Nomilinic acid



Compound IDCDAMM01284
Common nameNomilinic acid
IUPAC name3-acetyloxy-3-[11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.01,14.02,7]pentadecan-6-yl]propanoic acid
Molecular formulaC28H36O10

Experimental data

Retention time39.2
Adduct[M+H]+
Actual mz533.233
Theoretical mz533.238
Error10.46
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.3853

Identifiers and class information

Inchi keyZIKZPLSIAVHITA-UHFFFAOYNA-N
SmilesO=C(O)CC(OC(=O)C)C1(C)C(CC(=O)C2(C)C1CCC3(C)C(OC(=O)C4OC423)C5=COC=C5)C(O)(C)C
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

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)1
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)6
Number of reactive functional groups (#rtvFG)4
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)532.586
Computed dipole moment(dipole)11.928
Total solvent accessible surface area (SASA)676.068
Hydrophobic component of SASA (FOSA)368.828
Hydrophilic component of SASA (FISA)190.979
Pie component of the SASA (PISA)116.261
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1412.58
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)12.25
Free energy of solvation of dipole (dip^2/V)0.100722
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0256248
Globularity descriptor (glob)0.900571
Predicted polarizability in cubic angstroms (QPpolrz)47.635
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.861
Predicted octanol/gas partition coefficient (QPlogPoct)27.195
Predicted water/gas partition coefficient (QPlogPw)17.108
Predicted octanol/water partition coefficient (QPlogPo/w)2.412
Predicted aqueous solubility (QPlogS)-3.396
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.394
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.888
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)38.766
Predicted brain/blood partition coefficient (QPlogBB)-1.368
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)18.753
Predicted skin permeability, log Kp (QPlogKp)-4.054
PM3 calculated ionization potential (IP(ev))9.725
PM3 calculated electron affinity (EA(eV))0.003
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-0.232
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)56.54
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)167.138
Number of nitrogen and oxygen atoms (#NandO)10
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
P42336PIK3CAPI3-kinase p110-alpha subunitT80276SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P17706PTPN2T-cell protein-tyrosine phosphataseT49156SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P21731TBXA2RThromboxane A2 receptorT76198SwissTargetPrediction
P35372OPRM1Mu opioid receptorT47768SwissTargetPrediction
P41145OPRK1Kappa Opioid receptorT60693SwissTargetPrediction
P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P42575CASP2Caspase-2T09128SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
P23946CMA1ChymaseT05114SwissTargetPrediction
P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SwissTargetPrediction
Q9Y5Y4PTGDR2G protein-coupled receptor 44T61722SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P04035HMGCRHMG-CoA reductaseT53585SwissTargetPrediction
Q15722LTB4RLeukotriene B4 receptor 1T59626SwissTargetPrediction
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
P08238HSP90AB1Heat shock protein HSP 90-betaT96623SwissTargetPrediction
P32246CCR1C-C chemokine receptor type 1T16016SwissTargetPrediction
P01375TNFTNF-alphaT20178SwissTargetPrediction
P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
P53779MAPK10c-Jun N-terminal kinase 3T85421SwissTargetPrediction
P29466CASP1Caspase-1T98269SwissTargetPrediction
Q9UNA0ADAMTS5ADAMTS5T98896SwissTargetPrediction
P35408PTGER4Prostanoid EP4 receptorT18876SwissTargetPrediction
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
P23109AMPD1AMP deaminase 1T84553SwissTargetPrediction
P25101EDNRAEndothelin receptor ET-AT23499SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P42574CASP3Caspase-3T57943SwissTargetPrediction
P55210CASP7Caspase-7T72252SwissTargetPrediction
Q92793CREBBPCREB-binding protein/p53T03634SwissTargetPrediction
P24557TBXAS1Thromboxane-A synthaseT78356SwissTargetPrediction
P10619CTSALysosomal protective proteinT37154SwissTargetPrediction
O43174CYP26A1Cytochrome P450 26A1T84634SwissTargetPrediction
P32239CCKBRCholecystokinin B receptor (by homology)T05849SwissTargetPrediction
Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
P55212CASP6Caspase-6T20600SwissTargetPrediction
Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
P43119PTGIRProstanoid IP receptorT99954SwissTargetPrediction
Q96GD4AURKBSerine/threonine-protein kinase Aurora-BT46781SwissTargetPrediction
P24530EDNRBEndothelin receptor ET-BT92828SwissTargetPrediction
Q16647PTGISProstaglandin I2 synthaseT83979SwissTargetPrediction
P23109AMPD1AMP deaminase 1T84553SwissTargetPrediction
P26010ITGB7Integrin alpha-4/beta-7T07403SwissTargetPrediction
P09238MMP10Matrix metalloproteinase 10T40488SwissTargetPrediction
P01584IL1BInterleukin-1 betaT42000SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T80276DI0062Breast cancer[ICD-11: 2C60-2C6Y]P42336PIK3CA
T80276DI0151Follicular lymphoma[ICD-11: 2A80]P42336PIK3CA
T80276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P42336PIK3CA
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
T40016DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P04150NR3C1
T40016DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P04150NR3C1
T40016DI0037Asthma[ICD-11: CA23]P04150NR3C1
T40016DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P04150NR3C1
T40016DI0108Cushing syndrome[ICD-11: 5A70]P04150NR3C1
T40016DI0280Muscular dystrophy[ICD-11: 8C70]P04150NR3C1
T40016DI0314Oesophagitis[ICD-11: DA24]P04150NR3C1
T40016DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P04150NR3C1
T40016DI0366Rheumatoid arthritis[ICD-11: FA20]P04150NR3C1
T40016DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04150NR3C1
T40016DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P04150NR3C1
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
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
T76198DI0102Coronary atherosclerosis[ICD-11: BA52]P21731TBXA2R
T76198DI0121Diabetic foot ulcer[ICD-11: BD54]P21731TBXA2R
T76198DI0287Myocardial infarction[ICD-11: BA41-BA43]P21731TBXA2R
T76198DI0378Sexual dysfunction[ICD-11: HA00-HA01]P21731TBXA2R
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
T60693DI0304Non-specific cutaneous vascular symptom[ICD-11: ME64]P41145OPRK1
T60693DI0324Pain[ICD-11: MG30-MG3Z]P41145OPRK1
T60693DI0349Pruritus[ICD-11: EC90]P41145OPRK1
T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
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
T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
T61722DI0102Coronary atherosclerosis[ICD-11: BA52]Q9Y5Y4PTGDR2
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T53585DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P04035HMGCR
T53585DI0102Coronary atherosclerosis[ICD-11: BA52]P04035HMGCR
T53585DI0128Dyslipidemia[ICD-11: 5C80-5C81]P04035HMGCR
T53585DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P04035HMGCR
T53585DI0275Multiple sclerosis[ICD-11: 8A40]P04035HMGCR
T53585DI0287Myocardial infarction[ICD-11: BA41-BA43]P04035HMGCR
T53585DI0324Pain[ICD-11: MG30-MG3Z]P04035HMGCR
T59626DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]Q15722LTB4R
T59626DI0355Pulmonary disease[ICD-11: 1B10-1F85]Q15722LTB4R
T59626DI0361Renal cell carcinoma[ICD-11: 2C90]Q15722LTB4R
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T96623DI0062Breast cancer[ICD-11: 2C60-2C6Y]P08238HSP90AB1
T96623DI0238Lung cancer[ICD-11: 2C25]P08238HSP90AB1
T96623DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P08238HSP90AB1
T96623DI0249Mature B-cell leukaemia[ICD-11: 2A82]P08238HSP90AB1
T96623DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P08238HSP90AB1
T96623DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P08238HSP90AB1
T96623DI0395Stomach cancer[ICD-11: 2B72]P08238HSP90AB1
T16016DI0120Diabetes mellitus[ICD-11: 5A10]P32246CCR1
T16016DI0366Rheumatoid arthritis[ICD-11: FA20]P32246CCR1
T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
T74456DI0137Essential hypertension[ICD-11: BA00]P30556AGTR1
T74456DI0190Hypertension[ICD-11: BA00-BA04]P30556AGTR1
T74456DI0373Secondary hypertension[ICD-11: BA04]P30556AGTR1
T74456DI0425Urinary system clinical symptom[ICD-11: MF8Y]P30556AGTR1
T85421DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]P53779MAPK10
T98269DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P29466CASP1
T98269DI0146Fibrosis[ICD-11: GA14-GC01]P29466CASP1
T98269DI0366Rheumatoid arthritis[ICD-11: FA20]P29466CASP1
T98269DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P29466CASP1
T98896DI0320Osteoarthritis[ICD-11: FA00-FA05]Q9UNA0ADAMTS5
T18876DI0037Asthma[ICD-11: CA23]P35408PTGER4
T18876DI0175Heart failure[ICD-11: BD10-BD1Z]P35408PTGER4
T18876DI0264Migraine[ICD-11: 8A80]P35408PTGER4
T18876DI0303Non-small-cell lung cancer[ICD-11: 2C25]P35408PTGER4
T18876DI0324Pain[ICD-11: MG30-MG3Z]P35408PTGER4
T18876DI0360Rectum cancer[ICD-11: 2B92]P35408PTGER4
T18876DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35408PTGER4
T18876DI0414Transplanted organ/tissue[ICD-11: QB63]P35408PTGER4
T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
T03634DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q92793CREBBP
T03634DI0346Prostate cancer[ICD-11: 2C82]Q92793CREBBP
T03634DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92793CREBBP
T03634DI0399Systemic sclerosis[ICD-11: 4A42]Q92793CREBBP
T78356DI0030Angina pectoris[ICD-11: BA40]P24557TBXAS1
T37154DI0009Acute diabete complication[ICD-11: 5A2Y]P10619CTSA
T84634DI0314Oesophagitis[ICD-11: DA24]O43174CYP26A1
T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
T15700DI0120Diabetes mellitus[ICD-11: 5A10]Q9UQ81MCH5
T15700DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQ81MCH5
T99954DI0003Abortion[ICD-11: JA00]P43119PTGIR
T99954DI0102Coronary atherosclerosis[ICD-11: BA52]P43119PTGIR
T99954DI0356Pulmonary hypertension[ICD-11: BB01]P43119PTGIR
T46781DI0009Acute diabete complication[ICD-11: 5A2Y]Q96GD4AURKB
T46781DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q96GD4AURKB
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
T42000DI0267Mineral excesses[ICD-11: 5B91]P01584IL1B
T42000DI0269Monogenic autoinflammatory syndrome[ICD-11: 4A60]P01584IL1B
T42000DI0320Osteoarthritis[ICD-11: FA00-FA05]P01584IL1B
T42000DI0366Rheumatoid arthritis[ICD-11: FA20]P01584IL1B

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