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

Details

• Internal ID: 62826d17-2290-49cd-83ca-a21fd7fb8d77
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 4-methoxycarbonyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-7-carboxylic acid
• SMILES (Canonical): COC(=O)C1=COC(C2C1C=CC2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=COC(C2C1C=CC2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C17H22O11/c1-25-15(24)8-5-26-16(10-6(8)2-3-7(10)14(22)23)28-17-13(21)12(20)11(19)9(4-18)27-17/h2-3,5-7,9-13,16-21H,4H2,1H3,(H,22,23)/t6?,7?,9-,10?,11-,12+,13-,16?,17+/m1/s1
• InChI Key: QXLZMFXGMGPPHW-VZNPXCROSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₁₁
• Molecular Weight: 402.30 g/mol
• Exact Mass: 402.11621151 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -2.28
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4663	46.63%
Caco-2	-	0.9013	90.13%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6885	68.85%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.7451	74.51%
OATP1B3 inhibitior	+	0.9720	97.20%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9254	92.54%
P-glycoprotein inhibitior	-	0.8747	87.47%
P-glycoprotein substrate	-	0.8576	85.76%
CYP3A4 substrate	+	0.5733	57.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8771	87.71%
CYP3A4 inhibition	-	0.9257	92.57%
CYP2C9 inhibition	-	0.8764	87.64%
CYP2C19 inhibition	-	0.8738	87.38%
CYP2D6 inhibition	-	0.9216	92.16%
CYP1A2 inhibition	-	0.8968	89.68%
CYP2C8 inhibition	-	0.5959	59.59%
CYP inhibitory promiscuity	-	0.8032	80.32%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6664	66.64%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9351	93.51%
Skin irritation	-	0.7833	78.33%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7663	76.63%
Micronuclear	-	0.5941	59.41%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.5535	55.35%
Acute Oral Toxicity (c)	III	0.4853	48.53%
Estrogen receptor binding	-	0.4831	48.31%
Androgen receptor binding	-	0.5213	52.13%
Thyroid receptor binding	-	0.6280	62.80%
Glucocorticoid receptor binding	-	0.6441	64.41%
Aromatase binding	-	0.6275	62.75%
PPAR gamma	-	0.6121	61.21%
Honey bee toxicity	-	0.8938	89.38%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	-	0.4893	48.93%

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	96.36%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.36%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.30%	99.17%
CHEMBL2581	P07339	Cathepsin D	88.55%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.37%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.26%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.34%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.15%	86.33%
CHEMBL5028	O14672	ADAM10	80.25%	97.50%

Plants that contains it

• Dioecrescis erythroclada

Cross-Links

• PubChem: 101596912
• LOTUS: LTS0016869
• wikiData: Q104399662