Lup-20(29)en-28-al-3beta-yl caffeate



Compound IDCDAMM01804
Common nameLup-20(29)en-28-al-3beta-yl caffeate
IUPAC name(3a-formyl-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl) 3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular formulaC39H54O5

Experimental data

Retention time10.04
Adduct[M+H]+
Actual mz603.41
Theoretical mz603.404
Error9.98
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5097

Identifiers and class information

Inchi keyGRALPKTVLYGKSY-HJXQZQOMNA-N
SmilesO=CC12CCC(C(=C)C)C2C3CCC4C5(C)CCC(OC(=O)C=CC6=CC=C(O)C(O)=C6)C(C)(C)C5CCC4(C)C3(C)CC1
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)4
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)8
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)602.853
Computed dipole moment(dipole)3.277
Total solvent accessible surface area (SASA)917.468
Hydrophobic component of SASA (FOSA)561.194
Hydrophilic component of SASA (FISA)196.007
Pie component of the SASA (PISA)160.267
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1844.83
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)5.5
Free energy of solvation of dipole (dip^2/V)0.0058205
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0084779
Globularity descriptor (glob)0.792889
Predicted polarizability in cubic angstroms (QPpolrz)64.07
Predicted hexadecane/gas partition coefficient (QPlogPC16)18.177
Predicted octanol/gas partition coefficient (QPlogPoct)27.768
Predicted water/gas partition coefficient (QPlogPw)10.933
Predicted octanol/water partition coefficient (QPlogPo/w)7.26
Predicted aqueous solubility (QPlogS)-9.465
Conformation-independent predicted aqueous solubility (CIQPlogS)-9.487
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.648
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)137.142
Predicted brain/blood partition coefficient (QPlogBB)-1.997
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)57.774
Predicted skin permeability, log Kp (QPlogKp)-3.799
PM3 calculated ionization potential (IP(ev))8.919
PM3 calculated electron affinity (EA(eV))0.822
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)2.161
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)81.787
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)108.233
Number of nitrogen and oxygen atoms (#NandO)5
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
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
P17706PTPN2T-cell protein-tyrosine phosphataseT49156SEA
Q8TDU6GPBAR1G-protein coupled bile acid receptor 1T86273SEA
P16885PLCG2Phospholipase C-gamma-2T93922SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T49156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P17706PTPN2
T86273DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q8TDU6GPBAR1

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