(4R,8R)-5-hydroxy-4,8-diphenyl-3,4,7,8-tetrahydropyrano[3,2-g]chromene-2,6-dione

Details

• Internal ID: 139da5d5-9c00-40cb-97ef-accd31a00ab7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Pyranoflavonoids
• IUPAC Name: (4R,8R)-5-hydroxy-4,8-diphenyl-3,4,7,8-tetrahydropyrano[3,2-g]chromene-2,6-dione
• SMILES (Canonical): C1C(C2=C(C3=C(C=C2OC1=O)OC(CC3=O)C4=CC=CC=C4)O)C5=CC=CC=C5
• SMILES (Isomeric): C1[C@@H](C2=C(C3=C(C=C2OC1=O)O[C@H](CC3=O)C4=CC=CC=C4)O)C5=CC=CC=C5
• InChI: InChI=1S/C24H18O5/c25-17-12-18(15-9-5-2-6-10-15)28-20-13-19-22(24(27)23(17)20)16(11-21(26)29-19)14-7-3-1-4-8-14/h1-10,13,16,18,27H,11-12H2/t16-,18-/m1/s1
• InChI Key: ZNAYOLWBEXMRIR-SJLPKXTDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₁₈O₅
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.11542367 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.54
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9562	95.62%
Caco-2	-	0.7702	77.02%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8202	82.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8985	89.85%
OATP1B3 inhibitior	+	0.9858	98.58%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.7882	78.82%
P-glycoprotein inhibitior	+	0.7245	72.45%
P-glycoprotein substrate	-	0.9087	90.87%
CYP3A4 substrate	-	0.5111	51.11%
CYP2C9 substrate	+	0.7996	79.96%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.7864	78.64%
CYP2C9 inhibition	+	0.8350	83.50%
CYP2C19 inhibition	-	0.8023	80.23%
CYP2D6 inhibition	-	0.8915	89.15%
CYP1A2 inhibition	-	0.8145	81.45%
CYP2C8 inhibition	+	0.5967	59.67%
CYP inhibitory promiscuity	-	0.9043	90.43%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.5736	57.36%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.6707	67.07%
Skin irritation	-	0.5605	56.05%
Skin corrosion	-	0.9675	96.75%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5283	52.83%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9099	90.99%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7457	74.57%
Acute Oral Toxicity (c)	II	0.4467	44.67%
Estrogen receptor binding	+	0.7967	79.67%
Androgen receptor binding	+	0.7406	74.06%
Thyroid receptor binding	-	0.5282	52.82%
Glucocorticoid receptor binding	+	0.6871	68.71%
Aromatase binding	-	0.6160	61.60%
PPAR gamma	+	0.8154	81.54%
Honey bee toxicity	-	0.8823	88.23%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8944	89.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.01%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.36%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.40%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.37%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.63%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.84%	97.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.53%	85.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.79%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.57%	85.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.72%	93.00%

Plants that contains it

• Pityrogramma calomelanos

Cross-Links

• PubChem: 163039860
• LOTUS: LTS0064337
• wikiData: Q105379909