Wharangin



Compound IDCDAMM00385
Common nameWharangin
IUPAC name8-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-[1,3]dioxolo[4,5-h]chromen-6-one
Molecular formulaC17H12O8

Experimental data

Retention time52.46
Adduct[M+H]+
Actual mz345.059
Theoretical mz345.06
Error4.61
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.34

Identifiers and class information

Inchi keyNOZQEJFGIXKUPM-UHFFFAOYSA-N
SmilesO=C1C(OC)=C(OC2=C3OCOC3=CC(O)=C12)C=4C=CC(O)=C(O)C4
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)0
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)4
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)344.277
Computed dipole moment(dipole)4.959
Total solvent accessible surface area (SASA)531.978
Hydrophobic component of SASA (FOSA)152.756
Hydrophilic component of SASA (FISA)182.926
Pie component of the SASA (PISA)196.296
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)929.768
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)6
Free energy of solvation of dipole (dip^2/V)0.0264461
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0159504
Globularity descriptor (glob)0.866006
Predicted polarizability in cubic angstroms (QPpolrz)30.362
Predicted hexadecane/gas partition coefficient (QPlogPC16)10.014
Predicted octanol/gas partition coefficient (QPlogPoct)16.585
Predicted water/gas partition coefficient (QPlogPw)11.536
Predicted octanol/water partition coefficient (QPlogPo/w)1.511
Predicted aqueous solubility (QPlogS)-3.297
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.868
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.636
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)182.479
Predicted brain/blood partition coefficient (QPlogBB)-1.304
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)78.67
Predicted skin permeability, log Kp (QPlogKp)-3.815
PM3 calculated ionization potential (IP(ev))8.871
PM3 calculated electron affinity (EA(eV))0.782
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)-0.135
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)76.261
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)122.295
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
P21397MAOAMonoamine oxidase AT83875SEA
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P16050ALOX15Arachidonate 15-lipoxygenaseT16042SEA
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SEA
O14746TERTTelomerase reverse transcriptaseT86052SEA
P25101EDNRAEndothelin receptor ET-AT23499SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
P24530EDNRBEndothelin receptor ET-BT92828SEA
Q9NPH5NOX4NADPH oxidase 4T29741SwissTargetPrediction and SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SwissTargetPrediction and SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
O60911CTSVCathepsin (V and K)T93653SEA
Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
Q15717ELAVL1ELAV-like protein 1T78349SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA
H3BPQ1TCF4Transcription factor 7-like 2T54646SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
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
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
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
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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