Methyl 7-(acetyloxymethyl)-5-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 8a8296d9-13b4-4dd8-a8fa-c02c8ce205dd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 7-(acetyloxymethyl)-5-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC(=O)OCC1=CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC(=O)OCC1=CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O
• InChI: InChI=1S/C19H26O12/c1-7(21)28-5-8-3-10(22)13-9(17(26)27-2)6-29-18(12(8)13)31-19-16(25)15(24)14(23)11(4-20)30-19/h3,6,10-16,18-20,22-25H,4-5H2,1-2H3
• InChI Key: YSOBQIMODQOGKQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₁₂
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.14242626 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• FT-0775410

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4645	46.45%
Caco-2	-	0.8728	87.28%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6675	66.75%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.7622	76.22%
OATP1B3 inhibitior	+	0.9588	95.88%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6713	67.13%
P-glycoprotein inhibitior	-	0.7917	79.17%
P-glycoprotein substrate	-	0.7787	77.87%
CYP3A4 substrate	+	0.6120	61.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8891	88.91%
CYP3A4 inhibition	-	0.9446	94.46%
CYP2C9 inhibition	-	0.9135	91.35%
CYP2C19 inhibition	-	0.8826	88.26%
CYP2D6 inhibition	-	0.9131	91.31%
CYP1A2 inhibition	-	0.9037	90.37%
CYP2C8 inhibition	-	0.6025	60.25%
CYP inhibitory promiscuity	-	0.8473	84.73%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7342	73.42%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9383	93.83%
Skin irritation	-	0.7743	77.43%
Skin corrosion	-	0.9486	94.86%
Ames mutagenesis	-	0.6037	60.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4515	45.15%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8833	88.33%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.8718	87.18%
Acute Oral Toxicity (c)	III	0.5019	50.19%
Estrogen receptor binding	+	0.6947	69.47%
Androgen receptor binding	+	0.5243	52.43%
Thyroid receptor binding	-	0.6031	60.31%
Glucocorticoid receptor binding	-	0.6260	62.60%
Aromatase binding	+	0.5235	52.35%
PPAR gamma	-	0.4879	48.79%
Honey bee toxicity	-	0.7747	77.47%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.6722	67.22%

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	96.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.32%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.29%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.26%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	91.60%	94.73%
CHEMBL2581	P07339	Cathepsin D	81.66%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.45%	86.33%

Plants that contains it

• Daphniphyllum macropodum
• Galium mollugo
• Globularia bisnagarica
• Lamium amplexicaule
• Oldenlandia herbacea var. herbacea
• Paederia foetida
• Spermacoce verticillata
• Trichotosia latifolia

Cross-Links

• PubChem: 12309039
• LOTUS: LTS0117888
• wikiData: Q105360343