Dimethyl 5,6-dihydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4,7-dicarboxylate

Details

• Internal ID: 9993f58e-b73a-4755-a880-3f4d0adf9939
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: dimethyl 5,6-dihydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4,7-dicarboxylate
• SMILES (Canonical): COC(=O)C1C2C(C(C1O)O)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC
• SMILES (Isomeric): COC(=O)C1C2C(C(C1O)O)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC
• InChI: InChI=1S/C18H26O13/c1-27-15(25)5-4-29-17(8-7(5)11(21)12(22)9(8)16(26)28-2)31-18-14(24)13(23)10(20)6(3-19)30-18/h4,6-14,17-24H,3H2,1-2H3
• InChI Key: BSLDUMMCFUUGHA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₁₃
• Molecular Weight: 450.40 g/mol
• Exact Mass: 450.13734088 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -4.03
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4811	48.11%
Caco-2	-	0.8715	87.15%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6932	69.32%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.6962	69.62%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8235	82.35%
P-glycoprotein inhibitior	-	0.7419	74.19%
P-glycoprotein substrate	-	0.7678	76.78%
CYP3A4 substrate	+	0.5988	59.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8781	87.81%
CYP3A4 inhibition	-	0.8782	87.82%
CYP2C9 inhibition	-	0.8919	89.19%
CYP2C19 inhibition	-	0.8871	88.71%
CYP2D6 inhibition	-	0.9130	91.30%
CYP1A2 inhibition	-	0.9162	91.62%
CYP2C8 inhibition	-	0.6457	64.57%
CYP inhibitory promiscuity	-	0.7997	79.97%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6930	69.30%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9323	93.23%
Skin irritation	-	0.7782	77.82%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5154	51.54%
Micronuclear	-	0.5741	57.41%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8848	88.48%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.7638	76.38%
Acute Oral Toxicity (c)	III	0.4986	49.86%
Estrogen receptor binding	+	0.6609	66.09%
Androgen receptor binding	-	0.5668	56.68%
Thyroid receptor binding	-	0.5754	57.54%
Glucocorticoid receptor binding	-	0.6453	64.53%
Aromatase binding	-	0.5923	59.23%
PPAR gamma	-	0.6501	65.01%
Honey bee toxicity	-	0.8263	82.63%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.4384	43.84%

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	95.89%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.29%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.13%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.89%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.75%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.72%	86.33%
CHEMBL2581	P07339	Cathepsin D	80.48%	98.95%

Plants that contains it

• Myxopyrum smilacifolium

Cross-Links

• PubChem: 75111193
• LOTUS: LTS0254108
• wikiData: Q104945289