2-({3-[2-(benzenesulfonyl)acetamido]-1,4,5-trihydroxycyclohexyl}formamido)-3-(4-methoxyphenyl)propenamide



Compound IDCDAMM00215
Common name2-({3-[2-(benzenesulfonyl)acetamido]-1,4,5-trihydroxycyclohexyl}formamido)-3-(4-methoxyphenyl)propenamide
IUPAC nameN-[1-amino-3-(4-methoxyphenyl)-1-oxopropan-2-yl]-3-[[2-(benzenesulfonyl)acetyl]amino]-1,4,5-trihydroxycyclohexane-1-carboxamide
Molecular formulaC25H31N3O9S

Experimental data

Retention time19.82
Adduct[M+H]+
Actual mz550.185
Theoretical mz550.185
Error0.67
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score4.6108

Identifiers and class information

Inchi keyNMNKOBRDMPMYPS-UHFFFAOYSA-N
SmilesCOC1=CC=C(C=C1)CC(C(=O)N)NC(=O)C2(CC(C(C(C2)O)O)NC(=O)CS(=O)(=O)C3=CC=CC=C3)O
SuperclassOrganic acids and derivatives
ClassPeptidomimetics

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)3
Number of rotatable bonds (#rotor)13
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)549.595
Computed dipole moment(dipole)6.345
Total solvent accessible surface area (SASA)739.252
Hydrophobic component of SASA (FOSA)208.053
Hydrophilic component of SASA (FISA)298.442
Pie component of the SASA (PISA)232.757
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1490.17
Number of hydrogen bond donors (donorHB)5.25
Number of hydrogen bond acceptors (accptHB)14.65
Free energy of solvation of dipole (dip^2/V)0.027014
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0454072
Globularity descriptor (glob)0.853487
Predicted polarizability in cubic angstroms (QPpolrz)47.358
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.838
Predicted octanol/gas partition coefficient (QPlogPoct)32.45
Predicted water/gas partition coefficient (QPlogPw)30.115
Predicted octanol/water partition coefficient (QPlogPo/w)-1.348
Predicted aqueous solubility (QPlogS)-0.297
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.134
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-0.89
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)3.524
Predicted brain/blood partition coefficient (QPlogBB)-2.951
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)5.15
Predicted skin permeability, log Kp (QPlogKp)-4.952
PM3 calculated ionization potential (IP(ev))8.906
PM3 calculated electron affinity (EA(eV))0.775
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-1.492
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)77.731
Van der Waals surface area (PSA)220.851
Number of nitrogen and oxygen atoms (#NandO)12
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
P00734F2ThrombinT94033SEA
Q9NTG7SIRT3NAD-dependent deacetylase sirtuin 3T91959SEA
P08514ITGA2BIntegrin alpha-IIb/beta-3T50688SEA
P00747PLGPlasminogenT89034SEA
Q6B0I6KDM4DLysine-specific demethylase 4DT17036SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
P17706PTPN2T-cell protein-tyrosine phosphataseT49156SEA
P08253MMP2Matrix metalloproteinase 2T68251SEA
P22894MMP8Matrix metalloproteinase 8T08856SEA
P08254MMP3Matrix metalloproteinase 3T86702SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03956MMP1Matrix metalloproteinase 1T52450SEA
P17655CAPN2Calpain 2T86837SEA
P62993GRB2Growth factor receptor-bound protein 2T30926SEA
P45452MMP13Matrix metalloproteinase 13T34296SEA
P78536ADAM17ADAM17T82393SEA
P09237MMP7Matrix metalloproteinase 7T73475SEA
P13497BMP1Bone morphogenetic protein 1T53350SEA
P04229HLA-DRB1HLA class II histocompatibility antigen DRB1-1T83611SEA
P07858CTSBCathepsin (B and K)T61746SEA
Q01726MC1RMelanocortin receptor 1T35842SEA
P00750PLATTissue-type plasminogen activatorT45299SEA
Q9BYF1ACE2Angiotensin-converting enzyme 2T27889SEA
P42892ECE1Endothelin-converting enzyme 1T50970SEA
P05556ITGB1Integrin alpha2/beta1T01851SEA
P39900MMP12Matrix metalloproteinase 12T03500SEA
P15085CPA1Carboxypeptidase A1T33966SEA
P00749PLAUUrokinase-type plasminogen activatorT17758SEA
P03952KLKB1Plasma kallikreinT82739SEA
P26010ITGB7Integrin alpha-4/beta-7T07403SEA
P42226STAT6Signal transducer and activator of transcription 6T20585SEA
P28065PSMB9Proteasome subunit beta type-9T06792SEA
P28062PSMB8Proteasome subunit beta type-8T77350SEA
Q8IU80TMPRSS6Transmembrane protease serine 6T13863SEA
Q9Y5Y6ST14MatriptaseT31543SEA
P51512MMP16Matrix metalloproteinase 16T35824SEA
P51511MMP15Matrix metalloproteinase 15T81658SEA
Q13451FKBP5Peptidyl-prolyl cis-trans isomerase FKBP5T98337SEA
P06734FCER2Immunoglobulin epsilon Fc receptorT67207SEA
P13612ITGA4Integrin alpha-4T97587SEA
Q00975CACNA1BVoltage-gated N-type calcium channel alpha-1B subunitT38338SEA
Q9Y337KLK5Kallikrein 5T11808SEA
P40306PSMB1026S proteosomeT09022SEA
P51787KCNQ1Voltage-gated potassium channel subunit Kv7.1T49526SEA
Q9GZQ6NPFFR1Neuropeptide FF receptor 1T79780SEA
Q9Y5X5NPFFR2Neuropeptide FF receptor 2T90818SEA
Q9BY41HDAC8Histone deacetylase 8T28887SEA
P05106ITGB3Integrin beta-3T26457SEA
P25786PSMA1Core proteasome 20S complexT61997SEA
P28072PSMB6Proteasome beta-1T54973SEA
Q99436PSMB7Proteasome beta-2T55986SEA
P23467PTPRBProtein tyrosine phosphatase betaT57034SEA
P14672GLUT4Glucose transporter type 4T67658SEA
P26012ITGB8Integrin beta-8T64597SEA
P01589IL2RAInterleukin 2 receptor alphaT03313SEA
P01008SERPINC1Antithrombin-IIIT73476SEA
Q9HCN6GP6Platelet glycoprotein VIT60514SEA
P41587VIPR2Helodermin-preferring VIP receptorT06182SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T94033DI0052Bleeding disorder[ICD-11: GA20-GA21]P00734F2
T94033DI0091Coagulation defect[ICD-11: 3B10]P00734F2
T94033DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P00734F2
T94033DI0275Multiple sclerosis[ICD-11: 8A40]P00734F2
T94033DI0287Myocardial infarction[ICD-11: BA41-BA43]P00734F2
T94033DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00734F2
T94033DI0403Thrombocytopenia[ICD-11: 3B64]P00734F2
T94033DI0405Thrombosis[ICD-11: DB61-GB90]P00734F2
T50688DI0007Acquired hypermelanosis[ICD-11: ED60]P08514ITGA2B
T50688DI0030Angina pectoris[ICD-11: BA40]P08514ITGA2B
T50688DI0287Myocardial infarction[ICD-11: BA41-BA43]P08514ITGA2B
T89034DI0030Angina pectoris[ICD-11: BA40]P00747PLG
T89034DI0052Bleeding disorder[ICD-11: GA20-GA21]P00747PLG
T89034DI0254Menopausal disorder[ICD-11: GA30]P00747PLG
T89034DI0287Myocardial infarction[ICD-11: BA41-BA43]P00747PLG
T89034DI0345Procedure injury[ICD-11: NE81]P00747PLG
T89034DI0357Pulmonary thromboembolism[ICD-11: BB00]P00747PLG
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
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T86837DI0106COVID-19[ICD-11: 1D6Y]P17655CAPN2
T30926DI0012Acute myeloid leukaemia[ICD-11: 2A60]P62993GRB2
T30926DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P62993GRB2
T30926DI0250Mature B-cell lymphoma[ICD-11: 2A85]P62993GRB2
T30926DI0284Myelodysplastic syndrome[ICD-11: 2A37]P62993GRB2
T30926DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P62993GRB2
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T83611DI0275Multiple sclerosis[ICD-11: 8A40]P04229HLA-DRB1
T61746DI0023Alopecia[ICD-11: ED70]P07858CTSB
T61746DI0025Alzheimer disease[ICD-11: 8A20]P07858CTSB
T61746DI0037Asthma[ICD-11: CA23]P07858CTSB
T61746DI0055Bone cancer[ICD-11: 2B5Z]P07858CTSB
T61746DI0060Brain cancer[ICD-11: 2A00]P07858CTSB
T61746DI0067Cardiac arrest[ICD-11: MC82]P07858CTSB
T61746DI0074Cerebral ischaemic stroke[ICD-11: 8B11]P07858CTSB
T61746DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P07858CTSB
T61746DI0087Chronic pain[ICD-11: MG30]P07858CTSB
T61746DI0110Cystic fibrosis[ICD-11: CA25]P07858CTSB
T61746DI0124Digestive system disease[ICD-11: DE2Z]P07858CTSB
T61746DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P07858CTSB
T61746DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P07858CTSB
T61746DI0253Meningioma[ICD-11: 2A01]P07858CTSB
T61746DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P07858CTSB
T61746DI0275Multiple sclerosis[ICD-11: 8A40]P07858CTSB
T61746DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]P07858CTSB
T61746DI0320Osteoarthritis[ICD-11: FA00-FA05]P07858CTSB
T61746DI0351Psoriasis[ICD-11: EA90]P07858CTSB
T61746DI0366Rheumatoid arthritis[ICD-11: FA20]P07858CTSB
T35842DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]Q01726MC1R
T35842DI0205Inborn porphyrin/heme metabolism error[ICD-11: 5C58]Q01726MC1R
T45299DI0052Bleeding disorder[ICD-11: GA20-GA21]P00750PLAT
T45299DI0345Procedure injury[ICD-11: NE81]P00750PLAT
T27889DI0009Acute diabete complication[ICD-11: 5A2Y]Q9BYF1ACE2
T27889DI0217Intrathoracic organs injury[ICD-11: NB32]Q9BYF1ACE2
T27889DI0356Pulmonary hypertension[ICD-11: BB01]Q9BYF1ACE2
T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T17758DI0211Inherited coagulation factor deficiency[ICD-11: 3B14]P00749PLAU
T17758DI0287Myocardial infarction[ICD-11: BA41-BA43]P00749PLAU
T82739DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P03952KLKB1
T82739DI0364Retinal vascular occlusion[ICD-11: 9B74]P03952KLKB1
T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
T77350DI0274Multiple myeloma[ICD-11: 2A83]P28062PSMB8
T67207DI0231Leukaemia[ICD-11: 2A60-2B33]P06734FCER2
T97587DI0107Crohn disease[ICD-11: DD70]P13612ITGA4
T97587DI0275Multiple sclerosis[ICD-11: 8A40]P13612ITGA4
T97587DI0419Ulcerative colitis[ICD-11: DD71]P13612ITGA4
T38338DI0264Migraine[ICD-11: 8A80]Q00975CACNA1B
T38338DI0305Non-thrombocytopenic purpura[ICD-11: 3B60]Q00975CACNA1B
T38338DI0324Pain[ICD-11: MG30-MG3Z]Q00975CACNA1B
T49526DI0190Hypertension[ICD-11: BA00-BA04]P51787KCNQ1
T28887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9BY41HDAC8
T57034DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P23467PTPRB
T57034DI0365Retinopathy[ICD-11: 9B71]P23467PTPRB
T67658DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P14672GLUT4
T64597DI0083Chronic kidney disease[ICD-11: GB61]P26012ITGB8
T03313DI0413Transplant rejection[ICD-11: NE84]P01589IL2RA
T73476DI0091Coagulation defect[ICD-11: 3B10]P01008SERPINC1
T73476DI0103Coronary thrombosis[ICD-11: BA43]P01008SERPINC1
T73476DI0114Deep vein thrombosis[ICD-11: BD71]P01008SERPINC1
T73476DI0410Tinnitus[ICD-11: MC41]P01008SERPINC1
T60514DI0035Arterial occlusive disease[ICD-11: BD40]Q9HCN6GP6
T60514DI0074Cerebral ischaemic stroke[ICD-11: 8B11]Q9HCN6GP6
T06182DI0069Cardiomyopathy[ICD-11: BC43]P41587VIPR2
T06182DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P41587VIPR2
T06182DI0175Heart failure[ICD-11: BD10-BD1Z]P41587VIPR2
T06182DI0190Hypertension[ICD-11: BA00-BA04]P41587VIPR2
T06182DI0280Muscular dystrophy[ICD-11: 8C70]P41587VIPR2
T06182DI0356Pulmonary hypertension[ICD-11: BB01]P41587VIPR2

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