(4S,5Z,6S)-4-[2-[[(1R,2S,3S,5S)-5-(1,3-dihydroxypropan-2-yl)-3-hydroxy-2-methylcyclopentyl]methoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid

Details

• Internal ID: 442ad701-e691-4449-8119-319ccfdfde61
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (4S,5Z,6S)-4-[2-[[(1R,2S,3S,5S)-5-(1,3-dihydroxypropan-2-yl)-3-hydroxy-2-methylcyclopentyl]methoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)CC(=O)OCC3C(C(CC3C(CO)CO)O)C
• SMILES (Isomeric): C/C=C\1/[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)O)CC(=O)OC[C@H]3[C@@H]([C@H](C[C@@H]3C(CO)CO)O)C
• InChI: InChI=1S/C26H40O14/c1-3-13-15(5-20(31)37-9-16-11(2)18(30)4-14(16)12(6-27)7-28)17(24(35)36)10-38-25(13)40-26-23(34)22(33)21(32)19(8-29)39-26/h3,10-12,14-16,18-19,21-23,25-30,32-34H,4-9H2,1-2H3,(H,35,36)/b13-3-/t11-,14+,15-,16-,18-,19+,21+,22-,23+,25-,26-/m0/s1
• InChI Key: YKOPVYGFHABLIS-WKHRVAGJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₁₄
• Molecular Weight: 576.60 g/mol
• Exact Mass: 576.24180595 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.14
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6696	66.96%
Caco-2	-	0.8946	89.46%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8276	82.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3217	32.17%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5320	53.20%
P-glycoprotein inhibitior	-	0.6039	60.39%
P-glycoprotein substrate	-	0.5065	50.65%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8907	89.07%
CYP3A4 inhibition	-	0.8732	87.32%
CYP2C9 inhibition	-	0.9140	91.40%
CYP2C19 inhibition	-	0.9022	90.22%
CYP2D6 inhibition	-	0.9148	91.48%
CYP1A2 inhibition	-	0.9062	90.62%
CYP2C8 inhibition	+	0.5087	50.87%
CYP inhibitory promiscuity	-	0.9461	94.61%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7635	76.35%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9223	92.23%
Skin irritation	-	0.7548	75.48%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.5077	50.77%
Human Ether-a-go-go-Related Gene inhibition	+	0.6870	68.70%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7727	77.27%
skin sensitisation	-	0.8981	89.81%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8082	80.82%
Acute Oral Toxicity (c)	III	0.5366	53.66%
Estrogen receptor binding	+	0.7850	78.50%
Androgen receptor binding	+	0.5834	58.34%
Thyroid receptor binding	-	0.5970	59.70%
Glucocorticoid receptor binding	+	0.6018	60.18%
Aromatase binding	+	0.5765	57.65%
PPAR gamma	+	0.6033	60.33%
Honey bee toxicity	-	0.7218	72.18%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9166	91.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.75%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.79%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	89.85%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.43%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.35%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.95%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.31%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	86.47%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.34%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	86.02%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.75%	99.17%
CHEMBL2581	P07339	Cathepsin D	85.49%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.26%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	84.75%	91.49%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	84.08%	80.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.79%	93.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.99%	86.92%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.25%	94.80%

Plants that contains it

• Jasminum mesnyi

Cross-Links

• PubChem: 162906416
• LOTUS: LTS0107379
• wikiData: Q105349807