Xanthohumol C



Compound IDCDAMM02012
Common nameXanthohumol C
IUPAC name1-(5-hydroxy-7-methoxy-2,2-dimethylchromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Molecular formulaC21H20O5

Experimental data

Retention time0.58
Adduct[M+NH4]+
Actual mz370.163
Theoretical mz370.165
Error4.65
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8673

Identifiers and class information

Inchi keyCVMUWVCGBFJJFI-RMKNXTFCSA-N
SmilesO=C(C=CC1=CC=C(O)C=C1)C2=C(OC)C=C3OC(C=CC3=C2O)(C)C
SuperclassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids

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)7
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)352.386
Computed dipole moment(dipole)6.069
Total solvent accessible surface area (SASA)661.676
Hydrophobic component of SASA (FOSA)247.933
Hydrophilic component of SASA (FISA)126.314
Pie component of the SASA (PISA)287.429
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1144.79
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)4
Free energy of solvation of dipole (dip^2/V)0.0321793
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0060453
Globularity descriptor (glob)0.799838
Predicted polarizability in cubic angstroms (QPpolrz)37.911
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.997
Predicted octanol/gas partition coefficient (QPlogPoct)16.359
Predicted water/gas partition coefficient (QPlogPw)7.986
Predicted octanol/water partition coefficient (QPlogPo/w)4.246
Predicted aqueous solubility (QPlogS)-5.725
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.668
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.142
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)628.157
Predicted brain/blood partition coefficient (QPlogBB)-1.175
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)299.285
Predicted skin permeability, log Kp (QPlogKp)-2.163
PM3 calculated ionization potential (IP(ev))8.825
PM3 calculated electron affinity (EA(eV))0.545
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)0.651
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
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)77.731
Number of nitrogen and oxygen atoms (#NandO)5
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P36544CHRNA7Neuronal acetylcholine receptor protein alpha-7 subunitT34429SwissTargetPrediction
P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
P21397MAOAMonoamine oxidase AT83875SwissTargetPrediction and SEA
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction and SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P27338MAOBMonoamine oxidase BT83011SwissTargetPrediction and SEA
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SwissTargetPrediction and SEA
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P49137MAPKAPK2MAP kinase-activated protein kinase 2T21307SwissTargetPrediction
P13726F3Coagulation factor VII/tissue factorT72702SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P04626ERBB2Receptor protein-tyrosine kinase erbB-2T14597SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P11388TOP2ADNA topoisomerase II alphaT17048SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
Q9NR96TLR9Toll-like receptor (TLR7/TLR9)T11451SEA
Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
P00749PLAUUrokinase-type plasminogen activatorT17758SwissTargetPrediction
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
P14679TYRTyrosinaseT97035SEA
P22001KCNA3Voltage-gated potassium channel subunit Kv1.3T76914SwissTargetPrediction and SEA
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
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
P32249EBI2EBV-induced G-protein coupled receptor 2T59577SEA
P10809HSPD1Mitochondrial matrix protein P1T11283SEA

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
T02703DI0083Chronic kidney disease[ICD-11: GB61]P35228NOS2
T02703DI0320Osteoarthritis[ICD-11: FA00-FA05]P35228NOS2
T02703DI0375Sepsis[ICD-11: 1G40-1G41]P35228NOS2
T02703DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35228NOS2
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
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
T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
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
T21307DI0011Acute laryngitis/tracheitis[ICD-11: CA05]P49137MAPKAPK2
T21307DI0181Hidradenitis suppurativa[ICD-11: ED92]P49137MAPKAPK2
T21307DI0269Monogenic autoinflammatory syndrome[ICD-11: 4A60]P49137MAPKAPK2
T21307DI0334Peritoneal cancer[ICD-11: 2C51]P49137MAPKAPK2
T21307DI0352Psoriatic arthritis[ICD-11: FA21]P49137MAPKAPK2
T21307DI0366Rheumatoid arthritis[ICD-11: FA20]P49137MAPKAPK2
T21307DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P49137MAPKAPK2
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T14597DI0062Breast cancer[ICD-11: 2C60-2C6Y]P04626ERBB2
T14597DI0238Lung cancer[ICD-11: 2C25]P04626ERBB2
T14597DI0346Prostate cancer[ICD-11: 2C82]P04626ERBB2
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T84631DI0053Blood-forming organ disease[ICD-11: 3C0Z]P00742F10
T84631DI0080Christmas disease[ICD-11: 3B11]P00742F10
T84631DI0091Coagulation defect[ICD-11: 3B10]P00742F10
T84631DI0103Coronary thrombosis[ICD-11: BA43]P00742F10
T84631DI0114Deep vein thrombosis[ICD-11: BD71]P00742F10
T84631DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P00742F10
T84631DI0405Thrombosis[ICD-11: DB61-GB90]P00742F10
T84631DI0433Venous thromboembolism[ICD-11: BD72]P00742F10
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T11451DI0095Colorectal cancer[ICD-11: 2B91]Q9NR96TLR9
T11451DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]Q9NR96TLR9
T11451DI0252Melanoma[ICD-11: 2C30]Q9NR96TLR9
T11451DI0346Prostate cancer[ICD-11: 2C82]Q9NR96TLR9
T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
T17758DI0211Inherited coagulation factor deficiency[ICD-11: 3B14]P00749PLAU
T17758DI0287Myocardial infarction[ICD-11: BA41-BA43]P00749PLAU
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T76914DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P22001KCNA3
T76914DI0351Psoriasis[ICD-11: EA90]P22001KCNA3
T76914DI0352Psoriatic arthritis[ICD-11: FA21]P22001KCNA3
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
T11283DI0120Diabetes mellitus[ICD-11: 5A10]P10809HSPD1

Copyright © 2025