[(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-(3-methylbut-2-enoyloxy)oxan-3-yl] dodecanoate

Details

• Internal ID: 6aed4b8a-553a-4891-9d8d-e1c052f3576d
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: [(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-(3-methylbut-2-enoyloxy)oxan-3-yl] dodecanoate
• SMILES (Canonical): CCCCCCCCCCCC(=O)OC1C(C(C(OC1OC2(C(C(C(O2)CO)O)O)CO)CO)O)OC(=O)C=C(C)C
• SMILES (Isomeric): CCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O[C@@]2([C@@H]([C@H]([C@@H](O2)CO)O)O)CO)CO)O)OC(=O)C=C(C)C
• InChI: InChI=1S/C29H50O13/c1-4-5-6-7-8-9-10-11-12-13-21(33)39-26-25(40-22(34)14-18(2)3)23(35)19(15-30)38-28(26)42-29(17-32)27(37)24(36)20(16-31)41-29/h14,19-20,23-28,30-32,35-37H,4-13,15-17H2,1-3H3/t19-,20+,23-,24+,25+,26-,27-,28-,29-/m1/s1
• InChI Key: KWJCIFYBGHTTIJ-XXSCEOMOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₅₀O₁₃
• Molecular Weight: 606.70 g/mol
• Exact Mass: 606.32514165 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 0.59
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 18

Synonyms

• CHEMBL447892

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8507	85.07%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.8872	88.72%
OATP2B1 inhibitior	-	0.7194	71.94%
OATP1B1 inhibitior	+	0.8200	82.00%
OATP1B3 inhibitior	+	0.8989	89.89%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8740	87.40%
P-glycoprotein inhibitior	+	0.5933	59.33%
P-glycoprotein substrate	-	0.5954	59.54%
CYP3A4 substrate	+	0.6437	64.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8946	89.46%
CYP3A4 inhibition	-	0.6380	63.80%
CYP2C9 inhibition	-	0.7680	76.80%
CYP2C19 inhibition	-	0.7971	79.71%
CYP2D6 inhibition	-	0.9104	91.04%
CYP1A2 inhibition	-	0.8330	83.30%
CYP2C8 inhibition	+	0.4929	49.29%
CYP inhibitory promiscuity	-	0.8996	89.96%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6440	64.40%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9249	92.49%
Skin irritation	-	0.6782	67.82%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7262	72.62%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8999	89.99%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5701	57.01%
Acute Oral Toxicity (c)	III	0.6153	61.53%
Estrogen receptor binding	+	0.7441	74.41%
Androgen receptor binding	+	0.5633	56.33%
Thyroid receptor binding	-	0.5983	59.83%
Glucocorticoid receptor binding	-	0.5452	54.52%
Aromatase binding	+	0.5668	56.68%
PPAR gamma	+	0.5531	55.31%
Honey bee toxicity	-	0.7425	74.25%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6279	62.79%
Fish aquatic toxicity	+	0.9684	96.84%

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	97.88%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.69%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.13%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.39%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	95.07%	92.50%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.40%	92.86%
CHEMBL299	P17252	Protein kinase C alpha	91.15%	98.03%
CHEMBL3401	O75469	Pregnane X receptor	90.97%	94.73%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	90.70%	82.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.25%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.03%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.31%	91.24%
CHEMBL230	P35354	Cyclooxygenase-2	88.11%	89.63%
CHEMBL2996	Q05655	Protein kinase C delta	87.80%	97.79%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	87.56%	92.08%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.60%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.35%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.14%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.85%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.14%	91.19%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.05%	97.29%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.85%	93.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.84%	96.61%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.51%	94.33%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	80.66%	91.81%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.61%	92.32%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.14%	96.90%

Plants that contains it

• Myristica fragrans
• Physalis viscosa

Cross-Links

• PubChem: 21575480
• LOTUS: LTS0264266
• wikiData: Q105221216