Biochanin A 7-(6-malonylglucoside)



Compound IDCDAMM02843
Common nameBiochanin A 7-(6-malonylglucoside)
IUPAC name3-oxo-3-[[3,4,5-trihydroxy-6-[5-hydroxy-3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid
Molecular formulaC25H24O13

Experimental data

Retention time13.15
Adduct[M+H]+
Actual mz533.133
Theoretical mz533.129
Error7.92
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.445

Identifiers and class information

Inchi keyVRCBYTZZZFFKEN-UHFFFAOYNA-N
SmilesO=C(O)CC(=O)OCC1OC(OC2=CC(O)=C3C(=O)C(=COC3=C2)C=4C=CC(OC)=CC4)C(O)C(O)C1O
SuperclassPhenylpropanoids and polyketides
ClassIsoflavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)2
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)1
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)12
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)532.457
Computed dipole moment(dipole)8.02
Total solvent accessible surface area (SASA)751.433
Hydrophobic component of SASA (FOSA)247.919
Hydrophilic component of SASA (FISA)292.196
Pie component of the SASA (PISA)211.318
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1426.01
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)13.55
Free energy of solvation of dipole (dip^2/V)0.0451089
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0312327
Globularity descriptor (glob)0.815374
Predicted polarizability in cubic angstroms (QPpolrz)45.228
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.676
Predicted octanol/gas partition coefficient (QPlogPoct)27.856
Predicted water/gas partition coefficient (QPlogPw)20.046
Predicted octanol/water partition coefficient (QPlogPo/w)1.226
Predicted aqueous solubility (QPlogS)-3.326
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.554
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.72
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4.252
Predicted brain/blood partition coefficient (QPlogBB)-3.09
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.72
Predicted skin permeability, log Kp (QPlogKp)-5.008
PM3 calculated ionization potential (IP(ev))8.514
PM3 calculated electron affinity (EA(eV))0.291
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.737
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)19.459
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)221.906
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)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
O95718ESRRBEstrogen-related receptor betaT42025SEA
P01375TNFTNF-alphaT20178SwissTargetPrediction
P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SwissTargetPrediction and SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P14679TYRTyrosinaseT97035SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P49862KLK7Kallikrein-7T79155SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
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
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
T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
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
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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