[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-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: 9cd0b64f-0e58-4a82-8868-885014928b9f
• 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)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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)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)O)O
• InChI: InChI=1S/C27H34O14/c1-12-11-37-26(9-15(12)38-22(33)13-5-3-2-4-6-13)25(35)27(36)17(29)7-14(8-18(27)41-26)23(34)40-24-21(32)20(31)19(30)16(10-28)39-24/h2-6,12,14-21,24,28-32,36H,7-11H2,1H3/t12-,14+,15+,16-,17+,18-,19-,20+,21-,24+,26+,27-/m1/s1
• InChI Key: VWVDXHBJGQKCJA-PAMCWREESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₄
• Molecular Weight: 582.50 g/mol
• Exact Mass: 582.19485575 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.22
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6185	61.85%
Caco-2	-	0.8905	89.05%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6979	69.79%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.8478	84.78%
OATP1B3 inhibitior	+	0.9617	96.17%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6431	64.31%
P-glycoprotein inhibitior	-	0.4695	46.95%
P-glycoprotein substrate	+	0.5309	53.09%
CYP3A4 substrate	+	0.7057	70.57%
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	+	0.5601	56.01%
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	-	0.9354	93.54%
Skin irritation	-	0.7715	77.15%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7220	72.20%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5841	58.41%
skin sensitisation	-	0.9160	91.60%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4068	40.68%
Estrogen receptor binding	+	0.8238	82.38%
Androgen receptor binding	+	0.7010	70.10%
Thyroid receptor binding	-	0.5278	52.78%
Glucocorticoid receptor binding	+	0.6452	64.52%
Aromatase binding	+	0.6299	62.99%
PPAR gamma	+	0.6369	63.69%
Honey bee toxicity	-	0.7105	71.05%
Biodegradation	-	0.7250	72.50%
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	96.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.11%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.04%	96.61%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	95.85%	94.23%
CHEMBL1951	P21397	Monoamine oxidase A	95.63%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	95.60%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.81%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.78%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.08%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.92%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.73%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.21%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.51%	94.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.03%	96.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.62%	94.97%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.57%	99.23%
CHEMBL5028	O14672	ADAM10	81.07%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.85%	91.19%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.39%	83.00%

Plants that contains it

• Phyllanthus emblica

Cross-Links

• PubChem: 10099785
• LOTUS: LTS0047569
• wikiData: Q105298292