methyl (1S,4aS,6S,7R,7aS)-6-[(2E,6R)-2,6-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyocta-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: 803bb625-8adc-49eb-a3ff-90e2ab154c09
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,6S,7R,7aS)-6-[(2E,6R)-2,6-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyocta-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)CO)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)O)O)O)/C
• InChI: InChI=1S/C33H50O17/c1-6-33(4,50-32-27(41)25(39)23(37)20(12-35)48-32)9-7-8-14(2)28(42)46-18-10-16-17(29(43)44-5)13-45-30(21(16)15(18)3)49-31-26(40)24(38)22(36)19(11-34)47-31/h6,8,13,15-16,18-27,30-32,34-41H,1,7,9-12H2,2-5H3/b14-8+/t15-,16+,18-,19+,20+,21+,22+,23+,24-,25-,26+,27+,30-,31-,32-,33-/m0/s1
• InChI Key: FRAOYZACGUFGBH-TYAOGKFTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₀O₁₇
• Molecular Weight: 718.70 g/mol
• Exact Mass: 718.30480012 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -2.11
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5578	55.78%
Caco-2	-	0.8710	87.10%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7135	71.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7011	70.11%
OATP1B3 inhibitior	+	0.8685	86.85%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	+	0.6990	69.90%
P-glycoprotein inhibitior	+	0.6973	69.73%
P-glycoprotein substrate	+	0.5420	54.20%
CYP3A4 substrate	+	0.7043	70.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8792	87.92%
CYP3A4 inhibition	-	0.9112	91.12%
CYP2C9 inhibition	-	0.8707	87.07%
CYP2C19 inhibition	-	0.8824	88.24%
CYP2D6 inhibition	-	0.9423	94.23%
CYP1A2 inhibition	-	0.8816	88.16%
CYP2C8 inhibition	+	0.6885	68.85%
CYP inhibitory promiscuity	-	0.9157	91.57%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6499	64.99%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9207	92.07%
Skin irritation	-	0.6140	61.40%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	+	0.5246	52.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7861	78.61%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5824	58.24%
skin sensitisation	-	0.8886	88.86%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4694	46.94%
Acute Oral Toxicity (c)	III	0.5233	52.33%
Estrogen receptor binding	+	0.7926	79.26%
Androgen receptor binding	+	0.6254	62.54%
Thyroid receptor binding	-	0.5481	54.81%
Glucocorticoid receptor binding	+	0.6423	64.23%
Aromatase binding	+	0.5430	54.30%
PPAR gamma	+	0.6891	68.91%
Honey bee toxicity	-	0.6540	65.40%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8564	85.64%

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	99.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.56%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.69%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.31%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.82%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.87%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.35%	86.92%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.58%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.99%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.79%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.69%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.26%	96.90%
CHEMBL5255	O00206	Toll-like receptor 4	82.03%	92.50%
CHEMBL5028	O14672	ADAM10	81.96%	97.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.84%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.46%	95.83%

Plants that contains it

• Jasminum nervosum

Cross-Links

• PubChem: 10259301
• LOTUS: LTS0254070
• wikiData: Q105000045