Chrysogeside A

Details

• Internal ID: 3eb4f89a-e1f5-4b77-bae3-ae563e6021c9
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (E,2R)-2-hydroxy-N-[(2S,3R,4E,8Z)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexadeca-4,8-dien-2-yl]octadec-3-enamide
• SMILES (Canonical): CCCCCCCCCCCCCCC=CC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=CCCCCCCC)O)O
• SMILES (Isomeric): CCCCCCCCCCCCCC/C=C/[C@H](C(=O)N[C@@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)[C@@H](/C=C/CC/C=C\CCCCCCC)O)O
• InChI: InChI=1S/C40H73NO9/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-34(44)39(48)41-32(31-49-40-38(47)37(46)36(45)35(30-42)50-40)33(43)28-26-24-22-20-18-14-12-10-8-6-4-2/h18,20,26-29,32-38,40,42-47H,3-17,19,21-25,30-31H2,1-2H3,(H,41,48)/b20-18-,28-26+,29-27+/t32-,33+,34+,35+,36+,37-,38+,40+/m0/s1
• InChI Key: ZSSGCZVAMMVAPO-CTUXNYLFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₇₃NO₉
• Molecular Weight: 712.00 g/mol
• Exact Mass: 711.52853291 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 9.30
• Atomic LogP (AlogP): 5.91
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 31

Synonyms

• CHEBI:68069
• CHEMBL1802289
• DTXSID801317167
• Q27136562
• (2R,3E)-N-[(2S,3R,4E,8Z)-1-(beta-D-glucopyranosyloxy)-3-hydroxyhexadeca-4,8-dien-2-yl]-2-hydroxyoctadec-3-enamide
• 1283114-63-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5446	54.46%
Caco-2	-	0.8673	86.73%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7599	75.99%
OATP2B1 inhibitior	-	0.5707	57.07%
OATP1B1 inhibitior	+	0.8123	81.23%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7780	77.80%
P-glycoprotein inhibitior	+	0.6711	67.11%
P-glycoprotein substrate	-	0.7110	71.10%
CYP3A4 substrate	+	0.6321	63.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8690	86.90%
CYP3A4 inhibition	-	0.6831	68.31%
CYP2C9 inhibition	-	0.9257	92.57%
CYP2C19 inhibition	-	0.8752	87.52%
CYP2D6 inhibition	-	0.8066	80.66%
CYP1A2 inhibition	-	0.8743	87.43%
CYP2C8 inhibition	-	0.6352	63.52%
CYP inhibitory promiscuity	-	0.8687	86.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7098	70.98%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9157	91.57%
Skin irritation	-	0.7583	75.83%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6831	68.31%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.8518	85.18%
skin sensitisation	-	0.8789	87.89%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6204	62.04%
Acute Oral Toxicity (c)	III	0.6732	67.32%
Estrogen receptor binding	+	0.7907	79.07%
Androgen receptor binding	-	0.5625	56.25%
Thyroid receptor binding	-	0.6015	60.15%
Glucocorticoid receptor binding	-	0.5187	51.87%
Aromatase binding	+	0.5401	54.01%
PPAR gamma	+	0.6236	62.36%
Honey bee toxicity	-	0.8726	87.26%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5571	55.71%
Fish aquatic toxicity	-	0.4074	40.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.72%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.46%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.66%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.64%	92.86%
CHEMBL3359	P21462	Formyl peptide receptor 1	96.00%	93.56%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	95.79%	97.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.61%	91.11%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	92.25%	85.94%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.84%	92.08%
CHEMBL5255	O00206	Toll-like receptor 4	91.30%	92.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.76%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	89.84%	94.73%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.70%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.72%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.61%	91.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.29%	96.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.05%	82.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.27%	96.47%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.88%	100.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	85.71%	91.81%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.66%	89.34%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	85.32%	92.32%
CHEMBL230	P35354	Cyclooxygenase-2	84.10%	89.63%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.02%	96.61%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.24%	92.88%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.23%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.27%	91.19%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.00%	92.78%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	80.86%	95.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.62%	95.50%
CHEMBL2514	O95665	Neurotensin receptor 2	80.21%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	80.04%	97.47%
CHEMBL221	P23219	Cyclooxygenase-1	80.02%	90.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 53355808
• LOTUS: LTS0183351
• wikiData: Q27136562