(8R,9R)-5,9-dihydroxy-2,2-dimethyl-10-oxo-8-phenyl-8,9-dihydropyrano[2,3-f]chromene-6-carbaldehyde

Details

• Internal ID: d52dea99-46eb-4c5b-b230-8a33a1b69f5f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Pyranoflavonoids
• IUPAC Name: (8R,9R)-5,9-dihydroxy-2,2-dimethyl-10-oxo-8-phenyl-8,9-dihydropyrano[2,3-f]chromene-6-carbaldehyde
• SMILES (Canonical): CC1(C=CC2=C(C(=C3C(=C2O1)C(=O)C(C(O3)C4=CC=CC=C4)O)C=O)O)C
• SMILES (Isomeric): CC1(C=CC2=C(C(=C3C(=C2O1)C(=O)[C@@H]([C@H](O3)C4=CC=CC=C4)O)C=O)O)C
• InChI: InChI=1S/C21H18O6/c1-21(2)9-8-12-15(23)13(10-22)19-14(20(12)27-21)16(24)17(25)18(26-19)11-6-4-3-5-7-11/h3-10,17-18,23,25H,1-2H3/t17-,18+/m0/s1
• InChI Key: UGWRCDURVAJLKZ-ZWKOTPCHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₆
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.11033829 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9787	97.87%
Caco-2	+	0.5466	54.66%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8500	85.00%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.7663	76.63%
OATP1B3 inhibitior	+	0.9649	96.49%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8515	85.15%
P-glycoprotein inhibitior	+	0.6274	62.74%
P-glycoprotein substrate	-	0.7745	77.45%
CYP3A4 substrate	+	0.5936	59.36%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.5829	58.29%
CYP2C9 inhibition	+	0.8967	89.67%
CYP2C19 inhibition	+	0.5622	56.22%
CYP2D6 inhibition	-	0.8835	88.35%
CYP1A2 inhibition	-	0.7584	75.84%
CYP2C8 inhibition	+	0.4842	48.42%
CYP inhibitory promiscuity	+	0.5136	51.36%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5370	53.70%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.4869	48.69%
Skin irritation	-	0.6964	69.64%
Skin corrosion	-	0.9029	90.29%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.5801	58.01%
skin sensitisation	-	0.7999	79.99%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6001	60.01%
Acute Oral Toxicity (c)	III	0.6895	68.95%
Estrogen receptor binding	+	0.7867	78.67%
Androgen receptor binding	+	0.6005	60.05%
Thyroid receptor binding	+	0.6975	69.75%
Glucocorticoid receptor binding	+	0.8416	84.16%
Aromatase binding	-	0.5997	59.97%
PPAR gamma	+	0.7046	70.46%
Honey bee toxicity	-	0.8716	87.16%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9833	98.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.12%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.35%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.49%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.13%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.66%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.34%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	88.12%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.22%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.21%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.67%	86.33%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	83.55%	98.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.51%	96.09%

Plants that contains it

• Dunbaria longiracemosa

Cross-Links

• PubChem: 54763533
• LOTUS: LTS0042477
• wikiData: Q105272618