4\',5-Dihydroxy-7-methoxyisoflavone 3\'-O-(3\'\'-E-cinnamoylglucoside)



Compound IDCDAMM01947
Common name4\',5-Dihydroxy-7-methoxyisoflavone 3\'-O-(3\'\'-E-cinnamoylglucoside)
IUPAC name[3,5-dihydroxy-2-[2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxochromen-3-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl] 3-phenylprop-2-enoate
Molecular formulaC31H28O12

Experimental data

Retention time18.78
Adduct[M+K]+
Actual mz631.12
Theoretical mz631.121
Error1.68
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7957

Identifiers and class information

Inchi keyNZDCPGVUPNQJKH-RSXKQKNMNA-N
SmilesO=C(OC1C(O)C(OC=2C=C(C=CC2O)C3=COC4=CC(OC)=CC(O)=C4C3=O)OC(CO)C1O)C=CC=5C=CC=CC5
SuperclassPhenylpropanoids and polyketides
ClassIsoflavonoids

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)0
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)14
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)592.555
    Computed dipole moment(dipole)10.603
    Total solvent accessible surface area (SASA)874.958
    Hydrophobic component of SASA (FOSA)207.713
    Hydrophilic component of SASA (FISA)239.591
    Pie component of the SASA (PISA)427.653
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1658.64
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)13.3
    Free energy of solvation of dipole (dip^2/V)0.0677842
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0304015
    Globularity descriptor (glob)0.774484
    Predicted polarizability in cubic angstroms (QPpolrz)55.319
    Predicted hexadecane/gas partition coefficient (QPlogPC16)19.375
    Predicted octanol/gas partition coefficient (QPlogPoct)32.93
    Predicted water/gas partition coefficient (QPlogPw)22.234
    Predicted octanol/water partition coefficient (QPlogPo/w)2.631
    Predicted aqueous solubility (QPlogS)-4.987
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.119
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.221
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)52.949
    Predicted brain/blood partition coefficient (QPlogBB)-2.943
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)20.653
    Predicted skin permeability, log Kp (QPlogKp)-3.085
    PM3 calculated ionization potential (IP(ev))8.739
    PM3 calculated electron affinity (EA(eV))0.774
    Number of likely metabolic reactions (#metab)6
    Prediction of binding to human serum albumin (QPlogKhsa)-0.14
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)47.285
    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)189.847
    Number of nitrogen and oxygen atoms (#NandO)12
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    Number of violations of Jorgensen’s rule of three (RuleOfThree)0

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    O43570CA12Carbonic anhydrase XIIT16987SEA
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SEA
    P60568IL2Interleukin-2T61698SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    P17931LGALS3Galectin-3T72038SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P10636MAPTMicrotubule-associated protein tauT45593SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    P09382LGALS1Galectin-1T09544SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P05231IL6Interleukin-6T32578SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
    T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
    T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
    T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
    T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
    T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
    T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
    T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
    T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
    T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
    T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
    T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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