3-(2,3-dihydro-1-benzofuran-5-yl)-N-[1-hydroxy-4-(methylsulfanyl)butan-2-yl]propenamide



Compound IDCDAMM00123
Common name3-(2,3-dihydro-1-benzofuran-5-yl)-N-[1-hydroxy-4-(methylsulfanyl)butan-2-yl]propenamide
IUPAC name3-(2,3-dihydro-1-benzofuran-5-yl)-N-(1-hydroxy-4-methylsulfanylbutan-2-yl)propanamide
Molecular formulaC16H23NO3S

Experimental data

Retention time59.96
Adduct[M+H]+
Actual mz310.147
Theoretical mz310.147
Error1.09
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score4.8389

Identifiers and class information

Inchi keyORLUDQBZHLUNIF-UHFFFAOYSA-N
SmilesCSCCC(CO)NC(=O)CCC1=CC2=C(C=C1)OCC2
SuperclassOrganoheterocyclic compounds
ClassCoumarans

Pharmacokinetic properties

Number of descriptor values(#stars)0
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)9
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)309.423
Computed dipole moment(dipole)6.05
Total solvent accessible surface area (SASA)598.141
Hydrophobic component of SASA (FOSA)373.562
Hydrophilic component of SASA (FISA)74.046
Pie component of the SASA (PISA)116.147
Weakly polar component of the SASA (WPSA)34.386
Total solvent accesible volume (volume)1045.42
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)5.45
Free energy of solvation of dipole (dip^2/V)0.0350109
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0128857
Globularity descriptor (glob)0.832825
Predicted polarizability in cubic angstroms (QPpolrz)31.014
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.939
Predicted octanol/gas partition coefficient (QPlogPoct)15.888
Predicted water/gas partition coefficient (QPlogPw)10.001
Predicted octanol/water partition coefficient (QPlogPo/w)2.562
Predicted aqueous solubility (QPlogS)-3.32
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.084
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.417
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1452.19
Predicted brain/blood partition coefficient (QPlogBB)-0.606
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1585.6
Predicted skin permeability, log Kp (QPlogKp)-1.611
PM3 calculated ionization potential (IP(ev))8.561
PM3 calculated electron affinity (EA(eV))-0.168
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)-0.32
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)16.545
Van der Waals surface area (PSA)65.572
Number of nitrogen and oxygen atoms (#NandO)4
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q16739UGCGCeramide glucosyltransferaseT14908SEA
P22894MMP8Matrix metalloproteinase 8T08856SEA
P45452MMP13Matrix metalloproteinase 13T34296SEA
P23946CMA1ChymaseT05114SEA
P48039MTNR1AMelatonin receptor 1AT97613SEA
P49286MTNR1BMelatonin receptor 1BT48268SEA
P39900MMP12Matrix metalloproteinase 12T03500SEA
P09238MMP10Matrix metalloproteinase 10T40488SEA
Q9UKP6UTS2RUrotensin II receptorT49072SEA
Q08752PPIDPeptidyl-prolyl cis-trans isomerase DT52447SEA
P49682CXCR3C-X-C chemokine receptor type 3T25315SEA
P04632CAPNS1HUMAN calpain-1 or calpain small subunit 1 heterodimerT00099SEA
Q7RTX1TAS1R1Taste receptorT41263SEA
P02778CXCL10C-X-C motif chemokine 10T30635SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T14908DI0242Lysosomal disease[ICD-11: 5C56]Q16739UGCG
T14908DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]Q16739UGCG
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T05114DI0039Atopic eczema[ICD-11: EA80]P23946CMA1
T05114DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P23946CMA1
T05114DI0169Gram-positive bacterial infection[ICD-11: 1B74-1F40]P23946CMA1
T05114DI0175Heart failure[ICD-11: BD10-BD1Z]P23946CMA1
T05114DI0229Left ventricular failure[ICD-11: BD11]P23946CMA1
T05114DI0287Myocardial infarction[ICD-11: BA41-BA43]P23946CMA1
T97613DI0214Insomnia[ICD-11: 7A00-7A0Z]P48039MTNR1A
T48268DI0214Insomnia[ICD-11: 7A00-7A0Z]P49286MTNR1B
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T49072DI0037Asthma[ICD-11: CA23]Q9UKP6UTS2R
T25315DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P49682CXCR3
T25315DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P49682CXCR3
T25315DI0351Psoriasis[ICD-11: EA90]P49682CXCR3
T25315DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P49682CXCR3
T00099DI0106COVID-19[ICD-11: 1D6Y]P04632CAPNS1
T41263DI0078Cholera[ICD-11: 1A00]Q7RTX1TAS1R1
T30635DI0107Crohn disease[ICD-11: DD70]P02778CXCL10
T30635DI0120Diabetes mellitus[ICD-11: 5A10]P02778CXCL10
T30635DI0200Immune system disease[ICD-11: 4A01-4B41]P02778CXCL10
T30635DI0207Indeterminate colitis[ICD-11: DD72]P02778CXCL10
T30635DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P02778CXCL10
T30635DI0419Ulcerative colitis[ICD-11: DD71]P02778CXCL10

Copyright © 2025