N-[(4E,8Z)-1,3-dihydroxyoctadeca-4,8-dien-2-yl]hexadecanamide 1-glucoside



Compound IDCDAMM00892
Common nameN-[(4E,8Z)-1,3-dihydroxyoctadeca-4,8-dien-2-yl]hexadecanamide 1-glucoside
IUPAC nameN-[3-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]hexadecanamide
Molecular formulaC40H75NO8

Experimental data

Retention time15.99
Adduct[M+H]+
Actual mz698.557
Theoretical mz698.556
Error1.32
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2774

Identifiers and class information

Inchi keyVCLOTRNDBUPTQD-ZNPGVSGMNA-N
SmilesO=C(NC(COC1OC(CO)C(O)C(O)C1O)C(O)C=CCCC=CCCCCCCCCC)CCCCCCCCCCCCCCC
SuperclassLipids and lipid-like molecules
ClassSphingolipids

Pharmacokinetic properties

Number of descriptor values(#stars)13
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)0
Number of non-conjugated amide groups (#amide)1
Number of rotatable bonds (#rotor)37
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)698.034
Computed dipole moment(dipole)8.031
Total solvent accessible surface area (SASA)1422.91
Hydrophobic component of SASA (FOSA)1196.5
Hydrophilic component of SASA (FISA)205.462
Pie component of the SASA (PISA)20.947
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)2617.66
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)14.4
Free energy of solvation of dipole (dip^2/V)0.0246418
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0247891
Globularity descriptor (glob)0.645552
Predicted polarizability in cubic angstroms (QPpolrz)75.047
Predicted hexadecane/gas partition coefficient (QPlogPC16)28.053
Predicted octanol/gas partition coefficient (QPlogPoct)40.498
Predicted water/gas partition coefficient (QPlogPw)21.593
Predicted octanol/water partition coefficient (QPlogPo/w)6.637
Predicted aqueous solubility (QPlogS)-8.747
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.616
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.993
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)66.32
Predicted brain/blood partition coefficient (QPlogBB)-4.953
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)46.219
Predicted skin permeability, log Kp (QPlogKp)-1.68
PM3 calculated ionization potential (IP(ev))9.444
PM3 calculated electron affinity (EA(eV))-1.017
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)0.439
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)59.536
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)28.375
Van der Waals surface area (PSA)154.974
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)3
Number of violations of Jorgensen’s rule of three (RuleOfThree)2

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SEA
P21554CNR1Cannabinoid receptor 1 (by homology)T76685SEA
P34913EPHX2Epoxide hydrataseT35734SEA
O00519FAAHAnandamide amidohydrolaseT11754SEA
P16581SELESelectin ET72835SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
Q8TDS5OXER1Oxoeicosanoid receptor 1T68834SEA
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P17931LGALS3Galectin-3T72038SEA
Q9NRA0SPHK2Sphingosine kinase 2T31989SEA
Q9HBW0LPAR2Lysophosphatidic acid receptor Edg-4T39380SEA
P43657LPAR6Lysophosphatidic acid receptor 6T13484SEA
O00142TK2Thymidine kinase, mitochondrialT22976SEA
Q9UPC5GPR34Probable G-protein coupled receptor 34T73859SEA
O00398P2RY10Putative P2Y purinoceptor 10T00488SEA
Q9BXC1GPR174Probable G-protein coupled receptor 174T87661SEA
Q9UBY5LPAR3Lysophosphatidic acid receptor Edg-7T95923SEA
Q92633LPAR1Lysophosphatidic acid receptor Edg-2T92640SEA
Q99677LPAR4Lysophosphatidic acid receptor 4T58130SEA
O60603TLR2Toll-like receptor 2T82078SEA
O15269SPTLC1Serine palmitoyltransferaseT30817SEA
Q92959SLCO2A1Prostaglandin transporterT15518SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T76685DI0031Anorexia nervosa[ICD-11: 6B80]P21554CNR1
T76685DI0214Insomnia[ICD-11: 7A00-7A0Z]P21554CNR1
T76685DI0308Obesity[ICD-11: 5B80-5B81]P21554CNR1
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
T11754DI0101Corneal disease[ICD-11: 9A76-9A78]O00519FAAH
T72835DI0012Acute myeloid leukaemia[ICD-11: 2A60]P16581SELE
T72835DI0037Asthma[ICD-11: CA23]P16581SELE
T72835DI0039Atopic eczema[ICD-11: EA80]P16581SELE
T72835DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P16581SELE
T72835DI0088Circulatory system disease[ICD-11: BE2Z]P16581SELE
T72835DI0190Hypertension[ICD-11: BA00-BA04]P16581SELE
T72835DI0351Psoriasis[ICD-11: EA90]P16581SELE
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
T60526DI0037Asthma[ICD-11: CA23]P14151SELL
T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
T31989DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9NRA0SPHK2
T22976DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]O00142TK2
T95923DI0146Fibrosis[ICD-11: GA14-GC01]Q9UBY5LPAR3
T95923DI0399Systemic sclerosis[ICD-11: 4A42]Q9UBY5LPAR3
T92640DI0146Fibrosis[ICD-11: GA14-GC01]Q92633LPAR1
T92640DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q92633LPAR1
T92640DI0351Psoriasis[ICD-11: EA90]Q92633LPAR1
T92640DI0399Systemic sclerosis[ICD-11: 4A42]Q92633LPAR1
T82078DI0346Prostate cancer[ICD-11: 2C82]O60603TLR2
T30817DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]O15269SPTLC1

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