(2R,3S,4R,5S,6R)-2-[[(1S,4aS,5S,6R,7R,7aS)-6-chloro-5,7-dihydroxy-4-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 96e255c4-3c7c-4291-97b6-e7760579a1f9
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3S,4R,5S,6R)-2-[[(1S,4aS,5S,6R,7R,7aS)-6-chloro-5,7-dihydroxy-4-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1=COC(C2C1C(C(C2O)Cl)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC1=CO[C@H]([C@H]2[C@@H]1[C@@H]([C@H]([C@@H]2O)Cl)O)O[C@@H]3[C@H]([C@@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C15H23ClO9/c1-4-3-23-14(7-6(4)10(19)8(16)11(7)20)25-15-13(22)12(21)9(18)5(2-17)24-15/h3,5-15,17-22H,2H2,1H3/t5-,6-,7+,8-,9-,10+,11-,12-,13+,14+,15-/m1/s1
• InChI Key: YIAVDJDCASKRQD-FBKQDDLQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃ClO₉
• Molecular Weight: 382.79 g/mol
• Exact Mass: 382.1030600 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.36
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6745	67.45%
Caco-2	-	0.9000	90.00%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5756	57.56%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.7882	78.82%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8820	88.20%
P-glycoprotein inhibitior	-	0.8819	88.19%
P-glycoprotein substrate	-	0.8982	89.82%
CYP3A4 substrate	+	0.5413	54.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8407	84.07%
CYP3A4 inhibition	-	0.8907	89.07%
CYP2C9 inhibition	-	0.8068	80.68%
CYP2C19 inhibition	-	0.7101	71.01%
CYP2D6 inhibition	-	0.8479	84.79%
CYP1A2 inhibition	-	0.7584	75.84%
CYP2C8 inhibition	-	0.7414	74.14%
CYP inhibitory promiscuity	-	0.5165	51.65%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8838	88.38%
Carcinogenicity (trinary)	Non-required	0.5683	56.83%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9796	97.96%
Skin irritation	-	0.7749	77.49%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6744	67.44%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8668	86.68%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5958	59.58%
Acute Oral Toxicity (c)	III	0.4530	45.30%
Estrogen receptor binding	-	0.6523	65.23%
Androgen receptor binding	-	0.5822	58.22%
Thyroid receptor binding	+	0.5829	58.29%
Glucocorticoid receptor binding	-	0.7148	71.48%
Aromatase binding	+	0.6288	62.88%
PPAR gamma	+	0.6162	61.62%
Honey bee toxicity	-	0.7221	72.21%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.7558	75.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	93.36%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.34%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.30%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.43%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	81.84%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.80%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.62%	86.33%

Plants that contains it

• Mentzelia decapetala

Cross-Links

• PubChem: 163024360
• LOTUS: LTS0262862
• wikiData: Q105348714