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

Details

• Internal ID: a05021c5-e305-4b7e-90cf-da6d71566f3e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5R,7aR)-5-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C14H20O8/c15-5-9-10(17)11(18)12(19)14(21-9)22-13-7-1-2-8(16)6(7)3-4-20-13/h1-4,6-19H,5H2/t6-,7-,8-,9-,10-,11+,12-,13+,14+/m1/s1
• InChI Key: YTUPGVNLNVATQP-PMWMVPJLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₀O₈
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.11581759 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.16
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6950	69.50%
Caco-2	-	0.7664	76.64%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5522	55.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8820	88.20%
OATP1B3 inhibitior	+	0.9669	96.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9789	97.89%
P-glycoprotein inhibitior	-	0.9045	90.45%
P-glycoprotein substrate	-	0.9555	95.55%
CYP3A4 substrate	-	0.5084	50.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8272	82.72%
CYP3A4 inhibition	-	0.9230	92.30%
CYP2C9 inhibition	-	0.9481	94.81%
CYP2C19 inhibition	-	0.8505	85.05%
CYP2D6 inhibition	-	0.8959	89.59%
CYP1A2 inhibition	-	0.9033	90.33%
CYP2C8 inhibition	-	0.8356	83.56%
CYP inhibitory promiscuity	-	0.7954	79.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6517	65.17%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9400	94.00%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9653	96.53%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5600	56.00%
Micronuclear	-	0.7041	70.41%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.9044	90.44%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.4716	47.16%
Acute Oral Toxicity (c)	IV	0.4363	43.63%
Estrogen receptor binding	-	0.8256	82.56%
Androgen receptor binding	-	0.6923	69.23%
Thyroid receptor binding	+	0.5202	52.02%
Glucocorticoid receptor binding	-	0.6458	64.58%
Aromatase binding	-	0.5541	55.41%
PPAR gamma	+	0.6141	61.41%
Honey bee toxicity	-	0.7078	70.78%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.6294	62.94%

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	92.32%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.27%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.58%	86.92%
CHEMBL3589	P55263	Adenosine kinase	81.99%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.00%	97.09%

Plants that contains it

• Retzia capensis

Cross-Links

• PubChem: 163022023
• LOTUS: LTS0089019
• wikiData: Q105362126