Macamide



Compound IDCDAMM01744
Common nameMacamide
IUPAC nameN-benzyl-5-oxooctadeca-6,8-dienamide
Molecular formulaC25H37NO2

Experimental data

Retention time11.47
Adduct[M+K]+
Actual mz422.244
Theoretical mz422.245
Error2.03
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.8889

Identifiers and class information

Inchi keyDKMGVACNAAKVRR-MRBSYODNSA-N
SmilesO=C(C=CC=CCCCCCCCCC)CCCC(=O)NCC=1C=CC=CC1
SuperclassLipids and lipid-like molecules
ClassFatty Acyls

Pharmacokinetic properties

Number of descriptor values(#stars)3
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)17
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)383.573
Computed dipole moment(dipole)8.608
Total solvent accessible surface area (SASA)889.168
Hydrophobic component of SASA (FOSA)575.711
Hydrophilic component of SASA (FISA)82.679
Pie component of the SASA (PISA)230.778
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1535.71
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)4.5
Free energy of solvation of dipole (dip^2/V)0.0482501
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0050609
Globularity descriptor (glob)0.723971
Predicted polarizability in cubic angstroms (QPpolrz)46.593
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.546
Predicted octanol/gas partition coefficient (QPlogPoct)18.961
Predicted water/gas partition coefficient (QPlogPw)7.617
Predicted octanol/water partition coefficient (QPlogPo/w)6.12
Predicted aqueous solubility (QPlogS)-7.386
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.932
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.725
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1129.34
Predicted brain/blood partition coefficient (QPlogBB)-1.513
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)838.185
Predicted skin permeability, log Kp (QPlogKp)-0.598
PM3 calculated ionization potential (IP(ev))9.604
PM3 calculated electron affinity (EA(eV))0.534
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)0.864
Predicted qualitative human oral absorption (HumanOralAbsorption)1
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)19.978
Van der Waals surface area (PSA)65.118
Number of nitrogen and oxygen atoms (#NandO)3
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
O15379HDAC3Histone deacetylase 3T05090SEA
P14555PLA2G2APhospholipase A2 group IIAT19160SEA
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SEA
P21554CNR1Cannabinoid receptor 1 (by homology)T76685SEA
P34913EPHX2Epoxide hydrataseT35734SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P22748CA4Carbonic anhydrase IVT53378SEA
Q8WUI4HDAC7Histone deacetylase 7T98698SEA
Q9UKV0HDAC9Histone deacetylase 9T03687SEA
Q92769HDAC2Histone deacetylase 2T51191SEA
P23141CES1Acyl coenzyme A:cholesterol acyltransferaseT76369SEA
O00519FAAHAnandamide amidohydrolaseT11754SEA
Q8NER1TRPV1Vanilloid receptorT83193SEA
Q07869PPARAPeroxisome proliferator-activated receptor alphaT86591SEA
P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
P06746POLBDNA polymerase beta (by homology)T06958SEA
P08253MMP2Matrix metalloproteinase 2T68251SEA
P22894MMP8Matrix metalloproteinase 8T08856SEA
P08254MMP3Matrix metalloproteinase 3T86702SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03956MMP1Matrix metalloproteinase 1T52450SEA
P17655CAPN2Calpain 2T86837SEA
P06276BCHEButyrylcholinesteraseT99799SEA
P09237MMP7Matrix metalloproteinase 7T73475SEA
P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SEA
Q99685MGLLMonoglyceride lipaseT18664SEA
Q02156PRKCEProtein kinase C epsilonT00895SEA
P48039MTNR1AMelatonin receptor 1AT97613SEA
P49286MTNR1BMelatonin receptor 1BT48268SEA
P34972CNR2Cannabinoid receptor 2T37693SEA
P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
Q8TDS5OXER1Oxoeicosanoid receptor 1T68834SEA
P16109SELPP-selectinT10965SEA
Q9Y4D2DAGLASn1-specific diacylglycerol lipase alphaT03150SEA
Q16549PCSK7Subtilisin/kexin type 7T33211SEA
P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
Q15661TPSAB1Tryptase beta-1T14558SEA
O43497CACNA1GVoltage-gated T-type calcium channel alpha-1G subunitT64795SEA
Q9NYK1TLR7Toll-like receptor (TLR7/TLR9)T46482SEA
Q13822ENPP2AutotaxinT63512SEA
Q9HBW0LPAR2Lysophosphatidic acid receptor Edg-4T39380SEA
P28336NMBRNeuromedin B receptorT68887SEA
P10826RARBRetinoic acid receptor betaT61657SEA
Q96DB2HDAC11Histone deacetylase 11T97903SEA
O75908SOAT2Acyl coenzyme A:cholesterol acyltransferase 2T14463SEA
O94759TRPM2Transient receptor potential cation channel subfamily M member 2T78205SEA
Q969S8HDAC10Histone deacetylase 10T94324SEA
O95136S1PR2Sphingosine 1-phosphate receptor Edg-5T47888SEA
Q9H2K8TAOK3Serine/threonine-protein kinase TAO3T63682SEA
Q7L7X3TAOK1Serine/threonine-protein kinase TAO1T97016SEA
O60906SMPD2Neutral sphingomyelinaseT57316SEA
Q9UBY5LPAR3Lysophosphatidic acid receptor Edg-7T95923SEA
Q92633LPAR1Lysophosphatidic acid receptor Edg-2T92640SEA
P23284PPIBCyclophilin BT25847SEA
Q9UJM8HAO1Hydroxyacid oxidase 1T63170SEA
P09668CTSHCathepsin (H and K)T40103SEA
Q9UP65PLA2G4CCytosolic phospholipase A2 gammaT91113SEA
P29120PCSK1Neuroendocrine convertase 1T36445SEA
Q92824PCSK5Proprotein convertase subtilisin/kexin type 5T38581SEA
Q9BY41HDAC8Histone deacetylase 8T28887SEA
Q9Y4G9PCSK6Proprotein convertase subtilisin/kexin type 6T86503SEA
P51843NR0B1Orphan nuclear receptor DAX-1T23191SEA
O60603TLR2Toll-like receptor 2T82078SEA
P47870GABRB2GABA(A) receptor beta-2T80387SEA
P16519PCSK2Neuroendocrine convertase 2T97749SEA
Q9BXA5SUCNR1Succinate receptorT70633SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T05090DI0241Lymphoma[ICD-11: 2A80-2A86]O15379HDAC3
T05090DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O15379HDAC3
T19160DI0062Breast cancer[ICD-11: 2C60-2C6Y]P14555PLA2G2A
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T76685DI0031Anorexia nervosa[ICD-11: 6B80]P21554CNR1
T76685DI0214Insomnia[ICD-11: 7A00-7A0Z]P21554CNR1
T76685DI0308Obesity[ICD-11: 5B80-5B81]P21554CNR1
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
T76369DI0335Peroxisomal disease[ICD-11: 5C57]P23141CES1
T76369DI0398Synthesis disorder[ICD-11: 5C52-5C59]P23141CES1
T11754DI0101Corneal disease[ICD-11: 9A76-9A78]O00519FAAH
T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
T86591DI0187Hyperlipidemia[ICD-11: 5C80]Q07869PPARA
T86591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q07869PPARA
T86591DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q07869PPARA
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
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
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
T18664DI0163General pain disorder[ICD-11: 8E43]Q99685MGLL
T18664DI0409Tic disorder[ICD-11: 8A05]Q99685MGLL
T00895DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]Q02156PRKCE
T00895DI0243Malaria[ICD-11: 1F40-1F45]Q02156PRKCE
T97613DI0214Insomnia[ICD-11: 7A00-7A0Z]P48039MTNR1A
T48268DI0214Insomnia[ICD-11: 7A00-7A0Z]P49286MTNR1B
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
T14558DI0155Fungal infection[ICD-11: 1F29-1F2F]Q15661TPSAB1
T14558DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q15661TPSAB1
T64795DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]O43497CACNA1G
T64795DI0190Hypertension[ICD-11: BA00-BA04]O43497CACNA1G
T64795DI0276Multiple structural anomalies syndrome[ICD-11: LD2F]O43497CACNA1G
T64795DI0326Pancreatic cancer[ICD-11: 2C10]O43497CACNA1G
T64795DI0370Schizophrenia[ICD-11: 6A20]O43497CACNA1G
T46482DI0243Malaria[ICD-11: 1F40-1F45]Q9NYK1TLR7
T46482DI0384Skin disease[ICD-11: EA00-EM0Z]Q9NYK1TLR7
T63512DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q13822ENPP2
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T61657DI0225Kaposi sarcoma[ICD-11: 2B57]P10826RARB
T14463DI0017Adrenal cancer[ICD-11: 2D11]O75908SOAT2
T94324DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q969S8HDAC10
T47888DI0419Ulcerative colitis[ICD-11: DD71]O95136S1PR2
T95923DI0146Fibrosis[ICD-11: GA14-GC01]Q9UBY5LPAR3
T95923DI0399Systemic sclerosis[ICD-11: 4A42]Q9UBY5LPAR3
T92640DI0146Fibrosis[ICD-11: GA14-GC01]Q92633LPAR1
T92640DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q92633LPAR1
T92640DI0351Psoriasis[ICD-11: EA90]Q92633LPAR1
T92640DI0399Systemic sclerosis[ICD-11: 4A42]Q92633LPAR1
T25847DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P23284PPIB
T63170DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]Q9UJM8HAO1
T28887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9BY41HDAC8
T82078DI0346Prostate cancer[ICD-11: 2C82]O60603TLR2
T80387DI0117Depression[ICD-11: 6A70-6A7Z]P47870GABRB2
T80387DI0214Insomnia[ICD-11: 7A00-7A0Z]P47870GABRB2
T80387DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P47870GABRB2
T80387DI0411Tonus and reflex abnormality[ICD-11: MB47]P47870GABRB2

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