Isogemichalcone C



Compound IDCDAMM00763
Common nameIsogemichalcone C
IUPAC name[4-[3-[3-(2,4-dihydroxyphenyl)prop-2-enoyl]-2,6-dihydroxyphenyl]-2-methylbut-2-enyl] 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Molecular formulaC30H28O9

Experimental data

Retention time13.06
Adduct[M+H]+
Actual mz533.183
Theoretical mz533.18
Error4.92
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.3722

Identifiers and class information

Inchi keyOFKHJNZDWNKYOY-MNYVGDBSSA-N
SmilesO=C(OCC(=CCC=1C(O)=CC=C(C(=O)C=CC2=CC=C(O)C=C2O)C1O)C)C=CC3=CC=C(O)C(OC)=C3
SuperclassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids

Pharmacokinetic properties

Number of descriptor values(#stars)6
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)17
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)532.546
Computed dipole moment(dipole)3.91
Total solvent accessible surface area (SASA)941.42
Hydrophobic component of SASA (FOSA)271.369
Hydrophilic component of SASA (FISA)305.011
Pie component of the SASA (PISA)365.04
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1674.86
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)7.5
Free energy of solvation of dipole (dip^2/V)0.0091276
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0159334
Globularity descriptor (glob)0.724494
Predicted polarizability in cubic angstroms (QPpolrz)53.445
Predicted hexadecane/gas partition coefficient (QPlogPC16)20.079
Predicted octanol/gas partition coefficient (QPlogPoct)28.167
Predicted water/gas partition coefficient (QPlogPw)16.038
Predicted octanol/water partition coefficient (QPlogPo/w)4.393
Predicted aqueous solubility (QPlogS)-7.349
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.849
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.731
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)12.691
Predicted brain/blood partition coefficient (QPlogBB)-4.335
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)4.41
Predicted skin permeability, log Kp (QPlogKp)-4.223
PM3 calculated ionization potential (IP(ev))8.815
PM3 calculated electron affinity (EA(eV))0.726
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)0.704
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)59.459
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)174.436
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)3

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P36544CHRNA7Neuronal acetylcholine receptor protein alpha-7 subunitT34429SEA
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P15121AKR1B1Aldose reductaseT26623SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P11511CYP19A1Cytochrome P450 19A1T13260SEA
P29350PTPN6Protein-tyrosine phosphatase 1CT98264SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
P56817BACE1Beta-secretase 1T79031SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P08581METHepatocyte growth factor receptorT40474SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T34429DI0101Corneal disease[ICD-11: 9A76-9A78]P36544CHRNA7
T34429DI0370Schizophrenia[ICD-11: 6A20]P36544CHRNA7
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
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
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
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
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1

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