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(2S,3S,4R,9E)-1,3,4-trihydroxyl-2-[(2'R)-2'-hydroxytetracosanoylamino]-9-octadecene

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID e0268bd7-1e62-4f09-93c4-071d03b172ec
Taxonomy Lipids and lipid-like molecules > Sphingolipids > Ceramides > Phytoceramides
IUPAC Name (2R)-2-hydroxy-N-[(E,2S,3S,4R)-1,3,4-trihydroxyoctadec-9-en-2-yl]tetracosanamide
SMILES (Canonical) CCCCCCCCCCCCCCCCCCCCCCC(C(=O)NC(CO)C(C(CCCCC=CCCCCCCCC)O)O)O
SMILES (Isomeric) CCCCCCCCCCCCCCCCCCCCCC[C@H](C(=O)N[C@@H](CO)[C@@H]([C@@H](CCCC/C=C/CCCCCCCC)O)O)O
InChI InChI=1S/C42H83NO5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-40(46)42(48)43-38(37-44)41(47)39(45)35-33-31-29-27-25-16-14-12-10-8-6-4-2/h25,27,38-41,44-47H,3-24,26,28-37H2,1-2H3,(H,43,48)/b27-25+/t38-,39+,40+,41-/m0/s1
InChI Key NDAGVZHFRAVTBZ-VYECVMTFSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C42H83NO5
Molecular Weight 682.10 g/mol
Exact Mass 681.62712475 g/mol
Topological Polar Surface Area (TPSA) 110.00 Ų
XlogP 14.90
Atomic LogP (AlogP) 10.63
H-Bond Acceptor 5
H-Bond Donor 5
Rotatable Bonds 38

Synonyms

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CHEBI:69540
(2R)-2-hydroxy-N-[(E,2S,3S,4R)-1,3,4-trihydroxyoctadec-9-en-2-yl]tetracosanamide
Q27137880
(2R)-N-[(1S,2S,3R,8E)-1-(Hydroxymethyl)-2,3-dihydroxy-8-heptadecenyl]-2-hydroxytetracosanamide

2D Structure

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2D Structure of (2S,3S,4R,9E)-1,3,4-trihydroxyl-2-[(2'R)-2'-hydroxytetracosanoylamino]-9-octadecene

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8634 86.34%
Caco-2 - 0.8587 85.87%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.8131 81.31%
OATP2B1 inhibitior - 0.5661 56.61%
OATP1B1 inhibitior + 0.8673 86.73%
OATP1B3 inhibitior + 0.9104 91.04%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8879 88.79%
BSEP inhibitior + 0.7009 70.09%
P-glycoprotein inhibitior + 0.5896 58.96%
P-glycoprotein substrate - 0.6606 66.06%
CYP3A4 substrate + 0.5330 53.30%
CYP2C9 substrate - 0.6085 60.85%
CYP2D6 substrate - 0.8448 84.48%
CYP3A4 inhibition - 0.8064 80.64%
CYP2C9 inhibition - 0.6822 68.22%
CYP2C19 inhibition - 0.8802 88.02%
CYP2D6 inhibition + 0.5100 51.00%
CYP1A2 inhibition + 0.5962 59.62%
CYP2C8 inhibition - 0.8781 87.81%
CYP inhibitory promiscuity - 0.8268 82.68%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8800 88.00%
Carcinogenicity (trinary) Non-required 0.7225 72.25%
Eye corrosion - 0.9822 98.22%
Eye irritation - 0.8839 88.39%
Skin irritation - 0.8722 87.22%
Skin corrosion - 0.9834 98.34%
Ames mutagenesis - 0.8600 86.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4130 41.30%
Micronuclear + 0.5100 51.00%
Hepatotoxicity - 0.6963 69.63%
skin sensitisation - 0.9076 90.76%
Respiratory toxicity - 0.7000 70.00%
Reproductive toxicity - 0.7243 72.43%
Mitochondrial toxicity - 0.7375 73.75%
Nephrotoxicity + 0.4599 45.99%
Acute Oral Toxicity (c) III 0.5952 59.52%
Estrogen receptor binding + 0.7456 74.56%
Androgen receptor binding - 0.5265 52.65%
Thyroid receptor binding - 0.5905 59.05%
Glucocorticoid receptor binding + 0.5443 54.43%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.6269 62.69%
Honey bee toxicity - 0.9752 97.52%
Biodegradation - 0.5750 57.50%
Crustacea aquatic toxicity + 0.6586 65.86%
Fish aquatic toxicity - 0.4884 48.84%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL2581 P07339 Cathepsin D 98.51% 98.95%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 98.06% 97.29%
CHEMBL3060 Q9Y345 Glycine transporter 2 97.81% 99.17%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 96.81% 92.86%
CHEMBL4040 P28482 MAP kinase ERK2 95.75% 83.82%
CHEMBL3359 P21462 Formyl peptide receptor 1 93.32% 93.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.94% 96.09%
CHEMBL230 P35354 Cyclooxygenase-2 90.66% 89.63%
CHEMBL4769 O95749 Geranylgeranyl pyrophosphate synthetase 90.00% 92.08%
CHEMBL5043 Q6P179 Endoplasmic reticulum aminopeptidase 2 89.28% 91.81%
CHEMBL1907591 P30926 Neuronal acetylcholine receptor; alpha4/beta4 88.93% 100.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 88.76% 96.47%
CHEMBL4227 P25090 Lipoxin A4 receptor 88.04% 100.00%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 87.23% 89.34%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 86.91% 96.95%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 85.81% 91.24%
CHEMBL4588 P22894 Matrix metalloproteinase 8 84.45% 94.66%
CHEMBL1781 P11387 DNA topoisomerase I 84.27% 97.00%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 83.38% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 83.36% 94.73%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 83.31% 95.71%
CHEMBL2664 P23526 Adenosylhomocysteinase 83.29% 86.67%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.88% 94.33%
CHEMBL2885 P07451 Carbonic anhydrase III 82.40% 87.45%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 81.76% 96.38%
CHEMBL221 P23219 Cyclooxygenase-1 80.95% 90.17%
CHEMBL299 P17252 Protein kinase C alpha 80.84% 98.03%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.39% 98.75%
CHEMBL340 P08684 Cytochrome P450 3A4 80.30% 91.19%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Physalis philadelphica
Rubia yunnanensis

Cross-Links

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PubChem 11765141
NPASS NPC71633
LOTUS LTS0110773
wikiData Q27137880