[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl] 5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 4a715286-fe2e-4e58-9b46-56f2dd915f70
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1CC(C2C1COC=C2C(=O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC1CC(C2C1COC=C2C(=O)OC3C(C(C(C(O3)CO)O)O)O)O
• InChI: InChI=1S/C16H24O9/c1-6-2-9(18)11-7(6)4-23-5-8(11)15(22)25-16-14(21)13(20)12(19)10(3-17)24-16/h5-7,9-14,16-21H,2-4H2,1H3
• InChI Key: OQQDSUSKGYTVLM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₉
• Molecular Weight: 360.36 g/mol
• Exact Mass: 360.14203234 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.12
• H-Bond Acceptor: 9
• 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	+	0.7299	72.99%
Caco-2	-	0.8915	89.15%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6941	69.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8370	83.70%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9545	95.45%
P-glycoprotein inhibitior	-	0.8705	87.05%
P-glycoprotein substrate	-	0.7591	75.91%
CYP3A4 substrate	+	0.5779	57.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8544	85.44%
CYP3A4 inhibition	-	0.9505	95.05%
CYP2C9 inhibition	-	0.9416	94.16%
CYP2C19 inhibition	-	0.8741	87.41%
CYP2D6 inhibition	-	0.8960	89.60%
CYP1A2 inhibition	-	0.8596	85.96%
CYP2C8 inhibition	-	0.7248	72.48%
CYP inhibitory promiscuity	-	0.9174	91.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7243	72.43%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9442	94.42%
Skin irritation	-	0.7381	73.81%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	-	0.6532	65.32%
Human Ether-a-go-go-Related Gene inhibition	-	0.5349	53.49%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8977	89.77%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8715	87.15%
Acute Oral Toxicity (c)	III	0.4213	42.13%
Estrogen receptor binding	-	0.5235	52.35%
Androgen receptor binding	-	0.5132	51.32%
Thyroid receptor binding	-	0.5328	53.28%
Glucocorticoid receptor binding	-	0.6719	67.19%
Aromatase binding	-	0.5411	54.11%
PPAR gamma	-	0.6167	61.67%
Honey bee toxicity	-	0.7876	78.76%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9333	93.33%

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	97.71%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.28%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.42%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.97%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	86.21%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.78%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.51%	99.17%
CHEMBL2581	P07339	Cathepsin D	83.74%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.02%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.71%	97.36%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.05%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.96%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.10%	100.00%

Plants that contains it

• Penstemon virens

Cross-Links

• PubChem: 162989843
• LOTUS: LTS0259233
• wikiData: Q105197094