Cucurbitacin P



Compound IDCDAMM02587
Common nameCucurbitacin P
IUPAC name17-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
Molecular formulaC30H48O7

Experimental data

Retention time12.67
Adduct[M+H]+
Actual mz521.344
Theoretical mz521.347
Error6.86
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.9698

Identifiers and class information

Inchi keyVVBWBGOEAVGFTN-MFJASQSZNA-N
SmilesO=C(CCC(O)(C)C)C(O)(C)C1C(O)CC2(C)C3CC=C4C(CC(O)C(O)C4(C)C)C3(C(=O)CC12C)C
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)10
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)520.705
Computed dipole moment(dipole)6.167
Total solvent accessible surface area (SASA)718.185
Hydrophobic component of SASA (FOSA)512.094
Hydrophilic component of SASA (FISA)191.483
Pie component of the SASA (PISA)14.607
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1532.33
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)10.6
Free energy of solvation of dipole (dip^2/V)0.0248195
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0330031
Globularity descriptor (glob)0.895015
Predicted polarizability in cubic angstroms (QPpolrz)48.888
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.787
Predicted octanol/gas partition coefficient (QPlogPoct)29.817
Predicted water/gas partition coefficient (QPlogPw)18.407
Predicted octanol/water partition coefficient (QPlogPo/w)2.786
Predicted aqueous solubility (QPlogS)-3.94
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.413
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.3
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)151.379
Predicted brain/blood partition coefficient (QPlogBB)-1.633
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)64.283
Predicted skin permeability, log Kp (QPlogKp)-4.037
PM3 calculated ionization potential (IP(ev))9.877
PM3 calculated electron affinity (EA(eV))-0.266
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)0.314
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)69.32
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)137.652
Number of nitrogen and oxygen atoms (#NandO)7
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
Q99720SIGMAR1Sigma opioid receptorT46360SwissTargetPrediction
Q4U2R8SLC22A6Solute carrier family 22 member 6 (by homology)T70680SwissTargetPrediction
P04054PLA2G1BPhospholipase A2 group 1BT31479SwissTargetPrediction
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
P10275ARAndrogen ReceptorT11211SwissTargetPrediction
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
P08235NR3C2Mineralocorticoid receptorT72168SwissTargetPrediction
P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
P06401PGRProgesterone receptorT22939SwissTargetPrediction
P08185SERPINA6Corticosteroid binding globulinT88452SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
Q9UHC9NPC1L1Niemann-Pick C1-like protein 1T33901SwissTargetPrediction
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P17706PTPN2T-cell protein-tyrosine phosphataseT49156SwissTargetPrediction
P14902IDO1Indoleamine 2,3-dioxygenaseT89697SwissTargetPrediction
Q07869PPARAPeroxisome proliferator-activated receptor alphaT86591SwissTargetPrediction
Q03181PPARDPeroxisome proliferator-activated receptor deltaT36557SwissTargetPrediction
P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
P11473VDRVitamin D receptorT34234SwissTargetPrediction
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
Q13133NR1H3LXR-alphaT52297SwissTargetPrediction
Q9UM73ALKALK tyrosine kinase receptorT56418SwissTargetPrediction
P42345MTORSerine/threonine-protein kinase mTORT75243SwissTargetPrediction
P36888FLT3Tyrosine-protein kinase receptor FLT3T74312SwissTargetPrediction
P11802CDK4Cyclin-dependent kinase 4T85799SwissTargetPrediction
P48147PREPProlyl endopeptidaseT86161SwissTargetPrediction
P51449RORCNuclear receptor ROR-gammaT25307SwissTargetPrediction
Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
P43116PTGER2Prostanoid EP2 receptorT38529SwissTargetPrediction
P49356FNTBFarnesyl protein transferaseT13127SwissTargetPrediction
P80365HSD11B211-beta-hydroxysteroid dehydrogenase 2T43721SwissTargetPrediction
P11413G6PDGlucose-6-phosphate 1-dehydrogenaseT63484SwissTargetPrediction
Q16850CYP51A1Cytochrome P450 51 (by homology)T32972SwissTargetPrediction
P05093CYP17A1Cytochrome P450 17A1T89041SwissTargetPrediction
P20701ITGALIntercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2T35640SwissTargetPrediction and SEA
Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
P35408PTGER4Prostanoid EP4 receptorT18876SwissTargetPrediction
P43115PTGER3Prostanoid EP3 receptorT85467SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
P34995PTGER1Prostanoid EP1 receptorT15497SwissTargetPrediction
Q13258PTGDRProstanoid DP receptorT68782SwissTargetPrediction
P43088PTGFRProstanoid FP receptorT75797SwissTargetPrediction
P35398RORANuclear receptor ROR-alphaT43206SwissTargetPrediction
P43119PTGIRProstanoid IP receptorT99954SwissTargetPrediction
Q15393SF3B3Splicing factor 3B subunit 3T96723SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T46360DI0105Cough[ICD-11: MD12]Q99720SIGMAR1
T70680DI0167Gout[ICD-11: FA25]Q4U2R8SLC22A6
T70680DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q4U2R8SLC22A6
T70680DI0310Ocular disease[ICD-11: N.A.]Q4U2R8SLC22A6
T31479DI0230Leishmaniasis[ICD-11: 1F54]P04054PLA2G1B
T31479DI0335Peroxisomal disease[ICD-11: 5C57]P04054PLA2G1B
T31479DI0367Rosacea[ICD-11: ED90]P04054PLA2G1B
T31479DI0398Synthesis disorder[ICD-11: 5C52-5C59]P04054PLA2G1B
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
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
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
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
T86591DI0187Hyperlipidemia[ICD-11: 5C80]Q07869PPARA
T86591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q07869PPARA
T86591DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q07869PPARA
T36557DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]Q03181PPARD
T36557DI0308Obesity[ICD-11: 5B80-5B81]Q03181PPARD
T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
T34234DI0083Chronic kidney disease[ICD-11: GB61]P11473VDR
T34234DI0171Hair/hair growth developmental defect[ICD-11: LC30]P11473VDR
T34234DI0189Hyper-parathyroidism[ICD-11: 5A51]P11473VDR
T34234DI0195Hypo-parathyroidism[ICD-11: 5A50]P11473VDR
T34234DI0266Mineral deficiency[ICD-11: 5B5K]P11473VDR
T34234DI0351Psoriasis[ICD-11: EA90]P11473VDR
T34234DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]P11473VDR
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T52297DI0117Depression[ICD-11: 6A70-6A7Z]Q13133NR1H3
T56418DI0238Lung cancer[ICD-11: 2C25]Q9UM73ALK
T56418DI0251Mature T-cell lymphoma[ICD-11: 2A90]Q9UM73ALK
T56418DI0303Non-small-cell lung cancer[ICD-11: 2C25]Q9UM73ALK
T75243DI0036Arteries/arterioles disorder[ICD-11: BD52]P42345MTOR
T75243DI0085Chronic myelomonocytic leukaemia[ICD-11: 2A40]P42345MTOR
T75243DI0274Multiple myeloma[ICD-11: 2A83]P42345MTOR
T75243DI0361Renal cell carcinoma[ICD-11: 2C90]P42345MTOR
T75243DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P42345MTOR
T75243DI0413Transplant rejection[ICD-11: NE84]P42345MTOR
T74312DI0012Acute myeloid leukaemia[ICD-11: 2A60]P36888FLT3
T74312DI0058Bone/articular cartilage neoplasm[ICD-11: 2F7B]P36888FLT3
T74312DI0095Colorectal cancer[ICD-11: 2B91]P36888FLT3
T74312DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P36888FLT3
T74312DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P36888FLT3
T74312DI0248Mastocytosis[ICD-11: 2A21]P36888FLT3
T74312DI0250Mature B-cell lymphoma[ICD-11: 2A85]P36888FLT3
T74312DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P36888FLT3
T85799DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11802CDK4
T85799DI0238Lung cancer[ICD-11: 2C25]P11802CDK4
T85799DI0351Psoriasis[ICD-11: EA90]P11802CDK4
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
T38529DI0003Abortion[ICD-11: JA00]P43116PTGER2
T38529DI0102Coronary atherosclerosis[ICD-11: BA52]P43116PTGER2
T38529DI0121Diabetic foot ulcer[ICD-11: BD54]P43116PTGER2
T38529DI0166Glaucoma[ICD-11: 9C61]P43116PTGER2
T38529DI0356Pulmonary hypertension[ICD-11: BB01]P43116PTGER2
T38529DI0378Sexual dysfunction[ICD-11: HA00-HA01]P43116PTGER2
T38529DI0413Transplant rejection[ICD-11: NE84]P43116PTGER2
T13127DI0342Premature ageing appearance[ICD-11: LD2B]P49356FNTB
T43721DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P80365HSD11B2
T63484DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P11413G6PD
T32972DI0209Infectious meningitis[ICD-11: 1D01]Q16850CYP51A1
T32972DI0289Nail/perionychium infection[ICD-11: EE12]Q16850CYP51A1
T32972DI0316Onchocerciasis[ICD-11: 1F6A]Q16850CYP51A1
T89041DI0346Prostate cancer[ICD-11: 2C82]P05093CYP17A1
T35640DI0351Psoriasis[ICD-11: EA90]P20701ITGAL
T35640DI0436Visual system disease[ICD-11: 9E1Z]P20701ITGAL
T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
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
T85467DI0166Glaucoma[ICD-11: 9C61]P43115PTGER3
T85467DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P43115PTGER3
T85467DI0414Transplanted organ/tissue[ICD-11: QB63]P43115PTGER3
T15497DI0405Thrombosis[ICD-11: DB61-GB90]P34995PTGER1
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T75797DI0003Abortion[ICD-11: JA00]P43088PTGFR
T75797DI0102Coronary atherosclerosis[ICD-11: BA52]P43088PTGFR
T75797DI0166Glaucoma[ICD-11: 9C61]P43088PTGFR
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
T96723DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q15393SF3B3
T96723DI0085Chronic myelomonocytic leukaemia[ICD-11: 2A40]Q15393SF3B3
T96723DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q15393SF3B3

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