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

Details

• Internal ID: 3a5c1934-590b-4d8d-90f4-400925e6d2fc
• 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,7aS)-5-hydroxy-7-methylidene-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C=C1CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C=C1C[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/C15H22O8/c1-6-4-8(17)7-2-3-21-14(10(6)7)23-15-13(20)12(19)11(18)9(5-16)22-15/h2-3,7-20H,1,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
• InChI Key: UQQFHQBHLAWWSL-FKVJWERZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₈
• Molecular Weight: 330.33 g/mol
• Exact Mass: 330.13146766 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.77
• 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	-	0.5521	55.21%
Caco-2	-	0.8766	87.66%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4907	49.07%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.8433	84.33%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9886	98.86%
P-glycoprotein inhibitior	-	0.9004	90.04%
P-glycoprotein substrate	-	0.8982	89.82%
CYP3A4 substrate	+	0.5265	52.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8125	81.25%
CYP3A4 inhibition	-	0.8569	85.69%
CYP2C9 inhibition	-	0.9160	91.60%
CYP2C19 inhibition	-	0.8208	82.08%
CYP2D6 inhibition	-	0.8702	87.02%
CYP1A2 inhibition	-	0.8707	87.07%
CYP2C8 inhibition	-	0.8235	82.35%
CYP inhibitory promiscuity	-	0.8282	82.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7119	71.19%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9387	93.87%
Skin irritation	-	0.7859	78.59%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5994	59.94%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	-	0.8177	81.77%
skin sensitisation	-	0.8569	85.69%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.5705	57.05%
Acute Oral Toxicity (c)	III	0.4150	41.50%
Estrogen receptor binding	-	0.6520	65.20%
Androgen receptor binding	-	0.6007	60.07%
Thyroid receptor binding	+	0.5492	54.92%
Glucocorticoid receptor binding	-	0.6806	68.06%
Aromatase binding	+	0.6000	60.00%
PPAR gamma	+	0.6684	66.84%
Honey bee toxicity	-	0.7711	77.11%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	-	0.4270	42.70%

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	97.55%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.51%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.28%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.17%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	81.85%	95.93%

Plants that contains it

• Linaria japonica

Cross-Links

• PubChem: 163016844
• LOTUS: LTS0242888
• wikiData: Q105277397