urolithin B

Details

• Internal ID: ec45f305-2a9c-438f-b092-9c9655017534
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 3-hydroxybenzo[c]chromen-6-one
• SMILES (Canonical): C1=CC=C2C(=C1)C3=C(C=C(C=C3)O)OC2=O
• SMILES (Isomeric): C1=CC=C2C(=C1)C3=C(C=C(C=C3)O)OC2=O
• InChI: InChI=1S/C13H8O3/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)16-12(10)7-8/h1-7,14H
• InChI Key: WXUQMTRHPNOXBV-UHFFFAOYSA-N
• Popularity: 120 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₃
• Molecular Weight: 212.20 g/mol
• Exact Mass: 212.047344113 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 1139-83-9
• 3-hydroxy-6H-benzo[c]chromen-6-one
• 3-hydroxybenzo[c]chromen-6-one
• 3-HYDROXY-6H-DIBENZO[B,D]PYRAN-6-ONE
• 3-Hydroxyurolithin
• 7-hydroxy-3,4-benzocoumarin
• B1S2YM5F6G
• 6H-Dibenzo(b,d)pyran-6-one, 3-hydroxy-
• 6H-Dibenzo[b,d]pyran-6-one, 3-hydroxy-
• CHEMBL1526978
• 3-Hydroxy-benzo[c]chromen-6-one
• MFCD00034338
• NSC 94726
• NSC-94726
• SMR000125059
• 3-HYDROXY-6H-BENZO(C)CHROMEN-6-ONE
• 3-HYDROXY-6H-DIBENZO(B,D)PYRAN-6-ONE
• urolithinB
• NSC94726
• 3-hydroxy-urolithin
• 3-Hydroxydibenzo-a-pyrone
• UNII-B1S2YM5F6G
• NCIOpen2_005982
• Oprea1_202205
• Oprea1_232259
• CBDivE_012154
• MLS000067644
• MLS001049038
• SCHEMBL4420540
• 3-hydroxy-6-benzo[c]chromenone
• DTXSID00150610
• CHEBI:166606
• WXUQMTRHPNOXBV-UHFFFAOYSA-N
• HMS2172E20
• HMS3319J06
• NP755
• Urolithin B, >=95% (HPLC)
• BBL027918
• BDBM50521706
• NSC823879
• s1321
• STK086550
• AKOS000274161
• DS-9071
• NSC-823879
• 3-HYDROXYDIBENZO-.ALPHA.-PYRONE
• NCGC00245498-01
• NCGC00245498-02
• AC-34553
• HY-126307
• CS-0101847
• FT-0778245
• EN300-186402
• 3-Hydroxy-6H-benzo[c]chromen-6-one, AldrichCPR
• A920658
• J-003044
• Q18395107
• Z57108866
• 2-BIPHENYLCARBOXYLIC ACID, 2',4'-DIHYDROXY-, .DELTA.-LACTONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	-	0.6337	63.37%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5575	55.75%
OATP2B1 inhibitior	-	0.8666	86.66%
OATP1B1 inhibitior	+	0.8536	85.36%
OATP1B3 inhibitior	+	0.9858	98.58%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8528	85.28%
P-glycoprotein inhibitior	-	0.9017	90.17%
P-glycoprotein substrate	-	0.9219	92.19%
CYP3A4 substrate	-	0.5909	59.09%
CYP2C9 substrate	-	0.8392	83.92%
CYP2D6 substrate	-	0.8390	83.90%
CYP3A4 inhibition	-	0.8380	83.80%
CYP2C9 inhibition	-	0.8700	87.00%
CYP2C19 inhibition	-	0.7922	79.22%
CYP2D6 inhibition	-	0.9420	94.20%
CYP1A2 inhibition	+	0.8298	82.98%
CYP2C8 inhibition	-	0.7310	73.10%
CYP inhibitory promiscuity	-	0.9069	90.69%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.4671	46.71%
Eye corrosion	-	0.9232	92.32%
Eye irritation	+	0.9921	99.21%
Skin irritation	+	0.8174	81.74%
Skin corrosion	-	0.9909	99.09%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8941	89.41%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.7792	77.92%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7324	73.24%
Acute Oral Toxicity (c)	III	0.5546	55.46%
Estrogen receptor binding	+	0.9557	95.57%
Androgen receptor binding	+	0.9306	93.06%
Thyroid receptor binding	+	0.6931	69.31%
Glucocorticoid receptor binding	+	0.9367	93.67%
Aromatase binding	+	0.9471	94.71%
PPAR gamma	+	0.8610	86.10%
Honey bee toxicity	-	0.8893	88.93%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8563	85.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	5011.9 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	98.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.37%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	93.04%	83.57%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.76%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.10%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.78%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.85%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.02%	94.00%
CHEMBL2535	P11166	Glucose transporter	81.40%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.07%	86.33%

Plants that contains it

• Punica granatum

Cross-Links

• PubChem: 5380406
• NPASS: NPC254994
• ChEMBL: CHEMBL1526978
• LOTUS: LTS0150979
• wikiData: Q18395107