Dulciol A



Compound IDCDAMM03000
Common nameDulciol A
IUPAC name4-(3,7-dimethylocta-2,6-dienyl)-2,3,6,8-tetrahydroxy-1-(3-methylbut-2-enyl)xanthen-9-one
Molecular formulaC28H32O6

Experimental data

Retention time1.24
Adduct[M+H]+
Actual mz465.231
Theoretical mz465.227
Error7.79
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5982

Identifiers and class information

Inchi keyGPHYDWLQZOOUFR-LICLKQGHSA-N
SmilesO=C1C=2C(O)=CC(O)=CC2OC3=C1C(=C(O)C(O)=C3CC=C(C)CCC=C(C)C)CC=C(C)C
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

Plant source

  • Clitoria ternatea 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)0
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)11
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)464.557
    Computed dipole moment(dipole)4.1
    Total solvent accessible surface area (SASA)643.223
    Hydrophobic component of SASA (FOSA)372.424
    Hydrophilic component of SASA (FISA)168.622
    Pie component of the SASA (PISA)102.177
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1339.7
    Number of hydrogen bond donors (donorHB)3
    Number of hydrogen bond acceptors (accptHB)4.5
    Free energy of solvation of dipole (dip^2/V)0.0125481
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0121175
    Globularity descriptor (glob)0.913711
    Predicted polarizability in cubic angstroms (QPpolrz)41.374
    Predicted hexadecane/gas partition coefficient (QPlogPC16)13.26
    Predicted octanol/gas partition coefficient (QPlogPoct)20.769
    Predicted water/gas partition coefficient (QPlogPw)9.509
    Predicted octanol/water partition coefficient (QPlogPo/w)4.434
    Predicted aqueous solubility (QPlogS)-4.266
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.484
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.416
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)249.38
    Predicted brain/blood partition coefficient (QPlogBB)-1.446
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)110.263
    Predicted skin permeability, log Kp (QPlogKp)-3.211
    PM3 calculated ionization potential (IP(ev))8.973
    PM3 calculated electron affinity (EA(eV))0.585
    Number of likely metabolic reactions (#metab)13
    Prediction of binding to human serum albumin (QPlogKhsa)0.807
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)95.808
    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)108.625
    Number of nitrogen and oxygen atoms (#NandO)6
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    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
    P21397MAOAMonoamine oxidase AT83875SEA
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SwissTargetPrediction and SEA
    P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    O60341KDM1ALysine-specific histone demethylase 1T16739SwissTargetPrediction
    Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
    P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
    P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
    Q9HC97GPR35G-protein coupled receptor 35T56143SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
    P49327FASNFatty acid synthaseT16514SwissTargetPrediction
    O75874IDH1Isocitrate dehydrogenase [NADP] cytoplasmicT69563SwissTargetPrediction
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SwissTargetPrediction
    P16050ALOX15Arachidonate 15-lipoxygenaseT16042SwissTargetPrediction
    P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction
    P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
    P24723PRKCHProtein kinase C etaT40149SwissTargetPrediction
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P05771PRKCBProtein kinase C betaT40276SwissTargetPrediction
    Q02156PRKCEProtein kinase C epsilonT00895SwissTargetPrediction
    P47871GCGRGlucagon receptorT60182SwissTargetPrediction
    Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
    P25024CXCR1Interleukin-8 receptor AT00884SwissTargetPrediction
    P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
    P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    Q9NPH5NOX4NADPH oxidase 4T29741SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    Q04760GLO1Glyoxalase IT88285SEA
    P05129PRKCGProtein kinase C gammaT47107SwissTargetPrediction
    P14625HSP90B1EndoplasminT81311SwissTargetPrediction
    O60911CTSVCathepsin (V and K)T93653SEA
    Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    O95749GGPS1GeranyltranstransferaseT86528SEA
    Q15717ELAVL1ELAV-like protein 1T78349SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
    T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T16739DI0012Acute myeloid leukaemia[ICD-11: 2A60]O60341KDM1A
    T16739DI0025Alzheimer disease[ICD-11: 8A20]O60341KDM1A
    T16739DI0138Ewing sarcoma[ICD-11: 2B52]O60341KDM1A
    T16739DI0238Lung cancer[ICD-11: 2C25]O60341KDM1A
    T16739DI0241Lymphoma[ICD-11: 2A80-2A86]O60341KDM1A
    T16739DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]O60341KDM1A
    T16739DI0284Myelodysplastic syndrome[ICD-11: 2A37]O60341KDM1A
    T16739DI0286Myeloproliferative neoplasm[ICD-11: 2A20]O60341KDM1A
    T16739DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O60341KDM1A
    T60529DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]Q5T7T8COX1
    T60529DI0145Female pelvic pain[ICD-11: GA34]Q5T7T8COX1
    T60529DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q5T7T8COX1
    T60529DI0207Indeterminate colitis[ICD-11: DD72]Q5T7T8COX1
    T60529DI0306Nutritional deficiency[ICD-11: 5B50-5B71]Q5T7T8COX1
    T60529DI0320Osteoarthritis[ICD-11: FA00-FA05]Q5T7T8COX1
    T60529DI0324Pain[ICD-11: MG30-MG3Z]Q5T7T8COX1
    T60529DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q5T7T8COX1
    T60529DI0366Rheumatoid arthritis[ICD-11: FA20]Q5T7T8COX1
    T60529DI0372Seborrhoeic dermatitis[ICD-11: EA81]Q5T7T8COX1
    T60529DI0416Tuberculosis[ICD-11: 1B10-1B12]Q5T7T8COX1
    T60529DI0419Ulcerative colitis[ICD-11: DD71]Q5T7T8COX1
    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
    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
    T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
    T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
    T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
    T16514DI0096concerning food/fluid intake symptom[ICD-11: MG43]P49327FASN
    T69563DI0012Acute myeloid leukaemia[ICD-11: 2A60]O75874IDH1
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T84631DI0053Blood-forming organ disease[ICD-11: 3C0Z]P00742F10
    T84631DI0080Christmas disease[ICD-11: 3B11]P00742F10
    T84631DI0091Coagulation defect[ICD-11: 3B10]P00742F10
    T84631DI0103Coronary thrombosis[ICD-11: BA43]P00742F10
    T84631DI0114Deep vein thrombosis[ICD-11: BD71]P00742F10
    T84631DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P00742F10
    T84631DI0405Thrombosis[ICD-11: DB61-GB90]P00742F10
    T84631DI0433Venous thromboembolism[ICD-11: BD72]P00742F10
    T40149DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P24723PRKCH
    T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
    T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
    T40276DI0123Diffuse large B-cell lymphoma[ICD-11: 2A81]P05771PRKCB
    T40276DI0241Lymphoma[ICD-11: 2A80-2A86]P05771PRKCB
    T40276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P05771PRKCB
    T00895DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]Q02156PRKCE
    T00895DI0243Malaria[ICD-11: 1F40-1F45]Q02156PRKCE
    T60182DI0193Hypo-glycaemia[ICD-11: 5A41]P47871GCGR
    T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
    T00884DI0324Pain[ICD-11: MG30-MG3Z]P25024CXCR1
    T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
    T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
    T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
    T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
    T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
    T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
    T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
    T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
    T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
    T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
    T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
    T47107DI0012Acute myeloid leukaemia[ICD-11: 2A60]P05129PRKCG
    T47107DI0248Mastocytosis[ICD-11: 2A21]P05129PRKCG
    T81311DI0238Lung cancer[ICD-11: 2C25]P14625HSP90B1
    T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
    T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
    T86528DI0057Bone paget disease[ICD-11: FB85]O95749GGPS1
    T86528DI0237Low bone mass disorder[ICD-11: FB83]O95749GGPS1
    T86528DI0267Mineral excesses[ICD-11: 5B91]O95749GGPS1
    T86528DI0281Musculoskeletal disorder[ICD-11: FA00-FC0Z]O95749GGPS1
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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