Diospyrin



Compound IDCDAMM02773
Common nameDiospyrin
IUPAC name3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-4,5,7-triol
Molecular formulaC21H24O13

Experimental data

Retention time12.54
Adduct[M+H]+
Actual mz485.125
Theoretical mz485.129
Error8.81
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.7037

Identifiers and class information

Inchi keyXCZZWPJIGBONJX-UHFFFAOYNA-N
SmilesOC=1C=C(O)C2=C(OC(C3=CC(O)=C(O)C(O)=C3)C(OC4OC(CO)C(O)C(O)C4O)C2O)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)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)484.413
Computed dipole moment(dipole)6.989
Total solvent accessible surface area (SASA)659.206
Hydrophobic component of SASA (FOSA)136.322
Hydrophilic component of SASA (FISA)392.724
Pie component of the SASA (PISA)130.16
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1249.83
Number of hydrogen bond donors (donorHB)10
Number of hydrogen bond acceptors (accptHB)16.4
Free energy of solvation of dipole (dip^2/V)0.0390833
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0786725
Globularity descriptor (glob)0.851227
Predicted polarizability in cubic angstroms (QPpolrz)36.76
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.779
Predicted octanol/gas partition coefficient (QPlogPoct)36.937
Predicted water/gas partition coefficient (QPlogPw)32.794
Predicted octanol/water partition coefficient (QPlogPo/w)-2.613
Predicted aqueous solubility (QPlogS)-1.854
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.12
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.56
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1.869
Predicted brain/blood partition coefficient (QPlogBB)-3.833
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.556
Predicted skin permeability, log Kp (QPlogKp)-7.051
PM3 calculated ionization potential (IP(ev))8.604
PM3 calculated electron affinity (EA(eV))-0.237
Number of likely metabolic reactions (#metab)11
Prediction of binding to human serum albumin (QPlogKhsa)-1.128
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)233.054
Number of nitrogen and oxygen atoms (#NandO)13
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
Q12809KCNH2HERGT20251SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction and SEA
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P14867GABRA1GABA-A receptor; alpha-1/beta-2/gamma-2T51487SwissTargetPrediction
Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
P11387TOP1DNA topoisomerase IT09826SEA
P08581METHepatocyte growth factor receptorT40474SwissTargetPrediction
Q13627DYRK1ADual-specificity tyrosine-phosphorylation regulated kinase 1AT92803SwissTargetPrediction
P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
P49763PGFPlacenta growth factorT70792SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
P10415BCL2Apoptosis regulator Bcl-2T31309SwissTargetPrediction
P52209PGD6-phosphogluconate dehydrogenaseT76497SwissTargetPrediction and SEA
P22083FUT4Fucosyltransferase 4T51146SwissTargetPrediction
P42224STAT1Signal transducer and activator of transcription 1-alpha/betaT64205SwissTargetPrediction
P10636MAPTMicrotubule-associated protein tauT45593SwissTargetPrediction
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T51487DI0014Acute respiratory distress syndrome[ICD-11: CB00]P14867GABRA1
T51487DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P14867GABRA1
T51487DI0082Chronic insomnia[ICD-11: 7A00]P14867GABRA1
T51487DI0087Chronic pain[ICD-11: MG30]P14867GABRA1
T51487DI0101Corneal disease[ICD-11: 9A76-9A78]P14867GABRA1
T51487DI0112Cystitis[ICD-11: GC00]P14867GABRA1
T51487DI0117Depression[ICD-11: 6A70-6A7Z]P14867GABRA1
T51487DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P14867GABRA1
T51487DI0173Headache[ICD-11: 8A80-8A84]P14867GABRA1
T51487DI0214Insomnia[ICD-11: 7A00-7A0Z]P14867GABRA1
T51487DI0243Malaria[ICD-11: 1F40-1F45]P14867GABRA1
T51487DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P14867GABRA1
T51487DI0411Tonus and reflex abnormality[ICD-11: MB47]P14867GABRA1
T60529DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]Q5T7T8COX1
T60529DI0145Female pelvic pain[ICD-11: GA34]Q5T7T8COX1
T60529DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q5T7T8COX1
T60529DI0207Indeterminate colitis[ICD-11: DD72]Q5T7T8COX1
T60529DI0306Nutritional deficiency[ICD-11: 5B50-5B71]Q5T7T8COX1
T60529DI0320Osteoarthritis[ICD-11: FA00-FA05]Q5T7T8COX1
T60529DI0324Pain[ICD-11: MG30-MG3Z]Q5T7T8COX1
T60529DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q5T7T8COX1
T60529DI0366Rheumatoid arthritis[ICD-11: FA20]Q5T7T8COX1
T60529DI0372Seborrhoeic dermatitis[ICD-11: EA81]Q5T7T8COX1
T60529DI0416Tuberculosis[ICD-11: 1B10-1B12]Q5T7T8COX1
T60529DI0419Ulcerative colitis[ICD-11: DD71]Q5T7T8COX1
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
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
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
T92803DI0113Cytomegaloviral disease[ICD-11: 1D82]Q13627DYRK1A
T88304DI0012Acute myeloid leukaemia[ICD-11: 2A60]P26358DNMT1
T88304DI0284Myelodysplastic syndrome[ICD-11: 2A37]P26358DNMT1
T88304DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P26358DNMT1
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
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
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
T31309DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10415BCL2
T31309DI0249Mature B-cell leukaemia[ICD-11: 2A82]P10415BCL2
T31309DI0273Motor neuron disease[ICD-11: 8B60]P10415BCL2
T31309DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P10415BCL2
T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
T51146DI0441Appendicitis[ICD-11: DB10]P22083FUT4
T64205DI0383Skin and skin-structure infection[ICD-11: 1F28-1G0Z]P42224STAT1
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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