methyl (1S,4aS,6S,7R,7aS)-6-[(2E)-6-hydroxy-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: 5350af78-31c6-47bc-bdb9-e450a0c93b47
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,6S,7R,7aS)-6-[(2E)-6-hydroxy-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)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/CCC(C)(C=C)O)/C
• InChI: InChI=1S/C27H40O12/c1-6-27(4,34)9-7-8-13(2)23(32)37-17-10-15-16(24(33)35-5)12-36-25(19(15)14(17)3)39-26-22(31)21(30)20(29)18(11-28)38-26/h6,8,12,14-15,17-22,25-26,28-31,34H,1,7,9-11H2,2-5H3/b13-8+/t14-,15+,17-,18+,19+,20+,21-,22+,25-,26-,27?/m0/s1
• InChI Key: AZMKRMKMLKONRC-HCLJLRJYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₁₂
• Molecular Weight: 556.60 g/mol
• Exact Mass: 556.25197671 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.06
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7085	70.85%
Caco-2	-	0.8503	85.03%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6630	66.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6883	68.83%
OATP1B3 inhibitior	+	0.8937	89.37%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7553	75.53%
BSEP inhibitior	+	0.7992	79.92%
P-glycoprotein inhibitior	+	0.5971	59.71%
P-glycoprotein substrate	-	0.5090	50.90%
CYP3A4 substrate	+	0.7002	70.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8824	88.24%
CYP3A4 inhibition	-	0.7770	77.70%
CYP2C9 inhibition	-	0.8621	86.21%
CYP2C19 inhibition	-	0.9085	90.85%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	-	0.8976	89.76%
CYP2C8 inhibition	+	0.6554	65.54%
CYP inhibitory promiscuity	-	0.9387	93.87%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6538	65.38%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9414	94.14%
Skin irritation	-	0.5270	52.70%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.4127	41.27%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6415	64.15%
skin sensitisation	-	0.8915	89.15%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6604	66.04%
Acute Oral Toxicity (c)	III	0.4965	49.65%
Estrogen receptor binding	+	0.7542	75.42%
Androgen receptor binding	+	0.5616	56.16%
Thyroid receptor binding	-	0.5630	56.30%
Glucocorticoid receptor binding	+	0.5504	55.04%
Aromatase binding	+	0.5289	52.89%
PPAR gamma	+	0.6869	68.69%
Honey bee toxicity	-	0.6838	68.38%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8339	83.39%

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	98.56%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	95.41%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.04%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.08%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.81%	99.17%
CHEMBL2581	P07339	Cathepsin D	88.53%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.32%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.97%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.33%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.25%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.01%	96.95%
CHEMBL5028	O14672	ADAM10	83.34%	97.50%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.91%	90.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.68%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.50%	96.90%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.29%	91.24%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.10%	97.36%
CHEMBL5255	O00206	Toll-like receptor 4	81.80%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.92%	91.07%

Plants that contains it

• Jasminum nervosum
• Picconia excelsa

Cross-Links

• PubChem: 101708185
• LOTUS: LTS0060276
• wikiData: Q104921793