
OATP1B3 inhibitior	+	0.9799	97.99%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8097	80.97%
P-glycoprotein inhibitior	-	0.6493	64.93%
P-glycoprotein substrate	-	0.6048	60.48%
CYP3A4 substrate	+	0.5602	56.02%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8389	83.89%
CYP3A4 inhibition	-	0.6386	63.86%
CYP2C9 inhibition	+	0.8814	88.14%
CYP2C19 inhibition	+	0.7647	76.47%
CYP2D6 inhibition	-	0.6149	61.49%
CYP1A2 inhibition	+	0.8104	81.04%
CYP2C8 inhibition	+	0.8257	82.57%
CYP inhibitory promiscuity	+	0.8620	86.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7063	70.63%
Eye corrosion	-	0.9903	99.03%
Eye irritation	+	0.6005	60.05%
Skin irritation	-	0.7140	71.40%
Skin corrosion	-	0.8999	89.99%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3946	39.46%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.6198	61.98%
skin sensitisation	-	0.7492	74.92%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6641	66.41%
Acute Oral Toxicity (c)	III	0.4936	49.36%
Estrogen receptor binding	+	0.9344	93.44%
Androgen receptor binding	+	0.7753	77.53%
Thyroid receptor binding	-	0.5098	50.98%
Glucocorticoid receptor binding	+	0.8585	85.85%
Aromatase binding	+	0.6694	66.94%
PPAR gamma	+	0.9183	91.83%
Honey bee toxicity	-	0.8808	88.08%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9938	99.38%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	21500 nM	IC50	PMID: 12419367

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.61%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	96.68%	94.73%
CHEMBL2581	P07339	Cathepsin D	96.47%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.79%	96.12%
CHEMBL1951	P21397	Monoamine oxidase A	95.59%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.18%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.82%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.66%	95.64%
CHEMBL3194	P02766	Transthyretin	88.63%	90.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.61%	91.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.19%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.60%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.59%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.13%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.36%	90.71%
CHEMBL2424	Q04760	Glyoxalase I	80.14%	91.67%

Plants that contains it

• Broussonetia papyrifera
• Glycyrrhiza
• Glycyrrhiza uralensis

Cross-Links

• PubChem: 5315126
• NPASS: NPC205046
• ChEMBL: CHEMBL113833
• LOTUS: LTS0125555
• wikiData: Q83029301