methyl (1S,4aS,6S,7R,7aS)-6-[(E,6S)-8-hydroxy-2,6-dimethyloct-2-enoyl]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: fe005a64-eb83-4b3c-b2e8-f422e05249a5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,6S,7R,7aS)-6-[(E,6S)-8-hydroxy-2,6-dimethyloct-2-enoyl]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)CCO)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@H](C)CCO)/C
• InChI: InChI=1S/C27H42O12/c1-13(8-9-28)6-5-7-14(2)24(33)37-18-10-16-17(25(34)35-4)12-36-26(20(16)15(18)3)39-27-23(32)22(31)21(30)19(11-29)38-27/h7,12-13,15-16,18-23,26-32H,5-6,8-11H2,1-4H3/b14-7+/t13-,15-,16+,18-,19+,20+,21+,22-,23+,26-,27-/m0/s1
• InChI Key: GUUVNQSNUOVRLG-RMQGLKJSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₂O₁₂
• Molecular Weight: 558.60 g/mol
• Exact Mass: 558.26762677 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6188	61.88%
Caco-2	-	0.8564	85.64%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7595	75.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6881	68.81%
OATP1B3 inhibitior	+	0.9278	92.78%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.5659	56.59%
P-glycoprotein inhibitior	-	0.4435	44.35%
P-glycoprotein substrate	+	0.5917	59.17%
CYP3A4 substrate	+	0.6842	68.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8792	87.92%
CYP3A4 inhibition	-	0.8387	83.87%
CYP2C9 inhibition	-	0.9285	92.85%
CYP2C19 inhibition	-	0.9017	90.17%
CYP2D6 inhibition	-	0.9369	93.69%
CYP1A2 inhibition	-	0.8549	85.49%
CYP2C8 inhibition	+	0.4735	47.35%
CYP inhibitory promiscuity	-	0.9702	97.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6973	69.73%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9357	93.57%
Skin irritation	-	0.6433	64.33%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6893	68.93%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6792	67.92%
skin sensitisation	-	0.9228	92.28%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6708	67.08%
Acute Oral Toxicity (c)	III	0.3950	39.50%
Estrogen receptor binding	+	0.7478	74.78%
Androgen receptor binding	+	0.5367	53.67%
Thyroid receptor binding	-	0.6200	62.00%
Glucocorticoid receptor binding	+	0.5795	57.95%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6096	60.96%
Honey bee toxicity	-	0.7166	71.66%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.8983	89.83%

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	98.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.75%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.26%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.18%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.64%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.10%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.24%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	86.96%	90.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.70%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.74%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	84.47%	92.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.62%	93.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.57%	94.08%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.38%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.68%	97.25%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.50%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.44%	94.45%

Plants that contains it

• Picconia excelsa

Cross-Links

• PubChem: 162855277
• LOTUS: LTS0018735
• wikiData: Q105020588