(1S)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6-tetrahydrocyclopenta[c]pyran-4,7-dicarboxylic acid

Details

• Internal ID: 6e237e42-5a4c-41c4-99cb-b34e02488739
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (1S)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6-tetrahydrocyclopenta[c]pyran-4,7-dicarboxylic acid
• SMILES (Canonical): C1CC(=C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)C(=O)O
• SMILES (Isomeric): C1CC(=C2C1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)C(=O)O
• InChI: InChI=1S/C16H20O11/c17-3-8-10(18)11(19)12(20)16(26-8)27-15-9-5(1-2-6(9)13(21)22)7(4-25-15)14(23)24/h4-5,8,10-12,15-20H,1-3H2,(H,21,22)(H,23,24)/t5?,8-,10-,11+,12-,15+,16+/m1/s1
• InChI Key: KBSHFBMEJDATRW-UJWGOUDUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₁₁
• Molecular Weight: 388.32 g/mol
• Exact Mass: 388.10056145 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.08
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4873	48.73%
Caco-2	-	0.9313	93.13%
Blood Brain Barrier	-	0.5803	58.03%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8082	80.82%
OATP2B1 inhibitior	-	0.7145	71.45%
OATP1B1 inhibitior	+	0.8279	82.79%
OATP1B3 inhibitior	+	0.9512	95.12%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8740	87.40%
P-glycoprotein inhibitior	-	0.9066	90.66%
P-glycoprotein substrate	-	0.9215	92.15%
CYP3A4 substrate	+	0.5235	52.35%
CYP2C9 substrate	-	0.6093	60.93%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.9182	91.82%
CYP2C9 inhibition	-	0.8301	83.01%
CYP2C19 inhibition	-	0.8666	86.66%
CYP2D6 inhibition	-	0.8877	88.77%
CYP1A2 inhibition	-	0.8196	81.96%
CYP2C8 inhibition	-	0.6423	64.23%
CYP inhibitory promiscuity	-	0.8638	86.38%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6703	67.03%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.8256	82.56%
Skin irritation	-	0.7466	74.66%
Skin corrosion	-	0.9409	94.09%
Ames mutagenesis	-	0.5840	58.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.6714	67.14%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	-	0.7464	74.64%
skin sensitisation	-	0.8799	87.99%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6233	62.33%
Acute Oral Toxicity (c)	III	0.4365	43.65%
Estrogen receptor binding	+	0.6339	63.39%
Androgen receptor binding	+	0.5679	56.79%
Thyroid receptor binding	-	0.5492	54.92%
Glucocorticoid receptor binding	-	0.5751	57.51%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5540	55.40%
Honey bee toxicity	-	0.8838	88.38%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.4199	41.99%

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	96.02%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	93.92%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.15%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.30%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.38%	99.17%
CHEMBL2581	P07339	Cathepsin D	83.62%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.38%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	83.25%	92.50%

Plants that contains it

• Erinus alpinus

Cross-Links

• PubChem: 101743543
• NPASS: NPC226016