methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: b6e7f515-0e31-41c2-9b63-e08d83568a57
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)COC(=O)C=CC4=CC=C(C=C4)O)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC=C(C=C4)O)O)O)O
• InChI: InChI=1S/C26H30O12/c1-34-24(33)17-11-36-25(20-14(10-27)5-8-16(17)20)38-26-23(32)22(31)21(30)18(37-26)12-35-19(29)9-4-13-2-6-15(28)7-3-13/h2-7,9,11,16,18,20-23,25-28,30-32H,8,10,12H2,1H3/b9-4+/t16-,18-,20-,21-,22+,23-,25+,26+/m1/s1
• InChI Key: IVYAOUHUAWZJDB-UZOBGTHZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₁₂
• Molecular Weight: 534.50 g/mol
• Exact Mass: 534.17372639 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.26
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• (1S)-1alpha-[6-O-[(E)-4-Hydroxycinnamoyl]-beta-D-glucopyranosyloxy]-7-(hydroxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6367	63.67%
Caco-2	-	0.8856	88.56%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7156	71.56%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8031	80.31%
OATP1B3 inhibitior	+	0.9711	97.11%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6928	69.28%
P-glycoprotein inhibitior	-	0.5535	55.35%
P-glycoprotein substrate	-	0.5682	56.82%
CYP3A4 substrate	+	0.6798	67.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.8916	89.16%
CYP2C9 inhibition	-	0.8823	88.23%
CYP2C19 inhibition	-	0.7339	73.39%
CYP2D6 inhibition	-	0.8899	88.99%
CYP1A2 inhibition	-	0.8398	83.98%
CYP2C8 inhibition	+	0.7545	75.45%
CYP inhibitory promiscuity	-	0.7701	77.01%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6237	62.37%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9375	93.75%
Skin irritation	-	0.8038	80.38%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.6037	60.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4259	42.59%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8391	83.91%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5950	59.50%
Acute Oral Toxicity (c)	III	0.5120	51.20%
Estrogen receptor binding	+	0.7902	79.02%
Androgen receptor binding	+	0.6760	67.60%
Thyroid receptor binding	-	0.5518	55.18%
Glucocorticoid receptor binding	+	0.6611	66.11%
Aromatase binding	-	0.5271	52.71%
PPAR gamma	+	0.6237	62.37%
Honey bee toxicity	-	0.7950	79.50%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9330	93.30%

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	98.39%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.98%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.03%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.90%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.87%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.61%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.09%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.64%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	87.48%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	87.35%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.18%	89.62%
CHEMBL4208	P20618	Proteasome component C5	85.38%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.85%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.82%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	84.74%	92.50%
CHEMBL2581	P07339	Cathepsin D	84.24%	98.95%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.08%	89.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.14%	95.89%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 44255238
• NPASS: NPC82182