Butyl 4\'-O-hexadecanoyl-neohesperidoside



Compound IDCDAMM01695
Common nameButyl 4\'-O-hexadecanoyl-neohesperidoside
IUPAC name[6-[2-butoxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] hexadecanoate
Molecular formulaC32H60O11

Experimental data

Retention time7.6
Adduct[M+H]+
Actual mz621.417
Theoretical mz621.421
Error6.4
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.2629

Identifiers and class information

Inchi keyGSHHCUYNHSPHDT-JZFUURNRNA-N
SmilesO=C(OC1C(O)C(O)C(OC1C)OC2C(OCCCC)OC(CO)C(O)C2O)CCCCCCCCCCCCCCC
SuperclassLipids and lipid-like molecules
ClassFatty Acyls

Pharmacokinetic properties

Number of descriptor values(#stars)8
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)0
Number of rotatable bonds (#rotor)27
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)620.819
Computed dipole moment(dipole)3.83
Total solvent accessible surface area (SASA)1165.58
Hydrophobic component of SASA (FOSA)963.68
Hydrophilic component of SASA (FISA)201.897
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)2146.42
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)17.3
Free energy of solvation of dipole (dip^2/V)0.0068329
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0331887
Globularity descriptor (glob)0.690399
Predicted polarizability in cubic angstroms (QPpolrz)62.409
Predicted hexadecane/gas partition coefficient (QPlogPC16)22.016
Predicted octanol/gas partition coefficient (QPlogPoct)36.484
Predicted water/gas partition coefficient (QPlogPw)22.305
Predicted octanol/water partition coefficient (QPlogPo/w)3.449
Predicted aqueous solubility (QPlogS)-6.161
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.803
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.542
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)120.589
Predicted brain/blood partition coefficient (QPlogBB)-3.888
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)50.275
Predicted skin permeability, log Kp (QPlogKp)-2.648
PM3 calculated ionization potential (IP(ev))10.485
PM3 calculated electron affinity (EA(eV))-0.734
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.41
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)58.473
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
Van der Waals surface area (PSA)166.406
Number of nitrogen and oxygen atoms (#NandO)11
Number of violations of Lipinski’s rule of five (RuleOfFive)2
Number of violations of Jorgensen’s rule of three (RuleOfThree)1

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
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
O00206TLR4Toll-like receptor 4 (by homology)T81443SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
Q9Y251HPSEHeparanaseT47623SEA
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P60568IL2Interleukin-2T61698SEA
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
O00142TK2Thymidine kinase, mitochondrialT22976SEA
P16885PLCG2Phospholipase C-gamma-2T93922SEA
P11717IGF2RInsulin-like growth factor II receptorT59550SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
Q9UMJ8GBA1Lysosomal acid glucosylceramidaseT63243SEA
Q07108CD69Early activation antigen CD69T48780SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T81443DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]O00206TLR4
T81443DI0346Prostate cancer[ICD-11: 2C82]O00206TLR4
T81443DI0375Sepsis[ICD-11: 1G40-1G41]O00206TLR4
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
T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
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
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
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
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T22976DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]O00142TK2
T59550DI0146Fibrosis[ICD-11: GA14-GC01]P11717IGF2R
T59550DI0368Sarcoidosis[ICD-11: 4B20]P11717IGF2R
T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
T63243DI0242Lysosomal disease[ICD-11: 5C56]Q9UMJ8GBA1

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