[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] (2S,3aR,4S,4'S,5'R,6S,7aR)-4'-benzoyloxy-3a,4-dihydroxy-5'-methyl-3-oxospiro[5,6,7,7a-tetrahydro-4H-1-benzofuran-2,2'-oxane]-6-carboxylate

Details

• Internal ID: 4e8a536a-7e52-41bb-a576-8c8ce77fbb28
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] (2S,3aR,4S,4'S,5'R,6S,7aR)-4'-benzoyloxy-3a,4-dihydroxy-5'-methyl-3-oxospiro[5,6,7,7a-tetrahydro-4H-1-benzofuran-2,2'-oxane]-6-carboxylate
• SMILES (Canonical): CC1COC2(CC1OC(=O)C3=CC=CC=C3)C(=O)C4(C(CC(CC4O2)C(=O)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1CO[C@]2(C[C@@H]1OC(=O)C3=CC=CC=C3)C(=O)[C@]4([C@H](C[C@@H](C[C@H]4O2)C(=O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O
• InChI: InChI=1S/C33H44O19/c1-13-12-46-32(9-16(13)47-27(42)14-5-3-2-4-6-14)31(44)33(45)19(36)7-15(8-20(33)52-32)28(43)51-30-26(24(40)22(38)18(11-35)49-30)50-29-25(41)23(39)21(37)17(10-34)48-29/h2-6,13,15-26,29-30,34-41,45H,7-12H2,1H3/t13-,15+,16+,17-,18-,19+,20-,21-,22-,23+,24+,25-,26-,29+,30+,32+,33-/m1/s1
• InChI Key: RLZZBHBWPWGOSA-WKLGMTJKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₁₉
• Molecular Weight: 744.70 g/mol
• Exact Mass: 744.24767917 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -4.40
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• [(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] (2S,3aR,4S,4'S,5'R,6S,7aR)-4'-benzoyloxy-3a,4-dihydroxy-5'-methyl-3-oxospiro[5,6,7,7a-tetrahydro-4H-1-benzofuran-2,2'-oxane]-6-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6185	61.85%
Caco-2	-	0.8866	88.66%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6979	69.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8430	84.30%
OATP1B3 inhibitior	+	0.9617	96.17%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.5753	57.53%
P-glycoprotein inhibitior	+	0.6743	67.43%
P-glycoprotein substrate	+	0.5933	59.33%
CYP3A4 substrate	+	0.7190	71.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8717	87.17%
CYP3A4 inhibition	-	0.9133	91.33%
CYP2C9 inhibition	-	0.9369	93.69%
CYP2C19 inhibition	-	0.8837	88.37%
CYP2D6 inhibition	-	0.9404	94.04%
CYP1A2 inhibition	-	0.9196	91.96%
CYP2C8 inhibition	+	0.5783	57.83%
CYP inhibitory promiscuity	-	0.9566	95.66%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9147	91.47%
Skin irritation	-	0.7715	77.15%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8008	80.08%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5932	59.32%
skin sensitisation	-	0.9160	91.60%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4728	47.28%
Acute Oral Toxicity (c)	III	0.4068	40.68%
Estrogen receptor binding	+	0.8064	80.64%
Androgen receptor binding	+	0.7105	71.05%
Thyroid receptor binding	-	0.5062	50.62%
Glucocorticoid receptor binding	+	0.6460	64.60%
Aromatase binding	+	0.5862	58.62%
PPAR gamma	+	0.6695	66.95%
Honey bee toxicity	-	0.6651	66.51%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9453	94.53%

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	97.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.51%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	96.27%	94.23%
CHEMBL1951	P21397	Monoamine oxidase A	96.18%	91.49%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.00%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.21%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	94.91%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.50%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.13%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.92%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.72%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.36%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.42%	97.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.38%	83.00%
CHEMBL5028	O14672	ADAM10	84.17%	97.50%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	84.08%	94.97%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.96%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.90%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	81.49%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.33%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.68%	99.23%

Plants that contains it

• Phyllanthus emblica

Cross-Links

• PubChem: 10417587
• LOTUS: LTS0168639
• wikiData: Q105240637