Bartoloside H

Details

• Internal ID: d7fd8bc5-5b8a-4c04-bf05-5eaa4a6755c7
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2S,3R,4S,5R)-2-[2-(6-chlorododecyl)-5-(6-chloropentadecyl)-3-hydroxyphenoxy]oxane-3,4,5-triol
• SMILES (Canonical): CCCCCCCCCC(CCCCCC1=CC(=C(C(=C1)OC2C(C(C(CO2)O)O)O)CCCCCC(CCCCCC)Cl)O)Cl
• SMILES (Isomeric): CCCCCCCCCC(CCCCCC1=CC(=C(C(=C1)O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)CCCCCC(CCCCCC)Cl)O)Cl
• InChI: InChI=1S/C38H66Cl2O6/c1-3-5-7-9-10-11-16-22-31(40)23-17-12-14-20-29-26-33(41)32(25-19-13-18-24-30(39)21-15-8-6-4-2)35(27-29)46-38-37(44)36(43)34(42)28-45-38/h26-27,30-31,34,36-38,41-44H,3-25,28H2,1-2H3/t30?,31?,34-,36+,37-,38+/m1/s1
• InChI Key: SNZCABRUTZVTFC-KJIMCQFPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₆Cl₂O₆
• Molecular Weight: 689.80 g/mol
• Exact Mass: 688.4236452 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: 12.30
• Atomic LogP (AlogP): 9.74
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 27

Synonyms

• (2S,3R,4S,5R)-2-[2-(6-chlorododecyl)-5-(6-chloropentadecyl)-3-hydroxyphenoxy]oxane-3,4,5-triol
• (2S,3R,4S,5R)-2-(2-(6-chlorododecyl)-5-(6-chloropentadecyl)-3-hydroxyphenoxy)oxane-3,4,5-triol
• RefChem:116597
• (2S,3R,4S,5R)-2-(2-(6-chlorododecyl)-5-(6-chloropentadecyl)-3-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol
• CHEMBL4065809
• CHEBI:205948
• DTXSID301334396
• 2-(6-Chlorododecyl)-5-(6-chloropentadecyl)-3-hydroxyphenyl beta-D-xylopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8340	83.40%
Caco-2	-	0.8338	83.38%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8059	80.59%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8619	86.19%
OATP1B3 inhibitior	+	0.8807	88.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8702	87.02%
P-glycoprotein inhibitior	+	0.6806	68.06%
P-glycoprotein substrate	+	0.5562	55.62%
CYP3A4 substrate	+	0.6848	68.48%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8012	80.12%
CYP3A4 inhibition	-	0.6256	62.56%
CYP2C9 inhibition	-	0.7654	76.54%
CYP2C19 inhibition	-	0.6630	66.30%
CYP2D6 inhibition	-	0.8648	86.48%
CYP1A2 inhibition	-	0.6082	60.82%
CYP2C8 inhibition	+	0.6814	68.14%
CYP inhibitory promiscuity	-	0.7097	70.97%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8287	82.87%
Carcinogenicity (trinary)	Non-required	0.7361	73.61%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9197	91.97%
Skin irritation	-	0.7360	73.60%
Skin corrosion	-	0.9237	92.37%
Ames mutagenesis	-	0.5932	59.32%
Human Ether-a-go-go-Related Gene inhibition	+	0.7882	78.82%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7165	71.65%
skin sensitisation	-	0.7497	74.97%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8751	87.51%
Acute Oral Toxicity (c)	III	0.5374	53.74%
Estrogen receptor binding	+	0.7514	75.14%
Androgen receptor binding	+	0.5998	59.98%
Thyroid receptor binding	-	0.5574	55.74%
Glucocorticoid receptor binding	-	0.5300	53.00%
Aromatase binding	+	0.5706	57.06%
PPAR gamma	+	0.6019	60.19%
Honey bee toxicity	-	0.8489	84.89%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6301	63.01%
Fish aquatic toxicity	+	0.9894	98.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.34%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.19%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	97.94%	89.63%
CHEMBL2581	P07339	Cathepsin D	97.79%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.82%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.69%	99.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	93.34%	92.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.34%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.93%	90.71%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	91.37%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.19%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.16%	94.73%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	89.11%	92.86%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.03%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.32%	96.95%
CHEMBL5805	Q9NR97	Toll-like receptor 8	87.22%	96.25%
CHEMBL240	Q12809	HERG	86.53%	89.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.17%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.08%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.00%	95.89%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	85.00%	92.32%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	84.59%	95.34%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.41%	96.90%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.00%	95.50%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.98%	97.29%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.86%	93.56%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.85%	91.81%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.33%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.56%	86.33%
CHEMBL4581	P52732	Kinesin-like protein 1	80.76%	93.18%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.21%	89.62%

Plants that contains it

• Beilschmiedia oligandra
• Endiandra introrsa

Cross-Links

• PubChem: 132582912
• LOTUS: LTS0006692
• wikiData: Q105177237