Cyclopenta[c]pyran-4-carboxylic acid, 1,4a,5,7a-tetrahydro-5-hydroxy-1-[[6-O-[2-hydroxy-1-(hydroxymethyl)ethyl]-beta-D-glucopyranosyl]oxy]-7-(hydroxymethyl)-, methyl ester, (1S,4aS,5R,7aS)-

Details

• Internal ID: e441b091-5b76-4535-a975-ce41910c44d0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5R,7aS)-1-[(2S,3R,4S,5S,6R)-6-(1,3-dihydroxypropan-2-yloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)COC(CO)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(CO)CO)O)O)O
• InChI: InChI=1S/C20H30O13/c1-29-18(28)10-6-31-19(13-8(3-21)2-11(24)14(10)13)33-20-17(27)16(26)15(25)12(32-20)7-30-9(4-22)5-23/h2,6,9,11-17,19-27H,3-5,7H2,1H3/t11-,12-,13-,14+,15-,16+,17-,19+,20+/m1/s1
• InChI Key: IITIMORRSOFNLI-NZRRXMJFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₁₃
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.16864101 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -4.80
• Atomic LogP (AlogP): -3.88
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

• 1253964-66-7
• Cyclopenta[c]pyran-4-carboxylic acid, 1,4a,5,7a-tetrahydro-5-hydroxy-1-[[6-O-[2-hydroxy-1-(hydroxymethyl)ethyl]-beta-D-glucopyranosyl]oxy]-7-(hydroxymethyl)-, methyl ester, (1S,4aS,5R,7aS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8940	89.40%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7080	70.80%
OATP2B1 inhibitior	-	0.8612	86.12%
OATP1B1 inhibitior	+	0.7954	79.54%
OATP1B3 inhibitior	+	0.9693	96.93%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7495	74.95%
P-glycoprotein inhibitior	-	0.7733	77.33%
P-glycoprotein substrate	-	0.6796	67.96%
CYP3A4 substrate	+	0.6147	61.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.9525	95.25%
CYP2C9 inhibition	-	0.9255	92.55%
CYP2C19 inhibition	-	0.8242	82.42%
CYP2D6 inhibition	-	0.9053	90.53%
CYP1A2 inhibition	-	0.8914	89.14%
CYP2C8 inhibition	-	0.6412	64.12%
CYP inhibitory promiscuity	-	0.7430	74.30%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6491	64.91%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.8014	80.14%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3674	36.74%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8832	88.32%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5739	57.39%
Acute Oral Toxicity (c)	III	0.4977	49.77%
Estrogen receptor binding	+	0.6457	64.57%
Androgen receptor binding	-	0.5106	51.06%
Thyroid receptor binding	-	0.6164	61.64%
Glucocorticoid receptor binding	-	0.6578	65.78%
Aromatase binding	+	0.5572	55.72%
PPAR gamma	-	0.5437	54.37%
Honey bee toxicity	-	0.8160	81.60%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	-	0.4150	41.50%

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	97.01%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.70%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.29%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.27%	99.17%
CHEMBL2581	P07339	Cathepsin D	85.06%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.04%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.98%	96.00%

Plants that contains it

• Spermacoce verticillata

Cross-Links

• PubChem: 102052890
• LOTUS: LTS0200046
• wikiData: Q105113742