(4S,5E,6S)-5-(2-hydroxyethylidene)-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid

Details

• Internal ID: ff84e6df-520f-47a8-a9bd-39d5139c113b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (4S,5E,6S)-5-(2-hydroxyethylidene)-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid
• SMILES (Canonical): C1=CC(=CC=C1CCOC(=O)CC2C(=COC(C2=CCO)OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CCOC(=O)C[C@@H]\2C(=CO[C@H](/C2=C/CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)O
• InChI: InChI=1S/C24H30O13/c25-7-5-14-15(9-18(28)34-8-6-12-1-3-13(27)4-2-12)16(22(32)33)11-35-23(14)37-24-21(31)20(30)19(29)17(10-26)36-24/h1-5,11,15,17,19-21,23-27,29-31H,6-10H2,(H,32,33)/b14-5+/t15-,17+,19+,20-,21+,23-,24-/m0/s1
• InChI Key: JORLYMGTWNNOMY-UWOKVVLSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₁₃
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.16864101 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.46
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7487	74.87%
Caco-2	-	0.9215	92.15%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8287	82.87%
OATP2B1 inhibitior	-	0.8494	84.94%
OATP1B1 inhibitior	+	0.7502	75.02%
OATP1B3 inhibitior	+	0.9349	93.49%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6072	60.72%
P-glycoprotein inhibitior	-	0.5659	56.59%
P-glycoprotein substrate	-	0.6276	62.76%
CYP3A4 substrate	+	0.6393	63.93%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8717	87.17%
CYP3A4 inhibition	-	0.8875	88.75%
CYP2C9 inhibition	-	0.8226	82.26%
CYP2C19 inhibition	-	0.7394	73.94%
CYP2D6 inhibition	-	0.8955	89.55%
CYP1A2 inhibition	-	0.8315	83.15%
CYP2C8 inhibition	+	0.7889	78.89%
CYP inhibitory promiscuity	-	0.8865	88.65%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6794	67.94%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9117	91.17%
Skin irritation	-	0.8290	82.90%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.5693	56.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.4260	42.60%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8437	84.37%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7960	79.60%
Acute Oral Toxicity (c)	III	0.5518	55.18%
Estrogen receptor binding	+	0.8011	80.11%
Androgen receptor binding	+	0.6607	66.07%
Thyroid receptor binding	-	0.5112	51.12%
Glucocorticoid receptor binding	+	0.5723	57.23%
Aromatase binding	+	0.5432	54.32%
PPAR gamma	+	0.6612	66.12%
Honey bee toxicity	-	0.7071	70.71%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9265	92.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	98.27%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.57%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.00%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.97%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.36%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.23%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.92%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.17%	94.45%
CHEMBL3194	P02766	Transthyretin	89.23%	90.71%
CHEMBL2581	P07339	Cathepsin D	87.39%	98.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.49%	83.57%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	85.66%	94.97%
CHEMBL3891	P07384	Calpain 1	85.42%	93.04%
CHEMBL3401	O75469	Pregnane X receptor	84.13%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.47%	93.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.92%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.80%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.89%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.13%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.97%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.28%	95.89%

Plants that contains it

• Fraxinus uhdei

Cross-Links

• PubChem: 101922701
• LOTUS: LTS0065458
• wikiData: Q105132498