Isoorientin 2\'\'-p-hydroxybenzoate



Compound IDCDAMM01919
Common nameIsoorientin 2\'\'-p-hydroxybenzoate
IUPAC name[2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 4-hydroxybenzoate
Molecular formulaC28H24O13

Experimental data

Retention time28.25
Adduct[M+H]+
Actual mz569.124
Theoretical mz569.129
Error8.74
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.1273

Identifiers and class information

Inchi keyCMHUXCFQCMZVCA-BBBGOSSINA-N
SmilesO=C(OC1C(O)C(O)C(OC1C2=C(O)C=C3OC(=CC(=O)C3=C2O)C=4C=CC(O)=C(O)C4)CO)C5=CC=C(O)C=C5
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Curcuma longa L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)7
    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)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)568.49
    Computed dipole moment(dipole)8.474
    Total solvent accessible surface area (SASA)809.605
    Hydrophobic component of SASA (FOSA)102.074
    Hydrophilic component of SASA (FISA)362.528
    Pie component of the SASA (PISA)345.004
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1525.89
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)14.05
    Free energy of solvation of dipole (dip^2/V)0.0470563
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0459147
    Globularity descriptor (glob)0.791724
    Predicted polarizability in cubic angstroms (QPpolrz)51.144
    Predicted hexadecane/gas partition coefficient (QPlogPC16)19.026
    Predicted octanol/gas partition coefficient (QPlogPoct)36.566
    Predicted water/gas partition coefficient (QPlogPw)28.145
    Predicted octanol/water partition coefficient (QPlogPo/w)0.24
    Predicted aqueous solubility (QPlogS)-4.19
    Conformation-independent predicted aqueous solubility (CIQPlogS)-6.145
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.547
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)3.614
    Predicted brain/blood partition coefficient (QPlogBB)-3.955
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.135
    Predicted skin permeability, log Kp (QPlogKp)-5.929
    PM3 calculated ionization potential (IP(ev))9.223
    PM3 calculated electron affinity (EA(eV))1.097
    Number of likely metabolic reactions (#metab)10
    Prediction of binding to human serum albumin (QPlogKhsa)-0.48
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
    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)230.121
    Number of nitrogen and oxygen atoms (#NandO)13
    Number of violations of Lipinski’s rule of five (RuleOfFive)3
    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
    P02766TTRTransthyretinT86462SEA
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    P15121AKR1B1Aldose reductaseT26623SEA
    P05164MPOMyeloperoxidaseT23471SEA
    P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    O95271TNKSTankyrase-1T83059SEA
    P18054ALOX12Arachidonate 12-lipoxygenaseT35527SEA
    O14746TERTTelomerase reverse transcriptaseT86052SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P52789HK2Hexokinase type IIT96685SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SEA
    P60568IL2Interleukin-2T61698SEA
    P49763PGFPlacenta growth factorT70792SEA
    P17931LGALS3Galectin-3T72038SEA
    P14679TYRTyrosinaseT97035SEA
    Q9NPH5NOX4NADPH oxidase 4T29741SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    P52209PGD6-phosphogluconate dehydrogenaseT76497SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    Q04760GLO1Glyoxalase IT88285SEA
    Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    P09382LGALS1Galectin-1T09544SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P05231IL6Interleukin-6T32578SEA
    Q99417MYCBPMYCBP messenger RNAT37298SEA
    P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
    Q15717ELAVL1ELAV-like protein 1T78349SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
    T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
    T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
    T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
    T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T83059DI0060Brain cancer[ICD-11: 2A00]O95271TNKS
    T83059DI0062Breast cancer[ICD-11: 2C60-2C6Y]O95271TNKS
    T83059DI0321Ovarian cancer[ICD-11: 2C73]O95271TNKS
    T83059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O95271TNKS
    T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
    T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
    T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
    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
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
    T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
    T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
    T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
    T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
    T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
    T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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