methyl 5,6-dihydroxy-7-methylidene-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: e44b861d-f53d-4234-a2e6-feb1bbbbddee
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: methyl 5,6-dihydroxy-7-methylidene-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C(C(C2=C)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=COC(C2C1C(C(C2=C)O)O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C17H24O11/c1-5-8-9(12(21)10(5)19)6(15(24)25-2)4-26-16(8)28-17-14(23)13(22)11(20)7(3-18)27-17/h4,7-14,16-23H,1,3H2,2H3
• InChI Key: QUTNKSUGCORXII-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.26
• H-Bond Acceptor: 11
• 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	+	0.5723	57.23%
Caco-2	-	0.8797	87.97%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6451	64.51%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.7242	72.42%
OATP1B3 inhibitior	+	0.9641	96.41%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9414	94.14%
P-glycoprotein inhibitior	-	0.8427	84.27%
P-glycoprotein substrate	-	0.8318	83.18%
CYP3A4 substrate	+	0.5853	58.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	-	0.8668	86.68%
CYP2C9 inhibition	-	0.8954	89.54%
CYP2C19 inhibition	-	0.8293	82.93%
CYP2D6 inhibition	-	0.9089	90.89%
CYP1A2 inhibition	-	0.8824	88.24%
CYP2C8 inhibition	-	0.6708	67.08%
CYP inhibitory promiscuity	-	0.7168	71.68%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7199	71.99%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9079	90.79%
Skin irritation	-	0.7788	77.88%
Skin corrosion	-	0.9493	94.93%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5698	56.98%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8576	85.76%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.7156	71.56%
Acute Oral Toxicity (c)	III	0.4897	48.97%
Estrogen receptor binding	+	0.6174	61.74%
Androgen receptor binding	-	0.5484	54.84%
Thyroid receptor binding	+	0.5209	52.09%
Glucocorticoid receptor binding	-	0.6127	61.27%
Aromatase binding	+	0.5964	59.64%
PPAR gamma	-	0.5135	51.35%
Honey bee toxicity	-	0.8179	81.79%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.3948	39.48%

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	94.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.97%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.73%	94.73%
CHEMBL2581	P07339	Cathepsin D	86.21%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.13%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.64%	96.00%

Plants that contains it

• Alibertia edulis
• Zaluzianskya capensis

Cross-Links

• PubChem: 74368795
• LOTUS: LTS0050034
• wikiData: Q104196227