(10R)-5-hydroxy-6-[(2R,3S)-3-hydroxy-2-methylbutanoyl]-2,2-dimethyl-10-propyl-9,10-dihydropyrano[2,3-f]chromen-8-one

Details

• Internal ID: a57f104b-d1c8-4199-9bb9-c208c47c620b
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: (10R)-5-hydroxy-6-[(2R,3S)-3-hydroxy-2-methylbutanoyl]-2,2-dimethyl-10-propyl-9,10-dihydropyrano[2,3-f]chromen-8-one
• InChI: InChI=1S/C22H28O6/c1-6-7-13-10-15(24)27-21-16(13)20-14(8-9-22(4,5)28-20)19(26)17(21)18(25)11(2)12(3)23/h8-9,11-13,23,26H,6-7,10H2,1-5H3/t11-,12+,13-/m1/s1
• InChI Key: QVXVUACNNIWBIU-FRRDWIJNSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₆
• Molecular Weight: 388.50 g/mol
• Exact Mass: 388.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.97
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9645	96.45%
Caco-2	+	0.5498	54.98%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8006	80.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7956	79.56%
OATP1B3 inhibitior	+	0.9055	90.55%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6942	69.42%
P-glycoprotein inhibitior	-	0.6470	64.70%
P-glycoprotein substrate	+	0.5806	58.06%
CYP3A4 substrate	+	0.6130	61.30%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8533	85.33%
CYP3A4 inhibition	-	0.6884	68.84%
CYP2C9 inhibition	-	0.6838	68.38%
CYP2C19 inhibition	-	0.8296	82.96%
CYP2D6 inhibition	-	0.9260	92.60%
CYP1A2 inhibition	-	0.7780	77.80%
CYP2C8 inhibition	+	0.4636	46.36%
CYP inhibitory promiscuity	-	0.8352	83.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5737	57.37%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8441	84.41%
Skin irritation	-	0.7507	75.07%
Skin corrosion	-	0.9283	92.83%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6388	63.88%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6790	67.90%
skin sensitisation	-	0.7702	77.02%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8115	81.15%
Acute Oral Toxicity (c)	III	0.6463	64.63%
Estrogen receptor binding	+	0.7330	73.30%
Androgen receptor binding	+	0.6042	60.42%
Thyroid receptor binding	+	0.5134	51.34%
Glucocorticoid receptor binding	+	0.8322	83.22%
Aromatase binding	+	0.5979	59.79%
PPAR gamma	+	0.8378	83.78%
Honey bee toxicity	-	0.8732	87.32%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9917	99.17%

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	99.03%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.64%	97.25%
CHEMBL2581	P07339	Cathepsin D	97.63%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.25%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.35%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.59%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.80%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.02%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.67%	93.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.21%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.10%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	83.24%	90.17%
CHEMBL4208	P20618	Proteasome component C5	81.36%	90.00%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	80.39%	95.34%

Plants that contains it

• Calophyllum lanigerum

Cross-Links

• PubChem: 124708199
• LOTUS: LTS0052707
• wikiData: Q105228994