(5R,7S)-4,7-dimethyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-cyclopenta[c]pyran-1-one

Details

• Internal ID: 9355faf9-4d61-4f84-a70e-75edb29f9d49
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (5R,7S)-4,7-dimethyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-cyclopenta[c]pyran-1-one
• InChI: InChI=1S/C16H22O8/c1-6-3-8(10-7(2)5-22-15(21)11(6)10)23-16-14(20)13(19)12(18)9(4-17)24-16/h5-6,8-9,12-14,16-20H,3-4H2,1-2H3/t6-,8+,9+,12+,13-,14+,16+/m0/s1
• InChI Key: VLYVYBNJXMTERV-UDJIVENISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₈
• Molecular Weight: 342.34 g/mol
• Exact Mass: 342.13146766 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -0.69
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4737	47.37%
Caco-2	-	0.8289	82.89%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6518	65.18%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.8747	87.47%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8118	81.18%
P-glycoprotein inhibitior	-	0.8047	80.47%
P-glycoprotein substrate	-	0.8859	88.59%
CYP3A4 substrate	+	0.5962	59.62%
CYP2C9 substrate	-	0.6095	60.95%
CYP2D6 substrate	-	0.8667	86.67%
CYP3A4 inhibition	-	0.8614	86.14%
CYP2C9 inhibition	-	0.8709	87.09%
CYP2C19 inhibition	-	0.8541	85.41%
CYP2D6 inhibition	-	0.9299	92.99%
CYP1A2 inhibition	-	0.6976	69.76%
CYP2C8 inhibition	-	0.8058	80.58%
CYP inhibitory promiscuity	-	0.7220	72.20%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6758	67.58%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9701	97.01%
Skin irritation	-	0.8117	81.17%
Skin corrosion	-	0.9577	95.77%
Ames mutagenesis	-	0.5263	52.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6175	61.75%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.7109	71.09%
skin sensitisation	-	0.8570	85.70%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8156	81.56%
Acute Oral Toxicity (c)	III	0.6140	61.40%
Estrogen receptor binding	+	0.5412	54.12%
Androgen receptor binding	+	0.6390	63.90%
Thyroid receptor binding	-	0.5531	55.31%
Glucocorticoid receptor binding	+	0.6773	67.73%
Aromatase binding	-	0.6078	60.78%
PPAR gamma	+	0.5567	55.67%
Honey bee toxicity	-	0.8232	82.32%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8482	84.82%

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	95.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.49%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.03%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.22%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.25%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.03%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.33%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	84.32%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.73%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.49%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.19%	86.92%

Plants that contains it

• Nepeta racemosa

Cross-Links

• PubChem: 10617255
• LOTUS: LTS0002931
• wikiData: Q105288845