[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 19aa3e6c-8485-46c5-85f3-e8f51318a46b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC(=O)OC2CC(C3C2C=COC3OC4C(C(C(C(O4)CO)O)O)O)(CO)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C(=O)O[C@@H]2C[C@]([C@@H]3[C@H]2C=CO[C@H]3O[C@H]4[C@H](C([C@H](C(O4)CO)O)O)O)(CO)O)O
• InChI: InChI=1S/C25H32O13/c1-34-15-4-2-12(8-14(15)28)3-5-18(29)36-16-9-25(33,11-27)19-13(16)6-7-35-23(19)38-24-22(32)21(31)20(30)17(10-26)37-24/h2-8,13,16-17,19-24,26-28,30-33H,9-11H2,1H3/b5-3+/t13-,16+,17?,19+,20-,21?,22-,23-,24-,25+/m0/s1
• InChI Key: AOYKWOOKYIPTGP-SUNGHJAISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₃
• Molecular Weight: 540.50 g/mol
• Exact Mass: 540.18429107 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.63
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6724	67.24%
Caco-2	-	0.8949	89.49%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5048	50.48%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8598	85.98%
OATP1B3 inhibitior	+	0.9705	97.05%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5616	56.16%
P-glycoprotein inhibitior	-	0.6158	61.58%
P-glycoprotein substrate	-	0.5390	53.90%
CYP3A4 substrate	+	0.6910	69.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8588	85.88%
CYP3A4 inhibition	-	0.9050	90.50%
CYP2C9 inhibition	-	0.9241	92.41%
CYP2C19 inhibition	-	0.8079	80.79%
CYP2D6 inhibition	-	0.8645	86.45%
CYP1A2 inhibition	-	0.8685	86.85%
CYP2C8 inhibition	+	0.7253	72.53%
CYP inhibitory promiscuity	-	0.8220	82.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5591	55.91%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9462	94.62%
Skin irritation	-	0.7865	78.65%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7876	78.76%
Micronuclear	+	0.5133	51.33%
Hepatotoxicity	-	0.8194	81.94%
skin sensitisation	-	0.8157	81.57%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8821	88.21%
Acute Oral Toxicity (c)	III	0.6366	63.66%
Estrogen receptor binding	+	0.7798	77.98%
Androgen receptor binding	-	0.5223	52.23%
Thyroid receptor binding	+	0.5276	52.76%
Glucocorticoid receptor binding	+	0.5421	54.21%
Aromatase binding	+	0.6481	64.81%
PPAR gamma	+	0.7129	71.29%
Honey bee toxicity	-	0.7574	75.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.4129	41.29%

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	99.63%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.10%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.96%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.12%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.66%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.11%	89.00%
CHEMBL4208	P20618	Proteasome component C5	92.36%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.24%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.77%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.03%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.62%	95.89%
CHEMBL3194	P02766	Transthyretin	86.17%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.43%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.33%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.43%	95.89%
CHEMBL4302	P08183	P-glycoprotein 1	83.33%	92.98%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.66%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.63%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.21%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	82.12%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.43%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.13%	86.92%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.43%	97.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.01%	96.21%

Plants that contains it

• Catalpa ovata

Cross-Links

• PubChem: 162875622
• LOTUS: LTS0040530
• wikiData: Q104916068