4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)-

Details

• Internal ID: 62fc4f1a-fcb8-46b7-ab99-e67ec2bb6302
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: (2R)-5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
• SMILES (Isomeric): C1[C@@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
• InChI: InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2/t13-/m1/s1
• InChI Key: URFCJEUYXNAHFI-CYBMUJFWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25 g/mol
• Exact Mass: 256.07355886 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• (R)-PINOCEMBRIN
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)-
• (2R)-5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
• (R)-5,7-Dihydroxy-2-phenylchroman-4-one
• (2R)-5,7-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
• pinocembrine
• (2R)-5,7-dihydroxy-2-phenylchroman-4-one
• (R)-5,7-dihydroxyflavanone
• CHEMBL399249
• SCHEMBL10080882
• BDBM26666
• DTXSID30349853
• URFCJEUYXNAHFI-CYBMUJFWSA-N
• TNP00071
• AKOS030254805
• NCGC00017205-01
• NCGC00017205-02
• NCGC00142377-01
• (2R)-5,7-dihydroxy-2-phenyl-chroman-4-one
• A14759
• A836234
• Q63395297

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9450	94.50%
Caco-2	+	0.5248	52.48%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7583	75.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9604	96.04%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8313	83.13%
P-glycoprotein inhibitior	-	0.8983	89.83%
P-glycoprotein substrate	-	0.9692	96.92%
CYP3A4 substrate	-	0.5805	58.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	+	0.8988	89.88%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.7463	74.63%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.4941	49.41%
CYP inhibitory promiscuity	+	0.7121	71.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.9920	99.20%
Eye irritation	+	0.9580	95.80%
Skin irritation	-	0.5127	51.27%
Skin corrosion	-	0.9616	96.16%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6626	66.26%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8697	86.97%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6455	64.55%
Acute Oral Toxicity (c)	II	0.3682	36.82%
Estrogen receptor binding	+	0.7210	72.10%
Androgen receptor binding	+	0.6394	63.94%
Thyroid receptor binding	-	0.5096	50.96%
Glucocorticoid receptor binding	+	0.5789	57.89%
Aromatase binding	+	0.7123	71.23%
PPAR gamma	+	0.8225	82.25%
Honey bee toxicity	-	0.8838	88.38%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.7714	77.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1978	P11511	Cytochrome P450 19A1	900 nM	IC50	via Super-PRED
CHEMBL3622	P33261	Cytochrome P450 2C19	631 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	12589.3 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	19952.6 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	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	98.78%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.86%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.66%	99.23%
CHEMBL2581	P07339	Cathepsin D	91.95%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.48%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.78%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.19%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.62%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.49%	96.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.09%	96.12%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.33%	85.11%
CHEMBL4208	P20618	Proteasome component C5	80.47%	90.00%

Plants that contains it

• Alpinia zerumbet
• Boesenbergia rotunda
• Broussonetia papyrifera
• Dalbergia odorifera
• Euphorbia hirta
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Helichrysum italicum
• Humulus lupulus
• Lepechinia caulescens
• Maprounea guianensis
• Oroxylum indicum
• Peritassa campestris
• Piper nigrum
• Polygonatum zanlanscianense
• Pseudotsuga sinensis var. sinensis
• Pteris cretica subsp. cretica
• Punica granatum
• Rhododendron dauricum
• Syzygium samarangense

Cross-Links

• PubChem: 667544
• NPASS: NPC13768
• ChEMBL: CHEMBL399249
• LOTUS: LTS0049658
• wikiData: Q63395297