3-Geranyl-4,2\',4\',6\'-tetrahydroxy-5-prenyldihydrochalcone



Compound IDCDAMM02209
Common name3-Geranyl-4,2\',4\',6\'-tetrahydroxy-5-prenyldihydrochalcone
IUPAC name3-[3-(3,7-dimethylocta-2,6-dienyl)-4-hydroxy-5-(3-methylbut-2-enyl)phenyl]-1-(2,4,6-trihydroxyphenyl)propan-1-one
Molecular formulaC30H38O5

Experimental data

Retention time8.47
Adduct[M+H]+
Actual mz479.279
Theoretical mz479.279
Error0.37
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.1532

Identifiers and class information

Inchi keyWXQUELGXSBNBPD-UFFVCSGVSA-N
SmilesO=C(C=1C(O)=CC(O)=CC1O)CCC=2C=C(C(O)=C(C2)CC=C(C)CCC=C(C)C)CC=C(C)C
SuperclassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids

Pharmacokinetic properties

Number of descriptor values(#stars)4
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)15
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)478.627
Computed dipole moment(dipole)6.167
Total solvent accessible surface area (SASA)796.417
Hydrophobic component of SASA (FOSA)530.545
Hydrophilic component of SASA (FISA)139.796
Pie component of the SASA (PISA)126.076
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1587.89
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)3
Free energy of solvation of dipole (dip^2/V)0.0239504
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0053272
Globularity descriptor (glob)0.826489
Predicted polarizability in cubic angstroms (QPpolrz)48.966
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.139
Predicted octanol/gas partition coefficient (QPlogPoct)20.856
Predicted water/gas partition coefficient (QPlogPw)6.02
Predicted octanol/water partition coefficient (QPlogPo/w)7.01
Predicted aqueous solubility (QPlogS)-7.026
Conformation-independent predicted aqueous solubility (CIQPlogS)-8.37
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.941
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)467.964
Predicted brain/blood partition coefficient (QPlogBB)-1.705
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)217.715
Predicted skin permeability, log Kp (QPlogKp)-2.212
PM3 calculated ionization potential (IP(ev))8.76
PM3 calculated electron affinity (EA(eV))0.042
Number of likely metabolic reactions (#metab)15
Prediction of binding to human serum albumin (QPlogKhsa)1.65
Predicted qualitative human oral absorption (HumanOralAbsorption)1
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)105.338
Number of nitrogen and oxygen atoms (#NandO)5
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
O15379HDAC3Histone deacetylase 3T05090SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P14416DRD2Dopamine D2 receptorT67162SwissTargetPrediction
P21554CNR1Cannabinoid receptor 1 (by homology)T76685SwissTargetPrediction
P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
Q9UKV0HDAC9Histone deacetylase 9T03687SwissTargetPrediction
P43235CTSKCathepsin KT11388SwissTargetPrediction
Q9UBN7HDAC6Histone deacetylase 6T22274SwissTargetPrediction
P07384CAPN1Calpain 1T92517SwissTargetPrediction
Q92769HDAC2Histone deacetylase 2T51191SwissTargetPrediction
Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
O00519FAAHAnandamide amidohydrolaseT11754SwissTargetPrediction
P51681CCR5C-C chemokine receptor type 5T09960SwissTargetPrediction
O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
Q13547HDAC1Histone deacetylase 1T68547SwissTargetPrediction
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
Q9BY41HDAC8Histone deacetylase 8T28887SwissTargetPrediction
Q14534SQLESqualene monooxygenase (by homology)T93344SEA
P35462DRD3Dopamine D3 receptorT02551SwissTargetPrediction
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P78536ADAM17ADAM17T82393SwissTargetPrediction
P08172CHRM2Muscarinic acetylcholine receptor M2T46185SwissTargetPrediction
P07711CTSLCathepsin LT98691SwissTargetPrediction
P32245MC4RMelanocortin receptor 4T72458SwissTargetPrediction
P23458JAK1Tyrosine-protein kinase JAK1T62460SwissTargetPrediction
P08238HSP90AB1Heat shock protein HSP 90-betaT96623SwissTargetPrediction
P35916FLT4Vascular endothelial growth factor receptor 3T07303SwissTargetPrediction
P52333JAK3Tyrosine-protein kinase JAK3T23172SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
P25929NPY1RNeuropeptide Y receptor type 1T89213SwissTargetPrediction
P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
P32238CCKARCholecystokinin A receptorT28330SwissTargetPrediction
Q16602CALCRLCalcitonin gene-related peptide type 1 receptorT02226SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
P53582METAP1Methionine aminopeptidase 1T42337SwissTargetPrediction
P55157MTTPMicrosomal triglyceride transfer protein large subunitT46628SwissTargetPrediction
Q9Y345SLC6A5Glycine transporter 2T58937SwissTargetPrediction
O95749GGPS1GeranyltranstransferaseT86528SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T05090DI0241Lymphoma[ICD-11: 2A80-2A86]O15379HDAC3
T05090DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O15379HDAC3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T67162DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P14416DRD2
T67162DI0025Alzheimer disease[ICD-11: 8A20]P14416DRD2
T67162DI0037Asthma[ICD-11: CA23]P14416DRD2
T67162DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P14416DRD2
T67162DI0051Bipolar disorder[ICD-11: 6A60]P14416DRD2
T67162DI0063Breathing abnormality[ICD-11: MD11]P14416DRD2
T67162DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P14416DRD2
T67162DI0073Cerebral ischaemia[ICD-11: 8B1Z]P14416DRD2
T67162DI0117Depression[ICD-11: 6A70-6A7Z]P14416DRD2
T67162DI0124Digestive system disease[ICD-11: DE2Z]P14416DRD2
T67162DI0137Essential hypertension[ICD-11: BA00]P14416DRD2
T67162DI0142Faecal incontinence[ICD-11: ME07]P14416DRD2
T67162DI0156Gangrene[ICD-11: MC85]P14416DRD2
T67162DI0166Glaucoma[ICD-11: 9C61]P14416DRD2
T67162DI0175Heart failure[ICD-11: BD10-BD1Z]P14416DRD2
T67162DI0185Hyperaemia[ICD-11: 9A61-9B7Y]P14416DRD2
T67162DI0190Hypertension[ICD-11: BA00-BA04]P14416DRD2
T67162DI0196Hypotension[ICD-11: BA20-BA21]P14416DRD2
T67162DI0205Inborn porphyrin/heme metabolism error[ICD-11: 5C58]P14416DRD2
T67162DI0214Insomnia[ICD-11: 7A00-7A0Z]P14416DRD2
T67162DI0222Itching[ICD-11: 1F28-1G07]P14416DRD2
T67162DI0264Migraine[ICD-11: 8A80]P14416DRD2
T67162DI0293Nausea/vomiting[ICD-11: MD90]P14416DRD2
T67162DI0324Pain[ICD-11: MG30-MG3Z]P14416DRD2
T67162DI0331Parkinsonism[ICD-11: 8A00]P14416DRD2
T67162DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P14416DRD2
T67162DI0340Postpartum haemorrhage[ICD-11: JA43]P14416DRD2
T67162DI0354Psychotic disorder[ICD-11: 6A20-6A25]P14416DRD2
T67162DI0356Pulmonary hypertension[ICD-11: BB01]P14416DRD2
T67162DI0370Schizophrenia[ICD-11: 6A20]P14416DRD2
T67162DI0396Substance abuse[ICD-11: 6C40]P14416DRD2
T67162DI0408Thyrotoxicosis[ICD-11: 5A02]P14416DRD2
T67162DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P14416DRD2
T76685DI0031Anorexia nervosa[ICD-11: 6B80]P21554CNR1
T76685DI0214Insomnia[ICD-11: 7A00-7A0Z]P21554CNR1
T76685DI0308Obesity[ICD-11: 5B80-5B81]P21554CNR1
T27812DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P31645SLC6A4
T27812DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P31645SLC6A4
T27812DI0087Chronic pain[ICD-11: MG30]P31645SLC6A4
T27812DI0096concerning food/fluid intake symptom[ICD-11: MG43]P31645SLC6A4
T27812DI0101Corneal disease[ICD-11: 9A76-9A78]P31645SLC6A4
T27812DI0105Cough[ICD-11: MD12]P31645SLC6A4
T27812DI0117Depression[ICD-11: 6A70-6A7Z]P31645SLC6A4
T27812DI0264Migraine[ICD-11: 8A80]P31645SLC6A4
T27812DI0301Nicotine use disorder[ICD-11: 6C4A]P31645SLC6A4
T27812DI0308Obesity[ICD-11: 5B80-5B81]P31645SLC6A4
T27812DI0324Pain[ICD-11: MG30-MG3Z]P31645SLC6A4
T11388DI0237Low bone mass disorder[ICD-11: FB83]P43235CTSK
T22274DI0274Multiple myeloma[ICD-11: 2A83]Q9UBN7HDAC6
T22274DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UBN7HDAC6
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
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
T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
T11754DI0101Corneal disease[ICD-11: 9A76-9A78]O00519FAAH
T09960DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P51681CCR5
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T68547DI0274Multiple myeloma[ICD-11: 2A83]Q13547HDAC1
T68547DI0283Mycosis fungoides[ICD-11: 2B01]Q13547HDAC1
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T28887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9BY41HDAC8
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T02551DI0051Bipolar disorder[ICD-11: 6A60]P35462DRD3
T02551DI0331Parkinsonism[ICD-11: 8A00]P35462DRD3
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
T46185DI0037Asthma[ICD-11: CA23]P08172CHRM2
T46185DI0166Glaucoma[ICD-11: 9C61]P08172CHRM2
T46185DI0278Muscle disorder[ICD-11: FB32-FB3Z]P08172CHRM2
T46185DI0333Peptic ulcer[ICD-11: DA61]P08172CHRM2
T46185DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08172CHRM2
T46185DI0371Sebaceous gland disorder[ICD-11: ED91]P08172CHRM2
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
T62460DI0039Atopic eczema[ICD-11: EA80]P23458JAK1
T62460DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P23458JAK1
T62460DI0366Rheumatoid arthritis[ICD-11: FA20]P23458JAK1
T62460DI0404Thrombocytosis[ICD-11: 3B63]P23458JAK1
T96623DI0062Breast cancer[ICD-11: 2C60-2C6Y]P08238HSP90AB1
T96623DI0238Lung cancer[ICD-11: 2C25]P08238HSP90AB1
T96623DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P08238HSP90AB1
T96623DI0249Mature B-cell leukaemia[ICD-11: 2A82]P08238HSP90AB1
T96623DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P08238HSP90AB1
T96623DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P08238HSP90AB1
T96623DI0395Stomach cancer[ICD-11: 2B72]P08238HSP90AB1
T07303DI0361Renal cell carcinoma[ICD-11: 2C90]P35916FLT4
T23172DI0023Alopecia[ICD-11: ED70]P52333JAK3
T23172DI0039Atopic eczema[ICD-11: EA80]P52333JAK3
T23172DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P52333JAK3
T23172DI0366Rheumatoid arthritis[ICD-11: FA20]P52333JAK3
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T89213DI0050Binge eating disorder[ICD-11: 6B82]P25929NPY1R
T89213DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25929NPY1R
T89213DI0174Heart disease[ICD-11: BA41-BA42]P25929NPY1R
T89213DI0190Hypertension[ICD-11: BA00-BA04]P25929NPY1R
T89213DI0308Obesity[ICD-11: 5B80-5B81]P25929NPY1R
T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
T28330DI0210Influenza[ICD-11: 1E30-1E32]P32238CCKAR
T28330DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P32238CCKAR
T46628DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P55157MTTP
T86528DI0057Bone paget disease[ICD-11: FB85]O95749GGPS1
T86528DI0237Low bone mass disorder[ICD-11: FB83]O95749GGPS1
T86528DI0267Mineral excesses[ICD-11: 5B91]O95749GGPS1
T86528DI0281Musculoskeletal disorder[ICD-11: FA00-FC0Z]O95749GGPS1

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