2-({3-[(cyclohexylcarbamoyl)amino]-1-[2-(methylsulfanyl)acetyl]pyrrolidin-2-yl}formamido)-3-(1H-indol-3-yl)propenamide



Compound IDCDAMM00212
Common name2-({3-[(cyclohexylcarbamoyl)amino]-1-[2-(methylsulfanyl)acetyl]pyrrolidin-2-yl}formamido)-3-(1H-indol-3-yl)propenamide
IUPAC nameN-[1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-3-(cyclohexylcarbamoylamino)-1-(2-methylsulfanylacetyl)pyrrolidine-2-carboxamide
Molecular formulaC26H36N6O4S

Experimental data

Retention time38.83
Adduct[M+H]+
Actual mz529.259
Theoretical mz529.259
Error0.18
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.8152

Identifiers and class information

Inchi keyDBYROVUIAFYQCY-UHFFFAOYSA-N
SmilesCSCC(=O)N1CCC(C1C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)N)NC(=O)NC4CCCCC4
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)2
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)4
Number of rotatable bonds (#rotor)9
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)528.668
Computed dipole moment(dipole)6.149
Total solvent accessible surface area (SASA)922.049
Hydrophobic component of SASA (FOSA)480.78
Hydrophilic component of SASA (FISA)190.981
Pie component of the SASA (PISA)204.258
Weakly polar component of the SASA (WPSA)46.03
Total solvent accesible volume (volume)1667.28
Number of hydrogen bond donors (donorHB)4.25
Number of hydrogen bond acceptors (accptHB)8.75
Free energy of solvation of dipole (dip^2/V)0.0226794
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0195636
Globularity descriptor (glob)0.737481
Predicted polarizability in cubic angstroms (QPpolrz)56.742
Predicted hexadecane/gas partition coefficient (QPlogPC16)18.292
Predicted octanol/gas partition coefficient (QPlogPoct)30.295
Predicted water/gas partition coefficient (QPlogPw)23.256
Predicted octanol/water partition coefficient (QPlogPo/w)2.095
Predicted aqueous solubility (QPlogS)-5.519
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.19
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.256
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)36.793
Predicted brain/blood partition coefficient (QPlogBB)-2.207
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)116.25
Predicted skin permeability, log Kp (QPlogKp)-3.456
PM3 calculated ionization potential (IP(ev))8.369
PM3 calculated electron affinity (EA(eV))0.034
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-0.488
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)41.32
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)77.772
Van der Waals surface area (PSA)169.594
Number of nitrogen and oxygen atoms (#NandO)10
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
P00797RENReninT61622SEA
O15379HDAC3Histone deacetylase 3T05090SEA
P08473MMENeprilysinT05409SEA
P34913EPHX2Epoxide hydrataseT35734SEA
Q92769HDAC2Histone deacetylase 2T51191SEA
P12955PEPDXaa-Pro dipeptidaseT94823SEA
P08253MMP2Matrix metalloproteinase 2T68251SEA
P22894MMP8Matrix metalloproteinase 8T08856SEA
P08254MMP3Matrix metalloproteinase 3T86702SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03956MMP1Matrix metalloproteinase 1T52450SEA
P35372OPRM1Mu opioid receptorT47768SEA
P09237MMP7Matrix metalloproteinase 7T73475SEA
P13497BMP1Bone morphogenetic protein 1T53350SEA
P35270SPRSubstance-P receptorT47094SEA
P07711CTSLCathepsin LT98691SEA
P32245MC4RMelanocortin receptor 4T72458SEA
P07858CTSBCathepsin (B and K)T61746SEA
Q92847GHSRGhrelin receptorT59604SEA
P41143OPRD1Delta opioid receptorT58992SEA
Q01726MC1RMelanocortin receptor 1T35842SEA
P41968MC3RMelanocortin receptor 3T76846SEA
P13500CCL2C-C motif chemokine 2T89988SEA
Q6P179ERAP2Endoplasmic reticulum aminopeptidase 2T65818SEA
P04439HLA-AHLA class I histocompatibility antigen A-3T08985SEA
P25090FPR2Lipoxin A4 receptor (by homology)T97917SEA
P42892ECE1Endothelin-converting enzyme 1T50970SEA
P25101EDNRAEndothelin receptor ET-AT23499SEA
P21730C5AR1C5a anaphylatoxin chemotactic receptorT15439SEA
P35346SSTR5Somatostatin receptor 5T64830SEA
P30874SSTR2Somatostatin receptor 2T53024SEA
P31391SSTR4Somatostatin receptor 4T62974SEA
P30872SSTR1Somatostatin receptor 1T16633SEA
P32745SSTR3Somatostatin receptor 3T13644SEA
P32239CCKBRCholecystokinin B receptor (by homology)T05849SEA
P50281MMP14Matrix metalloproteinase 14T65019SEA
P32238CCKARCholecystokinin A receptorT28330SEA
P24530EDNRBEndothelin receptor ET-BT92828SEA
P14679TYRTyrosinaseT97035SEA
P21452TACR2Neurokinin 2 receptorT52790SEA
P42226STAT6Signal transducer and activator of transcription 6T20585SEA
P29371TACR3Neurokinin 3 receptorT29683SEA
Q9UIQ6LNPEPCystinyl aminopeptidaseT97537SEA
P28065PSMB9Proteasome subunit beta type-9T06792SEA
P28062PSMB8Proteasome subunit beta type-8T77350SEA
Q8IU80TMPRSS6Transmembrane protease serine 6T13863SEA
Q9Y5Y6ST14MatriptaseT31543SEA
P51511MMP15Matrix metalloproteinase 15T81658SEA
P28336NMBRNeuromedin B receptorT68887SEA
P33032MC5RMelanocortin receptor 5T95302SEA
P28336NMBRNeuromedin B receptorT68887SEA
Q13451FKBP5Peptidyl-prolyl cis-trans isomerase FKBP5T98337SEA
P30550GRPRGastrin releasing peptide receptorT99816SEA
Q9H2K8TAOK3Serine/threonine-protein kinase TAO3T63682SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P21462FPR1Formyl peptide receptor 1T87831SEA
Q9Y337KLK5Kallikrein 5T11808SEA
P23284PPIBCyclophilin BT25847SEA
Q04756HGFACHepatocyte growth factor activatorT38584SEA
O43895XPNPEP2Xaa-Pro aminopeptidase 2T68320SEA
P49862KLK7Kallikrein-7T79155SEA
Q06609RAD51DNA repair protein RAD51 homolog 1T63083SEA
O95622ADCY5Adenylate cyclase type 5T19531SEA
P24347MMP11Matrix metalloproteinase-11T73180SEA
P05981HPNSerine protease hepsinT73471SEA
Q9ULZ9MMP17Matrix metalloproteinase-17T55616SEA
Q15678PTPN14Protein-tyrosine phosphatase pezT82848SEA
Q9Y6W6DUSP10Dual specificity protein phosphatase 10T17339SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T61622DI0190Hypertension[ICD-11: BA00-BA04]P00797REN
T05090DI0241Lymphoma[ICD-11: 2A80-2A86]O15379HDAC3
T05090DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O15379HDAC3
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
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
T47768DI0013Acute pain[ICD-11: MG31]P35372OPRM1
T47768DI0059Bowel habit change[ICD-11: ME05]P35372OPRM1
T47768DI0087Chronic pain[ICD-11: MG30]P35372OPRM1
T47768DI0101Corneal disease[ICD-11: 9A76-9A78]P35372OPRM1
T47768DI0105Cough[ICD-11: MD12]P35372OPRM1
T47768DI0117Depression[ICD-11: 6A70-6A7Z]P35372OPRM1
T47768DI0124Digestive system disease[ICD-11: DE2Z]P35372OPRM1
T47768DI0218Irritable bowel syndrome[ICD-11: DD91]P35372OPRM1
T47768DI0228Large intestine motility disorder[ICD-11: DB32]P35372OPRM1
T47768DI0317Opioid use disorder[ICD-11: 6C43]P35372OPRM1
T47768DI0324Pain[ICD-11: MG30-MG3Z]P35372OPRM1
T47768DI0349Pruritus[ICD-11: EC90]P35372OPRM1
T47768DI0374Sensation disturbance[ICD-11: MB40]P35372OPRM1
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
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
T59604DI0087Chronic pain[ICD-11: MG30]Q92847GHSR
T59604DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]Q92847GHSR
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T35842DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]Q01726MC1R
T35842DI0205Inborn porphyrin/heme metabolism error[ICD-11: 5C58]Q01726MC1R
T76846DI0308Obesity[ICD-11: 5B80-5B81]P41968MC3R
T76846DI0378Sexual dysfunction[ICD-11: HA00-HA01]P41968MC3R
T76846DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P41968MC3R
T89988DI0083Chronic kidney disease[ICD-11: GB61]P13500CCL2
T89988DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P13500CCL2
T89988DI0087Chronic pain[ICD-11: MG30]P13500CCL2
T89988DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P13500CCL2
T89988DI0252Melanoma[ICD-11: 2C30]P13500CCL2
T89988DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P13500CCL2
T89988DI0275Multiple sclerosis[ICD-11: 8A40]P13500CCL2
T89988DI0326Pancreatic cancer[ICD-11: 2C10]P13500CCL2
T89988DI0366Rheumatoid arthritis[ICD-11: FA20]P13500CCL2
T89988DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P13500CCL2
T97917DI0025Alzheimer disease[ICD-11: 8A20]P25090FPR2
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T15439DI0431Vasculitis[ICD-11: 4A44]P21730C5AR1
T64830DI0108Cushing syndrome[ICD-11: 5A70]P35346SSTR5
T53024DI0108Cushing syndrome[ICD-11: 5A70]P30874SSTR2
T53024DI0122Diagnostic imaging[ICD-11: N.A.]P30874SSTR2
T53024DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30874SSTR2
T62974DI0087Chronic pain[ICD-11: MG30]P31391SSTR4
T62974DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P31391SSTR4
T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
T13644DI0108Cushing syndrome[ICD-11: 5A70]P32745SSTR3
T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
T28330DI0210Influenza[ICD-11: 1E30-1E32]P32238CCKAR
T28330DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P32238CCKAR
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T52790DI0218Irritable bowel syndrome[ICD-11: DD91]P21452TACR2
T29683DI0254Menopausal disorder[ICD-11: GA30]P29371TACR3
T77350DI0274Multiple myeloma[ICD-11: 2A83]P28062PSMB8
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T95302DI0005Acne vulgaris[ICD-11: ED80]P33032MC5R
T95302DI0371Sebaceous gland disorder[ICD-11: ED91]P33032MC5R
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T99816DI0062Breast cancer[ICD-11: 2C60-2C6Y]P30550GRPR
T99816DI0218Irritable bowel syndrome[ICD-11: DD91]P30550GRPR
T99816DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P30550GRPR
T87831DI0333Peptic ulcer[ICD-11: DA61]P21462FPR1
T25847DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P23284PPIB
T63083DI0048B-cell lymphoma[ICD-11: 2A86]Q06609RAD51
T63083DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q06609RAD51

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