Dihydrocycloartomunin



Compound IDCDAMM00607
Common nameDihydrocycloartomunin
IUPAC name2,3,8-trihydroxy-10-methoxy-11-(3-methylbut-2-enyl)-6-(2-methylprop-1-enyl)-6H-chromeno[4,3-b]chromen-7-one
Molecular formulaC26H26O7

Experimental data

Retention time13.05
Adduct[M+Na]+
Actual mz473.161
Theoretical mz473.157
Error7.78
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.2878

Identifiers and class information

Inchi keyFIYIGIGIGDUJQB-UHFFFAOYNA-N
SmilesO=C1C2=C(O)C=C(OC)C(=C2OC=3C=4C=C(O)C(O)=CC4OC(C=C(C)C)C13)CC=C(C)C
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

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)7
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)450.487
    Computed dipole moment(dipole)2.167
    Total solvent accessible surface area (SASA)773.312
    Hydrophobic component of SASA (FOSA)425.975
    Hydrophilic component of SASA (FISA)153.002
    Pie component of the SASA (PISA)194.335
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1418.25
    Number of hydrogen bond donors (donorHB)2
    Number of hydrogen bond acceptors (accptHB)5.25
    Free energy of solvation of dipole (dip^2/V)0.0033107
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0096011
    Globularity descriptor (glob)0.789428
    Predicted polarizability in cubic angstroms (QPpolrz)47.966
    Predicted hexadecane/gas partition coefficient (QPlogPC16)14.383
    Predicted octanol/gas partition coefficient (QPlogPoct)21.63
    Predicted water/gas partition coefficient (QPlogPw)10.499
    Predicted octanol/water partition coefficient (QPlogPo/w)4.986
    Predicted aqueous solubility (QPlogS)-7.139
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.211
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.866
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)350.736
    Predicted brain/blood partition coefficient (QPlogBB)-1.495
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)159.414
    Predicted skin permeability, log Kp (QPlogKp)-2.983
    PM3 calculated ionization potential (IP(ev))8.679
    PM3 calculated electron affinity (EA(eV))0.788
    Number of likely metabolic reactions (#metab)10
    Prediction of binding to human serum albumin (QPlogKhsa)1.08
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
    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)110.29
    Number of nitrogen and oxygen atoms (#NandO)7
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    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
    P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SwissTargetPrediction and SEA
    P04054PLA2G1BPhospholipase A2 group 1BT31479SwissTargetPrediction
    P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
    O60341KDM1ALysine-specific histone demethylase 1T16739SwissTargetPrediction
    P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
    Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
    P10828THRBThyroid hormone receptor beta-1T98933SwissTargetPrediction
    Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
    P14061HSD17B1Estradiol 17-beta-dehydrogenase 1T44011SwissTargetPrediction
    P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
    P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
    P49327FASNFatty acid synthaseT16514SwissTargetPrediction
    O75874IDH1Isocitrate dehydrogenase [NADP] cytoplasmicT69563SwissTargetPrediction
    P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
    P24723PRKCHProtein kinase C etaT40149SwissTargetPrediction
    P08238HSP90AB1Heat shock protein HSP 90-betaT96623SwissTargetPrediction
    P35222CTNNB1Axin1/beta-cateninT82795SwissTargetPrediction
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P41743PRKCIProtein kinase C iotaT83174SwissTargetPrediction
    P01375TNFTNF-alphaT20178SwissTargetPrediction
    P05771PRKCBProtein kinase C betaT40276SwissTargetPrediction
    Q02156PRKCEProtein kinase C epsilonT00895SwissTargetPrediction
    P47871GCGRGlucagon receptorT60182SwissTargetPrediction
    P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
    Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
    P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
    O14980XPO1Exportin-1T51407SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
    P14679TYRTyrosinaseT97035SEA
    Q14680MELKMaternal embryonic leucine zipper kinaseT96892SwissTargetPrediction
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P05129PRKCGProtein kinase C gammaT47107SwissTargetPrediction
    P63316TNNC1Troponin, cardiac muscleT12966SwissTargetPrediction
    P14625HSP90B1EndoplasminT81311SwissTargetPrediction
    O60911CTSVCathepsin (V and K)T93653SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
    T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
    T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
    T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
    T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
    T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
    T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
    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
    T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
    T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    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
    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
    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
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    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
    T98933DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10828THRB
    T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
    T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
    T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
    T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
    T16514DI0096concerning food/fluid intake symptom[ICD-11: MG43]P49327FASN
    T69563DI0012Acute myeloid leukaemia[ICD-11: 2A60]O75874IDH1
    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
    T96623DI0062Breast cancer[ICD-11: 2C60-2C6Y]P08238HSP90AB1
    T96623DI0238Lung cancer[ICD-11: 2C25]P08238HSP90AB1
    T96623DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P08238HSP90AB1
    T96623DI0249Mature B-cell leukaemia[ICD-11: 2A82]P08238HSP90AB1
    T96623DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P08238HSP90AB1
    T96623DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P08238HSP90AB1
    T96623DI0395Stomach cancer[ICD-11: 2B72]P08238HSP90AB1
    T82795DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35222CTNNB1
    T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
    T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
    T83174DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P41743PRKCI
    T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
    T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
    T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
    T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
    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
    T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
    T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
    T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
    T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
    T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
    T51407DI0234Liposarcoma[ICD-11: 2B59]O14980XPO1
    T51407DI0274Multiple myeloma[ICD-11: 2A83]O14980XPO1
    T51407DI0395Stomach cancer[ICD-11: 2B72]O14980XPO1
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T96892DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q14680MELK
    T96892DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q14680MELK
    T96892DI0249Mature B-cell leukaemia[ICD-11: 2A82]Q14680MELK
    T96892DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q14680MELK
    T96892DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q14680MELK
    T96892DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q14680MELK
    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
    T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
    T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV

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