(S)-4\',7-Dihydroxy-3\',8-diprenylflavanone



Compound IDCDAMM01871
Common name(S)-4\',7-Dihydroxy-3\',8-diprenylflavanone
IUPAC name7-hydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Molecular formulaC25H28O4

Experimental data

Retention time28.21
Adduct[M+H]+
Actual mz393.204
Theoretical mz393.206
Error5.28
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.627

Identifiers and class information

Inchi keyCUFAXDWQDQQKFF-UHFFFAOYNA-N
SmilesO=C1C2=CC=C(O)C(=C2OC(C3=CC=C(O)C(=C3)CC=C(C)C)C1)CC=C(C)C
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Curcuma longa 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)6
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)392.494
    Computed dipole moment(dipole)2.785
    Total solvent accessible surface area (SASA)710.774
    Hydrophobic component of SASA (FOSA)416.501
    Hydrophilic component of SASA (FISA)122.434
    Pie component of the SASA (PISA)171.839
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1305.24
    Number of hydrogen bond donors (donorHB)2
    Number of hydrogen bond acceptors (accptHB)4.25
    Free energy of solvation of dipole (dip^2/V)0.0059445
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0084561
    Globularity descriptor (glob)0.812632
    Predicted polarizability in cubic angstroms (QPpolrz)43.87
    Predicted hexadecane/gas partition coefficient (QPlogPC16)12.886
    Predicted octanol/gas partition coefficient (QPlogPoct)19.605
    Predicted water/gas partition coefficient (QPlogPw)9.223
    Predicted octanol/water partition coefficient (QPlogPo/w)4.87
    Predicted aqueous solubility (QPlogS)-6.526
    Conformation-independent predicted aqueous solubility (CIQPlogS)-6.23
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.383
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)683.69
    Predicted brain/blood partition coefficient (QPlogBB)-1.034
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)327.984
    Predicted skin permeability, log Kp (QPlogKp)-2.595
    PM3 calculated ionization potential (IP(ev))9.155
    PM3 calculated electron affinity (EA(eV))0.392
    Number of likely metabolic reactions (#metab)10
    Prediction of binding to human serum albumin (QPlogKhsa)1.013
    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)73.379
    Number of nitrogen and oxygen atoms (#NandO)4
    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
    P04054PLA2G1BPhospholipase A2 group 1BT31479SwissTargetPrediction
    P27338MAOBMonoamine oxidase BT83011SEA
    P23141CES1Acyl coenzyme A:cholesterol acyltransferaseT76369SwissTargetPrediction
    P11926ODC1Ornithine decarboxylaseT60366SEA
    Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
    P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction and SEA
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
    P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
    P14061HSD17B1Estradiol 17-beta-dehydrogenase 1T44011SwissTargetPrediction
    P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
    P07711CTSLCathepsin LT98691SwissTargetPrediction
    P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SwissTargetPrediction
    P20151KLK2Kallikrein 2T01908SEA
    P19793RXRARetinoid X receptor alpha (by homology)T13726SwissTargetPrediction
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
    P14679TYRTyrosinaseT97035SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    O60911CTSVCathepsin (V and K)T93653SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA

    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
    T31479DI0230Leishmaniasis[ICD-11: 1F54]P04054PLA2G1B
    T31479DI0335Peroxisomal disease[ICD-11: 5C57]P04054PLA2G1B
    T31479DI0367Rosacea[ICD-11: ED90]P04054PLA2G1B
    T31479DI0398Synthesis disorder[ICD-11: 5C52-5C59]P04054PLA2G1B
    T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
    T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
    T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
    T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
    T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
    T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
    T76369DI0335Peroxisomal disease[ICD-11: 5C57]P23141CES1
    T76369DI0398Synthesis disorder[ICD-11: 5C52-5C59]P23141CES1
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    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
    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
    T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
    T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
    T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
    T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
    T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
    T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
    T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
    T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
    T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
    T13726DI0225Kaposi sarcoma[ICD-11: 2B57]P19793RXRA
    T13726DI0283Mycosis fungoides[ICD-11: 2B01]P19793RXRA
    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
    T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
    T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1

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