Perillic acid



Compound IDCDAMM02077
Common namePerillic acid
IUPAC name4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
Molecular formulaC10H14O2

Experimental data

Retention time7.63
Adduct[M+Na]+
Actual mz189.09
Theoretical mz189.088
Error7.31
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.8464

Identifiers and class information

Inchi keyCDSMSBUVCWHORP-UHFFFAOYNA-N
SmilesO=C(O)C1=CCC(C(=C)C)CC1
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

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)2
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)166.219
Computed dipole moment(dipole)6.149
Total solvent accessible surface area (SASA)399.669
Hydrophobic component of SASA (FOSA)232.902
Hydrophilic component of SASA (FISA)104.227
Pie component of the SASA (PISA)62.54
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)648.167
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)2
Free energy of solvation of dipole (dip^2/V)0.0583284
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0050041
Globularity descriptor (glob)0.906266
Predicted polarizability in cubic angstroms (QPpolrz)19.099
Predicted hexadecane/gas partition coefficient (QPlogPC16)5.736
Predicted octanol/gas partition coefficient (QPlogPoct)8.974
Predicted water/gas partition coefficient (QPlogPw)4.809
Predicted octanol/water partition coefficient (QPlogPo/w)2.339
Predicted aqueous solubility (QPlogS)-2.517
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.865
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.539
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)257.701
Predicted brain/blood partition coefficient (QPlogBB)-0.403
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)145.303
Predicted skin permeability, log Kp (QPlogKp)-3.028
PM3 calculated ionization potential (IP(ev))10.051
PM3 calculated electron affinity (EA(eV))0.123
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)-0.249
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)83.798
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)50.085
Number of nitrogen and oxygen atoms (#NandO)2
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
P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
Q99720SIGMAR1Sigma opioid receptorT46360SwissTargetPrediction
P24046GABRR1GABA receptor rho-1 subunitT99665SEA
P04181OATOrnithine aminotransferase, mitochondrialT62073SwissTargetPrediction and SEA
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P04054PLA2G1BPhospholipase A2 group 1BT31479SwissTargetPrediction
P31213SRD5A2Steroid 5-alpha-reductase 2T71390SwissTargetPrediction
P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
Q01959SLC6A3Dopamine transporterT55959SwissTargetPrediction
P23141CES1Acyl coenzyme A:cholesterol acyltransferaseT76369SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
P10275ARAndrogen ReceptorT11211SwissTargetPrediction
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
O15229KMOKynurenine 3-monooxygenaseT50973SwissTargetPrediction
O00519FAAHAnandamide amidohydrolaseT11754SwissTargetPrediction
P08235NR3C2Mineralocorticoid receptorT72168SwissTargetPrediction
P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
P06401PGRProgesterone receptorT22939SwissTargetPrediction
P08185SERPINA6Corticosteroid binding globulinT88452SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
Q9UHC9NPC1L1Niemann-Pick C1-like protein 1T33901SwissTargetPrediction
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P29350PTPN6Protein-tyrosine phosphatase 1CT98264SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P17706PTPN2T-cell protein-tyrosine phosphataseT49156SwissTargetPrediction
P14902IDO1Indoleamine 2,3-dioxygenaseT89697SwissTargetPrediction
Q01469FABP5Fatty acid binding protein epidermalT21507SwissTargetPrediction
Q03181PPARDPeroxisome proliferator-activated receptor deltaT36557SwissTargetPrediction
O14842FFAR1Free fatty acid receptor 1T25608SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
Q13133NR1H3LXR-alphaT52297SwissTargetPrediction
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
O00767SCDAcyl-CoA desaturaseT10897SwissTargetPrediction
P48147PREPProlyl endopeptidaseT86161SwissTargetPrediction
P51449RORCNuclear receptor ROR-gammaT25307SwissTargetPrediction
Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P24723PRKCHProtein kinase C etaT40149SwissTargetPrediction
P80365HSD11B211-beta-hydroxysteroid dehydrogenase 2T43721SwissTargetPrediction
Q06124PTPN11Protein-tyrosine phosphatase 2CT13057SwissTargetPrediction
Q15722LTB4RLeukotriene B4 receptor 1T59626SwissTargetPrediction
P05093CYP17A1Cytochrome P450 17A1T89041SwissTargetPrediction
P11137MAP2Microtubule-associated protein 2T23276SwissTargetPrediction
P11387TOP1DNA topoisomerase IT09826SwissTargetPrediction
P01375TNFTNF-alphaT20178SwissTargetPrediction
P35408PTGER4Prostanoid EP4 receptorT18876SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
P34995PTGER1Prostanoid EP1 receptorT15497SwissTargetPrediction
P43088PTGFRProstanoid FP receptorT75797SwissTargetPrediction
Q9NQR1KMT5AN-lysine methyltransferase SETD8T30420SwissTargetPrediction
P35398RORANuclear receptor ROR-alphaT43206SwissTargetPrediction
P43119PTGIRProstanoid IP receptorT99954SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T02703DI0083Chronic kidney disease[ICD-11: GB61]P35228NOS2
T02703DI0320Osteoarthritis[ICD-11: FA00-FA05]P35228NOS2
T02703DI0375Sepsis[ICD-11: 1G40-1G41]P35228NOS2
T02703DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35228NOS2
T46360DI0105Cough[ICD-11: MD12]Q99720SIGMAR1
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T31479DI0230Leishmaniasis[ICD-11: 1F54]P04054PLA2G1B
T31479DI0335Peroxisomal disease[ICD-11: 5C57]P04054PLA2G1B
T31479DI0367Rosacea[ICD-11: ED90]P04054PLA2G1B
T31479DI0398Synthesis disorder[ICD-11: 5C52-5C59]P04054PLA2G1B
T71390DI0348Prostate hyperplasia[ICD-11: GA90]P31213SRD5A2
T27812DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P31645SLC6A4
T27812DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P31645SLC6A4
T27812DI0087Chronic pain[ICD-11: MG30]P31645SLC6A4
T27812DI0096concerning food/fluid intake symptom[ICD-11: MG43]P31645SLC6A4
T27812DI0101Corneal disease[ICD-11: 9A76-9A78]P31645SLC6A4
T27812DI0105Cough[ICD-11: MD12]P31645SLC6A4
T27812DI0117Depression[ICD-11: 6A70-6A7Z]P31645SLC6A4
T27812DI0264Migraine[ICD-11: 8A80]P31645SLC6A4
T27812DI0301Nicotine use disorder[ICD-11: 6C4A]P31645SLC6A4
T27812DI0308Obesity[ICD-11: 5B80-5B81]P31645SLC6A4
T27812DI0324Pain[ICD-11: MG30-MG3Z]P31645SLC6A4
T55959DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q01959SLC6A3
T55959DI0051Bipolar disorder[ICD-11: 6A60]Q01959SLC6A3
T55959DI0101Corneal disease[ICD-11: 9A76-9A78]Q01959SLC6A3
T55959DI0290Narcolepsy[ICD-11: 7A20]Q01959SLC6A3
T55959DI0308Obesity[ICD-11: 5B80-5B81]Q01959SLC6A3
T55959DI0331Parkinsonism[ICD-11: 8A00]Q01959SLC6A3
T76369DI0335Peroxisomal disease[ICD-11: 5C57]P23141CES1
T76369DI0398Synthesis disorder[ICD-11: 5C52-5C59]P23141CES1
T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
T11211DI0005Acne vulgaris[ICD-11: ED80]P10275AR
T11211DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10275AR
T11211DI0021Alcoholic liver disease[ICD-11: DB94]P10275AR
T11211DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10275AR
T11211DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P10275AR
T11211DI0145Female pelvic pain[ICD-11: GA34]P10275AR
T11211DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P10275AR
T11211DI0237Low bone mass disorder[ICD-11: FB83]P10275AR
T11211DI0247Mammary tumour[ICD-11: 2C60-2C6Z]P10275AR
T11211DI0346Prostate cancer[ICD-11: 2C82]P10275AR
T11211DI0401Testicular dysfunction[ICD-11: 5A81]P10275AR
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
T11754DI0101Corneal disease[ICD-11: 9A76-9A78]O00519FAAH
T72168DI0018Adrenocortical insufficiency[ICD-11: 5A74]P08235NR3C2
T72168DI0083Chronic kidney disease[ICD-11: GB61]P08235NR3C2
T72168DI0100Contraceptive management[ICD-11: QA21]P08235NR3C2
T72168DI0175Heart failure[ICD-11: BD10-BD1Z]P08235NR3C2
T72168DI0190Hypertension[ICD-11: BA00-BA04]P08235NR3C2
T72168DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P08235NR3C2
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
T22939DI0062Breast cancer[ICD-11: 2C60-2C6Y]P06401PGR
T22939DI0100Contraceptive management[ICD-11: QA21]P06401PGR
T22939DI0255Menstrual cycle bleeding disorder[ICD-11: GA20]P06401PGR
T22939DI0344Preterm labour/delivery[ICD-11: JB00]P06401PGR
T22939DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06401PGR
T88452DI0037Asthma[ICD-11: CA23]P08185SERPINA6
T88452DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P08185SERPINA6
T88452DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08185SERPINA6
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T33901DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q9UHC9NPC1L1
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
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
T89697DI0117Depression[ICD-11: 6A70-6A7Z]P14902IDO1
T36557DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]Q03181PPARD
T36557DI0308Obesity[ICD-11: 5B80-5B81]Q03181PPARD
T25608DI0417Type 2 diabetes mellitus[ICD-11: 5A11]O14842FFAR1
T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T52297DI0117Depression[ICD-11: 6A70-6A7Z]Q13133NR1H3
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T10897DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O00767SCD
T86161DI0092Coeliac disease[ICD-11: DA95]P48147PREP
T86161DI0210Influenza[ICD-11: 1E30-1E32]P48147PREP
T86161DI0238Lung cancer[ICD-11: 2C25]P48147PREP
T86161DI0265Mild neurocognitive disorder[ICD-11: 6D71]P48147PREP
T25307DI0042Autoimmune disease[ICD-11: 4A40-4A45]P51449RORC
T25307DI0107Crohn disease[ICD-11: DD70]P51449RORC
T25307DI0238Lung cancer[ICD-11: 2C25]P51449RORC
T25307DI0275Multiple sclerosis[ICD-11: 8A40]P51449RORC
T25307DI0351Psoriasis[ICD-11: EA90]P51449RORC
T25307DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P51449RORC
T02001DI0411Tonus and reflex abnormality[ICD-11: MB47]Q08499PDE4D
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T40149DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P24723PRKCH
T43721DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P80365HSD11B2
T13057DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q06124PTPN11
T59626DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]Q15722LTB4R
T59626DI0355Pulmonary disease[ICD-11: 1B10-1F85]Q15722LTB4R
T59626DI0361Renal cell carcinoma[ICD-11: 2C90]Q15722LTB4R
T89041DI0346Prostate cancer[ICD-11: 2C82]P05093CYP17A1
T23276DI0036Arteries/arterioles disorder[ICD-11: BD52]P11137MAP2
T23276DI0252Melanoma[ICD-11: 2C30]P11137MAP2
T23276DI0326Pancreatic cancer[ICD-11: 2C10]P11137MAP2
T23276DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11137MAP2
T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
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
T15497DI0405Thrombosis[ICD-11: DB61-GB90]P34995PTGER1
T75797DI0003Abortion[ICD-11: JA00]P43088PTGFR
T75797DI0102Coronary atherosclerosis[ICD-11: BA52]P43088PTGFR
T75797DI0166Glaucoma[ICD-11: 9C61]P43088PTGFR
T30420DI0235Liver cancer[ICD-11: 2C12]Q9NQR1KMT5A
T30420DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9NQR1KMT5A
T43206DI0235Liver cancer[ICD-11: 2C12]P35398RORA
T43206DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P35398RORA
T99954DI0003Abortion[ICD-11: JA00]P43119PTGIR
T99954DI0102Coronary atherosclerosis[ICD-11: BA52]P43119PTGIR
T99954DI0356Pulmonary hypertension[ICD-11: BB01]P43119PTGIR

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