Guangsangon L



Compound IDCDAMM00618
Common nameGuangsangon L
IUPAC name5-[6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxybenzaldehyde
Molecular formulaC27H24O8

Experimental data

Retention time12.75
Adduct[M+Na]+
Actual mz499.139
Theoretical mz499.136
Error4.97
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.8754

Identifiers and class information

Inchi keyQCPFZAFDSWGNMR-ZKKCRHENNA-N
SmilesO=CC=1C=C(C(O)=CC1O)C2C=C(C)CC(C3=CC=C(O)C=C3O)C2C(=O)C4=CC=C(O)C=C4O
SuperclassPhenylpropanoids and polyketides
ClassDiarylheptanoids

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)2
    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)9
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)476.482
    Computed dipole moment(dipole)8.101
    Total solvent accessible surface area (SASA)691.929
    Hydrophobic component of SASA (FOSA)125.83
    Hydrophilic component of SASA (FISA)329.934
    Pie component of the SASA (PISA)236.164
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1337.55
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)6.5
    Free energy of solvation of dipole (dip^2/V)0.0490662
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0187881
    Globularity descriptor (glob)0.848483
    Predicted polarizability in cubic angstroms (QPpolrz)43.851
    Predicted hexadecane/gas partition coefficient (QPlogPC16)15.497
    Predicted octanol/gas partition coefficient (QPlogPoct)25.509
    Predicted water/gas partition coefficient (QPlogPw)15.511
    Predicted octanol/water partition coefficient (QPlogPo/w)2.483
    Predicted aqueous solubility (QPlogS)-4.732
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.201
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.11
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)7.364
    Predicted brain/blood partition coefficient (QPlogBB)-3.034
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.449
    Predicted skin permeability, log Kp (QPlogKp)-5.904
    PM3 calculated ionization potential (IP(ev))8.916
    PM3 calculated electron affinity (EA(eV))0.501
    Number of likely metabolic reactions (#metab)11
    Prediction of binding to human serum albumin (QPlogKhsa)0.456
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)44.043
    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)181.649
    Number of nitrogen and oxygen atoms (#NandO)8
    Number of violations of Lipinski’s rule of five (RuleOfFive)1
    Number of violations of Jorgensen’s rule of three (RuleOfThree)2

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SwissTargetPrediction
    P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
    Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
    P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
    P51681CCR5C-C chemokine receptor type 5T09960SwissTargetPrediction
    O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
    Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
    Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
    P49327FASNFatty acid synthaseT16514SwissTargetPrediction
    O75874IDH1Isocitrate dehydrogenase [NADP] cytoplasmicT69563SwissTargetPrediction
    P16050ALOX15Arachidonate 15-lipoxygenaseT16042SwissTargetPrediction
    P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction
    P07711CTSLCathepsin LT98691SwissTargetPrediction
    P24723PRKCHProtein kinase C etaT40149SwissTargetPrediction
    P35222CTNNB1Axin1/beta-cateninT82795SwissTargetPrediction
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P05771PRKCBProtein kinase C betaT40276SwissTargetPrediction
    Q02156PRKCEProtein kinase C epsilonT00895SwissTargetPrediction
    P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SwissTargetPrediction
    P06870KLK1Kallikrein 1T40000SwissTargetPrediction
    P20151KLK2Kallikrein 2T01908SwissTargetPrediction
    Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
    P05129PRKCGProtein kinase C gammaT47107SwissTargetPrediction
    P63316TNNC1Troponin, cardiac muscleT12966SwissTargetPrediction
    P14625HSP90B1EndoplasminT81311SwissTargetPrediction

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
    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
    T09960DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P51681CCR5
    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
    T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
    T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
    T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
    T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
    T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
    T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
    T16514DI0096concerning food/fluid intake symptom[ICD-11: MG43]P49327FASN
    T69563DI0012Acute myeloid leukaemia[ICD-11: 2A60]O75874IDH1
    T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
    T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
    T40149DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P24723PRKCH
    T82795DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35222CTNNB1
    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
    T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
    T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
    T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
    T47107DI0012Acute myeloid leukaemia[ICD-11: 2A60]P05129PRKCG
    T47107DI0248Mastocytosis[ICD-11: 2A21]P05129PRKCG
    T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
    T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
    T81311DI0238Lung cancer[ICD-11: 2C25]P14625HSP90B1

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