(1S,4aS,5R,7R,7aR)-5-hydroxy-7-methyl-1-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: bf38fa24-6f57-46cd-8780-4259b8961651
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Hexoses
• IUPAC Name: (1S,4aS,5R,7R,7aR)-5-hydroxy-7-methyl-1-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1CC(C2C1C(OC=C2C(=O)O)OC3C(OC(C(C3O)O)O)CO)O
• SMILES (Isomeric): C[C@@H]1C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O)CO)O
• InChI: InChI=1S/C16H24O10/c1-5-2-7(18)10-6(14(21)22)4-24-16(9(5)10)26-13-8(3-17)25-15(23)12(20)11(13)19/h4-5,7-13,15-20,23H,2-3H2,1H3,(H,21,22)/t5-,7-,8-,9-,10+,11-,12-,13-,15-,16+/m1/s1
• InChI Key: NVCZOHBDSQMFSL-LVLPPMPYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.36 g/mol
• Exact Mass: 376.13694696 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.24
• 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	+	0.6800	68.00%
Caco-2	-	0.8660	86.60%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6031	60.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7668	76.68%
OATP1B3 inhibitior	+	0.9559	95.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9399	93.99%
P-glycoprotein inhibitior	-	0.8804	88.04%
P-glycoprotein substrate	-	0.7858	78.58%
CYP3A4 substrate	+	0.5384	53.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8775	87.75%
CYP3A4 inhibition	-	0.8822	88.22%
CYP2C9 inhibition	-	0.9094	90.94%
CYP2C19 inhibition	-	0.8779	87.79%
CYP2D6 inhibition	-	0.8794	87.94%
CYP1A2 inhibition	-	0.8460	84.60%
CYP2C8 inhibition	-	0.8264	82.64%
CYP inhibitory promiscuity	-	0.7701	77.01%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6562	65.62%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9609	96.09%
Skin irritation	-	0.7440	74.40%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5273	52.73%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6773	67.73%
skin sensitisation	-	0.8705	87.05%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.4553	45.53%
Acute Oral Toxicity (c)	III	0.4925	49.25%
Estrogen receptor binding	+	0.5361	53.61%
Androgen receptor binding	+	0.5221	52.21%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5970	59.70%
Aromatase binding	+	0.5615	56.15%
PPAR gamma	-	0.5300	53.00%
Honey bee toxicity	-	0.7993	79.93%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.3638	36.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.19%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.12%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.55%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.17%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.07%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.64%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.12%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	81.37%	92.50%

Plants that contains it

• Phlomoides rotata

Cross-Links

• PubChem: 163024778
• LOTUS: LTS0086549
• wikiData: Q105186168