Naringin



Compound IDCDAMM01374
Common nameNaringin
IUPAC name7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Molecular formulaC27H32O14

Experimental data

Retention time19.55
Adduct[M+K]+
Actual mz619.145
Theoretical mz619.142
Error3.94
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.7713

Identifiers and class information

Inchi keyDFPMSGMNTNDNHN-ZPHOTFPESA-N
SmilesO=C1C2=C(O)C=C(OC3OC(CO)C(O)C(O)C3OC4OC(C)C(O)C(O)C4O)C=C2OC(C5=CC=C(O)C=C5)C1
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

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)13
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)580.541
Computed dipole moment(dipole)5.205
Total solvent accessible surface area (SASA)840.03
Hydrophobic component of SASA (FOSA)282.16
Hydrophilic component of SASA (FISA)355.148
Pie component of the SASA (PISA)202.721
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1593.79
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)19.3
Free energy of solvation of dipole (dip^2/V)0.0169955
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0607871
Globularity descriptor (glob)0.785522
Predicted polarizability in cubic angstroms (QPpolrz)51.218
Predicted hexadecane/gas partition coefficient (QPlogPC16)18.619
Predicted octanol/gas partition coefficient (QPlogPoct)38.675
Predicted water/gas partition coefficient (QPlogPw)31.93
Predicted octanol/water partition coefficient (QPlogPo/w)-1.329
Predicted aqueous solubility (QPlogS)-3.179
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.067
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.969
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4.246
Predicted brain/blood partition coefficient (QPlogBB)-4.057
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.351
Predicted skin permeability, log Kp (QPlogKp)-6.103
PM3 calculated ionization potential (IP(ev))9.123
PM3 calculated electron affinity (EA(eV))0.219
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-1.127
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)232.716
Number of nitrogen and oxygen atoms (#NandO)14
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
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction and SEA
P11387TOP1DNA topoisomerase IT09826SEA
P20151KLK2Kallikrein 2T01908SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
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
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
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
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
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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