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

Details

• Internal ID: 6b886338-7eac-40fd-ae12-b2a7a9e8530a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2S,3S,4S,5R,6R)-2-[[(1S,5S,7aS)-5-hydroxy-4-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(C2C1C(OC=C2CO)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C1=C[C@@H](C2[C@H]1[C@@H](OC=C2CO)O[C@H]3[C@H]([C@H]([C@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C15H22O9/c16-3-6-5-22-14(7-1-2-8(18)10(6)7)24-15-13(21)12(20)11(19)9(4-17)23-15/h1-2,5,7-21H,3-4H2/t7-,8-,9+,10?,11-,12-,13-,14-,15-/m0/s1
• InChI Key: RPLYFIDPUPZXQC-VCHDKUBDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.33 g/mol
• Exact Mass: 346.12638228 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -3.00
• Atomic LogP (AlogP): -2.80
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6717	67.17%
Caco-2	-	0.8723	87.23%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5905	59.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8437	84.37%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9542	95.42%
P-glycoprotein inhibitior	-	0.9041	90.41%
P-glycoprotein substrate	-	0.9249	92.49%
CYP3A4 substrate	-	0.5056	50.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8272	82.72%
CYP3A4 inhibition	-	0.9416	94.16%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.7815	78.15%
CYP2D6 inhibition	-	0.8755	87.55%
CYP1A2 inhibition	-	0.8639	86.39%
CYP2C8 inhibition	-	0.8565	85.65%
CYP inhibitory promiscuity	-	0.6978	69.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6579	65.79%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9636	96.36%
Skin irritation	-	0.8209	82.09%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.5063	50.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5136	51.36%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8878	88.78%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.5650	56.50%
Acute Oral Toxicity (c)	IV	0.4268	42.68%
Estrogen receptor binding	-	0.7017	70.17%
Androgen receptor binding	-	0.6335	63.35%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.7325	73.25%
Aromatase binding	+	0.5701	57.01%
PPAR gamma	+	0.5862	58.62%
Honey bee toxicity	-	0.7680	76.80%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	-	0.5621	56.21%

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	95.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.35%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	88.74%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	85.96%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.77%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.69%	97.09%
CHEMBL3589	P55263	Adenosine kinase	82.88%	98.05%

Plants that contains it

• Mentzelia decapetala
• Olearia teretifolia

Cross-Links

• PubChem: 163195594
• LOTUS: LTS0248234
• wikiData: Q105378300