2-[(17S,18S,19S,20R)-17-acetyloxy-20-[(2S,3S,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-carboxy-18,19,21-trihydroxy-16-methylhenicosyl]-6-hydroxybenzoic acid

Details

• Internal ID: b4c89bce-5052-471d-b083-894763ad5abd
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: 2-[(17S,18S,19S,20R)-17-acetyloxy-20-[(2S,3S,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-carboxy-18,19,21-trihydroxy-16-methylhenicosyl]-6-hydroxybenzoic acid
• SMILES (Canonical): CC(CCCCCCCCCCCCCCCC1=C(C(=CC=C1)O)C(=O)O)C(C(C(C(CO)OC2C(C(C(C(O2)CO)O)O)OC(=O)C)O)O)(C(=O)O)OC(=O)C
• SMILES (Isomeric): CC(CCCCCCCCCCCCCCCC1=C(C(=CC=C1)O)C(=O)O)[C@]([C@H]([C@@H]([C@@H](CO)O[C@H]2[C@H]([C@H]([C@@H]([C@H](O2)CO)O)O)OC(=O)C)O)O)(C(=O)O)OC(=O)C
• InChI: InChI=1S/C40H64O17/c1-24(18-15-13-11-9-7-5-4-6-8-10-12-14-16-19-27-20-17-21-28(45)31(27)37(50)51)40(39(52)53,57-26(3)44)36(49)33(47)30(23-42)56-38-35(54-25(2)43)34(48)32(46)29(22-41)55-38/h17,20-21,24,29-30,32-36,38,41-42,45-49H,4-16,18-19,22-23H2,1-3H3,(H,50,51)(H,52,53)/t24?,29-,30-,32-,33-,34+,35+,36+,38+,40+/m1/s1
• InChI Key: BRQJNWFMGNHEQO-LYJPMCOASA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₄O₁₇
• Molecular Weight: 816.90 g/mol
• Exact Mass: 816.41435057 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 28

Synonyms

• 2-[(17S,18S,19S,20R)-17-acetyloxy-20-[(2S,3S,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-carboxy-18,19,21-trihydroxy-16-methylhenicosyl]-6-hydroxybenzoic acid
• DTXSID90936304
• 2-O-Acetyl-5-O-(2-O-acetylhexopyranosyl)-2-C-[17-(2-carboxy-3-hydroxyphenyl)heptadecan-2-yl]hexonic acid
• D-Mannonic acid, 5-O-(2-O-acetyl-beta-D-mannopyranosyl)-, 16-(2-carboxy-3-hydroxyphenyl)-1-methylhexadecyl ester, 2-acetate, (R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5489	54.89%
Caco-2	-	0.8608	86.08%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8674	86.74%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	+	0.8485	84.85%
OATP1B3 inhibitior	+	0.8321	83.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6929	69.29%
P-glycoprotein inhibitior	+	0.7382	73.82%
P-glycoprotein substrate	+	0.6112	61.12%
CYP3A4 substrate	+	0.7000	70.00%
CYP2C9 substrate	-	0.8029	80.29%
CYP2D6 substrate	-	0.8843	88.43%
CYP3A4 inhibition	-	0.7446	74.46%
CYP2C9 inhibition	-	0.7740	77.40%
CYP2C19 inhibition	-	0.8282	82.82%
CYP2D6 inhibition	-	0.9495	94.95%
CYP1A2 inhibition	-	0.6821	68.21%
CYP2C8 inhibition	+	0.5095	50.95%
CYP inhibitory promiscuity	-	0.9397	93.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7065	70.65%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9032	90.32%
Skin irritation	-	0.8042	80.42%
Skin corrosion	-	0.9652	96.52%
Ames mutagenesis	-	0.6160	61.60%
Human Ether-a-go-go-Related Gene inhibition	+	0.6754	67.54%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6020	60.20%
Acute Oral Toxicity (c)	III	0.5748	57.48%
Estrogen receptor binding	+	0.7849	78.49%
Androgen receptor binding	+	0.6890	68.90%
Thyroid receptor binding	-	0.5388	53.88%
Glucocorticoid receptor binding	+	0.6545	65.45%
Aromatase binding	+	0.6717	67.17%
PPAR gamma	+	0.7034	70.34%
Honey bee toxicity	-	0.7470	74.70%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7476	74.76%
Fish aquatic toxicity	+	0.9732	97.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.20%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.57%	91.11%
CHEMBL1914	P06276	Butyrylcholinesterase	98.43%	95.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.09%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	97.10%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.27%	93.56%
CHEMBL2996	Q05655	Protein kinase C delta	92.66%	97.79%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	92.09%	94.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.03%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.73%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.75%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.60%	86.33%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	88.20%	97.29%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	87.93%	96.37%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.16%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.05%	96.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.88%	94.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.58%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.00%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.08%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.62%	95.50%

Plants that contains it

• Medicago arabica

Cross-Links

• PubChem: 197691
• LOTUS: LTS0268684
• wikiData: Q105168217