3-Oxo-12,18-ursadien-28-oic acid



Compound IDCDAMM01900
Common name3-Oxo-12,18-ursadien-28-oic acid
IUPAC name1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-2,3,4,5,6,6a,7,8,8a,11,12,13-dodecahydropicene-4a-carboxylic acid
Molecular formulaC30H44O3

Experimental data

Retention time4.06
Adduct[M+H]+
Actual mz453.335
Theoretical mz453.336
Error3.92
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.1394

Identifiers and class information

Inchi keySHLWEZVZPAYIHX-UHFFFAOYNA-N
SmilesO=C(O)C12C(C3=CCC4C5(C)CCC(=O)C(C)(C)C5CCC4(C)C3(C)CC1)=C(C)C(C)CC2
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Plant source

  • Curcuma longa L.

    • 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)1
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)1
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-1
    Molecular weight (mol_MW)452.676
    Computed dipole moment(dipole)9.907
    Total solvent accessible surface area (SASA)694.237
    Hydrophobic component of SASA (FOSA)583.312
    Hydrophilic component of SASA (FISA)101.827
    Pie component of the SASA (PISA)9.098
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1394.72
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)4
    Free energy of solvation of dipole (dip^2/V)0.0703741
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0057617
    Globularity descriptor (glob)0.869592
    Predicted polarizability in cubic angstroms (QPpolrz)49.108
    Predicted hexadecane/gas partition coefficient (QPlogPC16)12.089
    Predicted octanol/gas partition coefficient (QPlogPoct)20.809
    Predicted water/gas partition coefficient (QPlogPw)7.329
    Predicted octanol/water partition coefficient (QPlogPo/w)6.224
    Predicted aqueous solubility (QPlogS)-7.29
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.059
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.878
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)271.565
    Predicted brain/blood partition coefficient (QPlogBB)-0.395
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)153.77
    Predicted skin permeability, log Kp (QPlogKp)-3.268
    PM3 calculated ionization potential (IP(ev))9.547
    PM3 calculated electron affinity (EA(eV))-0.05
    Number of likely metabolic reactions (#metab)4
    Prediction of binding to human serum albumin (QPlogKhsa)1.458
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)93.989
    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)67.737
    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
    P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
    P04054PLA2G1BPhospholipase A2 group 1BT31479SwissTargetPrediction
    P08473MMENeprilysinT05409SwissTargetPrediction
    Q14416GRM2Metabotropic glutamate receptor 2T62820SwissTargetPrediction
    P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
    Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
    P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
    P08185SERPINA6Corticosteroid binding globulinT88452SwissTargetPrediction
    P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
    P29350PTPN6Protein-tyrosine phosphatase 1CT98264SEA
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction and SEA
    P17706PTPN2T-cell protein-tyrosine phosphataseT49156SwissTargetPrediction and SEA
    Q07869PPARAPeroxisome proliferator-activated receptor alphaT86591SwissTargetPrediction
    P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
    P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
    Q8TDU6GPBAR1G-protein coupled bile acid receptor 1T86273SEA
    P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction and SEA
    P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
    P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
    P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
    Q13133NR1H3LXR-alphaT52297SwissTargetPrediction
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
    P13726F3Coagulation factor VII/tissue factorT72702SEA
    P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
    P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SwissTargetPrediction
    P51449RORCNuclear receptor ROR-gammaT25307SwissTargetPrediction
    Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
    P43116PTGER2Prostanoid EP2 receptorT38529SwissTargetPrediction
    Q9Y5Y4PTGDR2G protein-coupled receptor 44T61722SwissTargetPrediction
    P04035HMGCRHMG-CoA reductaseT53585SwissTargetPrediction
    P11413G6PDGlucose-6-phosphate 1-dehydrogenaseT63484SwissTargetPrediction
    Q16850CYP51A1Cytochrome P450 51 (by homology)T32972SwissTargetPrediction
    Q15722LTB4RLeukotriene B4 receptor 1T59626SwissTargetPrediction
    P20701ITGALIntercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2T35640SwissTargetPrediction
    P11388TOP2ADNA topoisomerase II alphaT17048SwissTargetPrediction
    P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
    P47712PLA2G4ACytosolic phospholipase A2T14834SwissTargetPrediction
    P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
    P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
    P34995PTGER1Prostanoid EP1 receptorT15497SwissTargetPrediction
    P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
    Q9H7Z7PTGES2Prostaglandin E synthase 2T01037SwissTargetPrediction
    Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
    P16885PLCG2Phospholipase C-gamma-2T93922SEA
    Q9Y478PRKAB1AMP-activated protein kinase, beta-1 subunitT38875SwissTargetPrediction
    P49768PSEN1Presenilin 1T93105SwissTargetPrediction
    Q09428ABCC8Sulfonylurea receptor 1T91480SwissTargetPrediction

    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
    T31479DI0230Leishmaniasis[ICD-11: 1F54]P04054PLA2G1B
    T31479DI0335Peroxisomal disease[ICD-11: 5C57]P04054PLA2G1B
    T31479DI0367Rosacea[ICD-11: ED90]P04054PLA2G1B
    T31479DI0398Synthesis disorder[ICD-11: 5C52-5C59]P04054PLA2G1B
    T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
    T62820DI0025Alzheimer disease[ICD-11: 8A20]Q14416GRM2
    T62820DI0051Bipolar disorder[ICD-11: 6A60]Q14416GRM2
    T62820DI0116Dengue fever[ICD-11: 1D2Z]Q14416GRM2
    T62820DI0117Depression[ICD-11: 6A70-6A7Z]Q14416GRM2
    T62820DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]Q14416GRM2
    T62820DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]Q14416GRM2
    T62820DI0308Obesity[ICD-11: 5B80-5B81]Q14416GRM2
    T62820DI0354Psychotic disorder[ICD-11: 6A20-6A25]Q14416GRM2
    T62820DI0370Schizophrenia[ICD-11: 6A20]Q14416GRM2
    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
    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
    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
    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
    T86591DI0187Hyperlipidemia[ICD-11: 5C80]Q07869PPARA
    T86591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q07869PPARA
    T86591DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q07869PPARA
    T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
    T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
    T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
    T86273DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q8TDU6GPBAR1
    T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
    T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
    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
    T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
    T52297DI0117Depression[ICD-11: 6A70-6A7Z]Q13133NR1H3
    T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
    T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
    T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
    T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
    T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
    T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
    T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
    T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
    T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
    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
    T61722DI0102Coronary atherosclerosis[ICD-11: BA52]Q9Y5Y4PTGDR2
    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
    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
    T59626DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]Q15722LTB4R
    T59626DI0355Pulmonary disease[ICD-11: 1B10-1F85]Q15722LTB4R
    T59626DI0361Renal cell carcinoma[ICD-11: 2C90]Q15722LTB4R
    T35640DI0351Psoriasis[ICD-11: EA90]P20701ITGAL
    T35640DI0436Visual system disease[ICD-11: 9E1Z]P20701ITGAL
    T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
    T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
    T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
    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
    T14834DI0039Atopic eczema[ICD-11: EA80]P47712PLA2G4A
    T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
    T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
    T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
    T15497DI0405Thrombosis[ICD-11: DB61-GB90]P34995PTGER1
    T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
    T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
    T38875DI0009Acute diabete complication[ICD-11: 5A2Y]Q9Y478PRKAB1
    T93105DI0320Osteoarthritis[ICD-11: FA00-FA05]P49768PSEN1
    T93105DI0380Shoulder lesion[ICD-11: FB53]P49768PSEN1
    T93105DI0390Soft tissue disorder[ICD-11: FB56]P49768PSEN1
    T91480DI0009Acute diabete complication[ICD-11: 5A2Y]Q09428ABCC8
    T91480DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q09428ABCC8

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