N-(1-hydroxy-3-methylbutan-2-yl)-3-(2-oxo-2H-chromen-3-yl)benzamide



Compound IDCDAMM00148
Common nameN-(1-hydroxy-3-methylbutan-2-yl)-3-(2-oxo-2H-chromen-3-yl)benzamide
IUPAC nameN-[(2S)-1-hydroxy-3-methylbutan-2-yl]-3-(2-oxochromen-3-yl)benzamide
Molecular formulaC21H21NO4

Experimental data

Retention time50.14
Adduct[M+H]+
Actual mz352.155
Theoretical mz352.154
Error0.48
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2518

Identifiers and class information

Inchi keyPGLZOOJMIWATHH-UHFFFAOYSA-N
SmilesCC(C)C(CO)NC(=O)C1=CC=CC(=C1)C2=CC3=CC=CC=C3OC2=O
SuperclassPhenylpropanoids and polyketides
ClassIsoflavonoids

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)0
Number of rotatable bonds (#rotor)6
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)351.401
Computed dipole moment(dipole)3.592
Total solvent accessible surface area (SASA)652.193
Hydrophobic component of SASA (FOSA)192.592
Hydrophilic component of SASA (FISA)133.049
Pie component of the SASA (PISA)326.553
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1149.13
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)6.7
Free energy of solvation of dipole (dip^2/V)0.0112287
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0145283
Globularity descriptor (glob)0.813521
Predicted polarizability in cubic angstroms (QPpolrz)39.1
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.581
Predicted octanol/gas partition coefficient (QPlogPoct)19.587
Predicted water/gas partition coefficient (QPlogPw)12.62
Predicted octanol/water partition coefficient (QPlogPo/w)3.035
Predicted aqueous solubility (QPlogS)-4.74
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.636
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.107
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)542.249
Predicted brain/blood partition coefficient (QPlogBB)-1.138
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)255.3
Predicted skin permeability, log Kp (QPlogKp)-2.245
PM3 calculated ionization potential (IP(ev))9.231
PM3 calculated electron affinity (EA(eV))1.064
Number of likely metabolic reactions (#metab)1
Prediction of binding to human serum albumin (QPlogKhsa)0.167
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)93.655
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)93.701
Number of nitrogen and oxygen atoms (#NandO)5
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
P22303ACHEAcetylcholinesteraseT30082SEA
P21397MAOAMonoamine oxidase AT83875SEA
Q8IXJ6SIRT2NAD-dependent deacetylase sirtuin 2T83904SEA
P27338MAOBMonoamine oxidase BT83011SEA
P43235CTSKCathepsin KT11388SEA
P56817BACE1Beta-secretase 1T79031SEA
P07711CTSLCathepsin LT98691SEA
P07858CTSBCathepsin (B and K)T61746SEA
P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SEA
O14746TERTTelomerase reverse transcriptaseT86052SEA
P08842STSSteryl-sulfataseT33489SEA
P25774CTSSCathepsin ST68290SEA
Q14654KCNJ11Sulfonylurea receptor 2, Kir6.2T00820SEA
Q9UKP6UTS2RUrotensin II receptorT49072SEA
Q13526PIN1Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1T16308SEA
P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
O75173ADAMTS4ADAMTS4T79570SEA
O60911CTSVCathepsin (V and K)T93653SEA
Q15139PRKD1Protein kinase C muT47885SEA
Q8NET8TRPV3Transient receptor potential cation channel subfamily V member 3T58496SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q6DWJ6GPR139Probable G-protein coupled receptor 139T84439SEA
P40306PSMB1026S proteosomeT09022SEA
P22888LHCGRLuteinizing hormone/Choriogonadotropin receptorT79473SEA
P27169PON1Serum paraoxonase/arylesterase 1T34562SEA
Q9P0U3SENP1Sentrin-specific protease 1T96435SEA
P00748F12Coagulation factor XIIT38509SEA
Q7RTX1TAS1R1Taste receptorT41263SEA
Q9HAN5TRP1Cationic trypsinogenT27602SEA
P25786PSMA1Core proteasome 20S complexT61997SEA
P28072PSMB6Proteasome beta-1T54973SEA
Q99436PSMB7Proteasome beta-2T55986SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
T83904DI0365Retinopathy[ICD-11: 9B71]Q8IXJ6SIRT2
T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
T11388DI0237Low bone mass disorder[ICD-11: FB83]P43235CTSK
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
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
T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T33489DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P08842STS
T68290DI0042Autoimmune disease[ICD-11: 4A40-4A45]P25774CTSS
T68290DI0092Coeliac disease[ICD-11: DA95]P25774CTSS
T68290DI0107Crohn disease[ICD-11: DD70]P25774CTSS
T68290DI0120Diabetes mellitus[ICD-11: 5A10]P25774CTSS
T68290DI0163General pain disorder[ICD-11: 8E43]P25774CTSS
T68290DI0324Pain[ICD-11: MG30-MG3Z]P25774CTSS
T68290DI0382Sjogren syndrome[ICD-11: 4A43]P25774CTSS
T49072DI0037Asthma[ICD-11: CA23]Q9UKP6UTS2R
T16308DI0238Lung cancer[ICD-11: 2C25]Q13526PIN1
T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
T47885DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q15139PRKD1
T47885DI0426Urinary system disease[ICD-11: GC2Z]Q15139PRKD1
T58496DI0324Pain[ICD-11: MG30-MG3Z]Q8NET8TRPV3
T84439DI0377Sex development malformative disorder[ICD-11: LD2A]Q6DWJ6GPR139
T79473DI0144Female infertility[ICD-11: GA31]P22888LHCGR
T79473DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P22888LHCGR
T38509DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P00748F12
T41263DI0078Cholera[ICD-11: 1A00]Q7RTX1TAS1R1
T27602DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9HAN5TRP1
T27602DI0274Multiple myeloma[ICD-11: 2A83]Q9HAN5TRP1

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