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

Details

• Internal ID: ac9ee230-70e7-4d4b-a12c-d374e99266bb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aS,5R,7aS)-7-(benzoyloxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl] (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C38H46O19/c39-11-17-6-7-19-21(15-52-36(25(17)19)57-38-32(47)30(45)28(43)24(13-41)55-38)34(49)53-22-10-18(14-51-33(48)16-4-2-1-3-5-16)26-20(22)8-9-50-35(26)56-37-31(46)29(44)27(42)23(12-40)54-37/h1-6,8-10,15,19-20,22-32,35-47H,7,11-14H2/t19-,20-,22+,23-,24-,25-,26-,27-,28-,29+,30+,31-,32-,35+,36+,37+,38+/m1/s1
• InChI Key: POILUOKEDPTHIF-PWNIDLQLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₆O₁₉
• Molecular Weight: 806.80 g/mol
• Exact Mass: 806.26332923 g/mol
• Topological Polar Surface Area (TPSA): 290.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -2.77
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5199	51.99%
Caco-2	-	0.8917	89.17%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7388	73.88%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8056	80.56%
OATP1B3 inhibitior	+	0.9628	96.28%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8211	82.11%
P-glycoprotein inhibitior	+	0.6765	67.65%
P-glycoprotein substrate	-	0.5507	55.07%
CYP3A4 substrate	+	0.6784	67.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8534	85.34%
CYP3A4 inhibition	-	0.8942	89.42%
CYP2C9 inhibition	-	0.8998	89.98%
CYP2C19 inhibition	-	0.7773	77.73%
CYP2D6 inhibition	-	0.9016	90.16%
CYP1A2 inhibition	-	0.8478	84.78%
CYP2C8 inhibition	+	0.7752	77.52%
CYP inhibitory promiscuity	-	0.8375	83.75%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6995	69.95%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9084	90.84%
Skin irritation	-	0.8097	80.97%
Skin corrosion	-	0.9611	96.11%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7467	74.67%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8621	86.21%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7294	72.94%
Acute Oral Toxicity (c)	III	0.4001	40.01%
Estrogen receptor binding	+	0.7955	79.55%
Androgen receptor binding	+	0.6921	69.21%
Thyroid receptor binding	+	0.5251	52.51%
Glucocorticoid receptor binding	-	0.5242	52.42%
Aromatase binding	-	0.5425	54.25%
PPAR gamma	+	0.7145	71.45%
Honey bee toxicity	-	0.7345	73.45%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9467	94.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.79%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.82%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.43%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.27%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.84%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.45%	99.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.03%	94.23%
CHEMBL3401	O75469	Pregnane X receptor	85.89%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.82%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	85.60%	94.45%
CHEMBL3891	P07384	Calpain 1	82.62%	93.04%
CHEMBL2581	P07339	Cathepsin D	82.04%	98.95%
CHEMBL5028	O14672	ADAM10	81.79%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.65%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	80.25%	90.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.08%	83.00%

Plants that contains it

• Globularia trichosantha

Cross-Links

• PubChem: 163067455
• LOTUS: LTS0176461
• wikiData: Q105212431