methyl (1S,4aS,6S,7R,7aS)-6-[(2E,6S)-6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2,6-dimethylocta-2,7-dienoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 27250240-e065-43fa-9774-eefc7f683aa5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,6S,7R,7aS)-6-[(2E,6S)-6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2,6-dimethylocta-2,7-dienoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C(=CCCC(C)(C=C)OC4C(C(C(C(O4)COC5C(C(CO5)(CO)O)O)O)O)O)C
• SMILES (Isomeric): C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)/C(=C/CC[C@@](C)(C=C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@](CO5)(CO)O)O)O)O)O)/C
• InChI: InChI=1S/C38H58O21/c1-6-37(4,59-35-29(46)27(44)25(42)22(57-35)13-53-36-30(47)38(50,14-40)15-54-36)9-7-8-16(2)31(48)55-20-10-18-19(32(49)51-5)12-52-33(23(18)17(20)3)58-34-28(45)26(43)24(41)21(11-39)56-34/h6,8,12,17-18,20-30,33-36,39-47,50H,1,7,9-11,13-15H2,2-5H3/b16-8+/t17-,18+,20-,21+,22+,23+,24+,25+,26-,27-,28+,29+,30-,33-,34-,35-,36+,37+,38+/m0/s1
• InChI Key: UQDJDIHBMNWWFP-PRPBYSKFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₈O₂₁
• Molecular Weight: 850.90 g/mol
• Exact Mass: 850.34705885 g/mol
• Topological Polar Surface Area (TPSA): 320.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -3.65
• H-Bond Acceptor: 21
• H-Bond Donor: 10
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7019	70.19%
Caco-2	-	0.8753	87.53%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7213	72.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7579	75.79%
OATP1B3 inhibitior	+	0.9005	90.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6271	62.71%
BSEP inhibitior	+	0.9195	91.95%
P-glycoprotein inhibitior	+	0.7341	73.41%
P-glycoprotein substrate	+	0.6964	69.64%
CYP3A4 substrate	+	0.7364	73.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8824	88.24%
CYP3A4 inhibition	-	0.8594	85.94%
CYP2C9 inhibition	-	0.8848	88.48%
CYP2C19 inhibition	-	0.9019	90.19%
CYP2D6 inhibition	-	0.9421	94.21%
CYP1A2 inhibition	-	0.9015	90.15%
CYP2C8 inhibition	+	0.7829	78.29%
CYP inhibitory promiscuity	-	0.9559	95.59%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5906	59.06%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9096	90.96%
Skin irritation	-	0.5368	53.68%
Skin corrosion	-	0.9314	93.14%
Ames mutagenesis	+	0.5646	56.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.8132	81.32%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5324	53.24%
skin sensitisation	-	0.8925	89.25%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6285	62.85%
Acute Oral Toxicity (c)	I	0.5636	56.36%
Estrogen receptor binding	+	0.8259	82.59%
Androgen receptor binding	+	0.6543	65.43%
Thyroid receptor binding	+	0.5281	52.81%
Glucocorticoid receptor binding	+	0.7279	72.79%
Aromatase binding	+	0.5708	57.08%
PPAR gamma	+	0.7911	79.11%
Honey bee toxicity	-	0.6285	62.85%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9005	90.05%

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	99.62%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.55%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.77%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	91.88%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.87%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	90.87%	94.73%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	89.98%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.62%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.06%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.82%	96.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.56%	98.75%
CHEMBL2581	P07339	Cathepsin D	87.39%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.20%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.88%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.78%	91.07%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.53%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.53%	94.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.43%	95.83%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.87%	95.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.76%	97.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.60%	97.36%
CHEMBL5255	O00206	Toll-like receptor 4	84.54%	92.50%
CHEMBL5028	O14672	ADAM10	83.78%	97.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.41%	97.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.97%	100.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.87%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.85%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.02%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.96%	99.23%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.48%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.07%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.63%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.14%	94.45%
CHEMBL5957	P21589	5'-nucleotidase	80.13%	97.78%

Plants that contains it

• Jasminum nervosum

Cross-Links

• PubChem: 10724247
• LOTUS: LTS0119687
• wikiData: Q105277171