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

Details

• Internal ID: 7c4b61e4-16c3-4ee4-bfd7-946624461fde
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 7-(hydroxymethyl)-5-methoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): COC1C=C(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)CO
• SMILES (Isomeric): COC1C=C(C2C1C(=COC2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)CO
• InChI: InChI=1S/C17H24O11/c1-25-8-2-6(3-18)10-11(8)7(15(23)24)5-26-16(10)28-17-14(22)13(21)12(20)9(4-19)27-17/h2,5,8-14,16-22H,3-4H2,1H3,(H,23,24)/t8?,9-,10?,11?,12-,13+,14-,16?,17+/m1/s1
• InChI Key: UGWIKFJKKFUZBT-XMSKVFGSSA-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: -3.20
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5197	51.97%
Caco-2	-	0.8971	89.71%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6687	66.87%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.7383	73.83%
OATP1B3 inhibitior	+	0.9687	96.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8816	88.16%
P-glycoprotein inhibitior	-	0.8546	85.46%
P-glycoprotein substrate	-	0.8394	83.94%
CYP3A4 substrate	+	0.5341	53.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8784	87.84%
CYP3A4 inhibition	-	0.9584	95.84%
CYP2C9 inhibition	-	0.9103	91.03%
CYP2C19 inhibition	-	0.8324	83.24%
CYP2D6 inhibition	-	0.9035	90.35%
CYP1A2 inhibition	-	0.8940	89.40%
CYP2C8 inhibition	-	0.7695	76.95%
CYP inhibitory promiscuity	-	0.7100	71.00%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6732	67.32%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9115	91.15%
Skin irritation	-	0.8055	80.55%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5373	53.73%
Micronuclear	-	0.7241	72.41%
Hepatotoxicity	-	0.8089	80.89%
skin sensitisation	-	0.8843	88.43%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6456	64.56%
Acute Oral Toxicity (c)	III	0.4889	48.89%
Estrogen receptor binding	+	0.5756	57.56%
Androgen receptor binding	-	0.5186	51.86%
Thyroid receptor binding	+	0.5154	51.54%
Glucocorticoid receptor binding	-	0.5198	51.98%
Aromatase binding	+	0.5547	55.47%
PPAR gamma	-	0.5376	53.76%
Honey bee toxicity	-	0.8261	82.61%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.6246	62.46%

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	95.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.87%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	87.62%	94.73%
CHEMBL2581	P07339	Cathepsin D	86.13%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.15%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.70%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.03%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.82%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.15%	97.36%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.96%	95.71%

Plants that contains it

• Gelsemium elegans

Cross-Links

• PubChem: 6325623
• NPASS: NPC107751