2\',4\',6\',3-Tetrahydroxy-3\'-geranyl-6\'\',6\'\'-dimethylpyrano[2\'\',3\'\':4,5]dihydrochalcone



Compound IDCDAMM02762
Common name2\',4\',6\',3-Tetrahydroxy-3\'-geranyl-6\'\',6\'\'-dimethylpyrano[2\'\',3\'\':4,5]dihydrochalcone
IUPAC name1-[3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl]-3-(8-hydroxy-2,2-dimethylchromen-6-yl)propan-1-one
Molecular formulaC30H36O6

Experimental data

Retention time12.54
Adduct[M+K]+
Actual mz531.218
Theoretical mz531.214
Error7.99
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.4133

Identifiers and class information

Inchi keyLEVMXFZLHWQXFZ-DJKKODMXSA-N
SmilesO=C(C1=C(O)C=C(O)C(=C1O)CC=C(C)CCC=C(C)C)CCC=2C=C(O)C=3OC(C=CC3C2)(C)C
SuperclassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids

Pharmacokinetic properties

Number of descriptor values(#stars)5
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)13
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)492.611
Computed dipole moment(dipole)8.323
Total solvent accessible surface area (SASA)918.146
Hydrophobic component of SASA (FOSA)524.961
Hydrophilic component of SASA (FISA)181.366
Pie component of the SASA (PISA)211.819
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1653.83
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)3.75
Free energy of solvation of dipole (dip^2/V)0.0418896
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0057761
Globularity descriptor (glob)0.736627
Predicted polarizability in cubic angstroms (QPpolrz)53.708
Predicted hexadecane/gas partition coefficient (QPlogPC16)17.326
Predicted octanol/gas partition coefficient (QPlogPoct)23.118
Predicted water/gas partition coefficient (QPlogPw)8.359
Predicted octanol/water partition coefficient (QPlogPo/w)6.908
Predicted aqueous solubility (QPlogS)-9.31
Conformation-independent predicted aqueous solubility (CIQPlogS)-8.541
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.804
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)188.8
Predicted brain/blood partition coefficient (QPlogBB)-2.448
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)81.62
Predicted skin permeability, log Kp (QPlogKp)-2.868
PM3 calculated ionization potential (IP(ev))8.787
PM3 calculated electron affinity (EA(eV))0.219
Number of likely metabolic reactions (#metab)12
Prediction of binding to human serum albumin (QPlogKhsa)1.745
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)95.169
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)112.657
Number of nitrogen and oxygen atoms (#NandO)6
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
P09874PARP1Poly [ADP-ribose] polymerase-1T06273SwissTargetPrediction
P04818TYMSThymidylate synthase (by homology)T98397SwissTargetPrediction
P00734F2ThrombinT94033SwissTargetPrediction
P08514ITGA2BIntegrin alpha-IIb/beta-3T50688SwissTargetPrediction
P00747PLGPlasminogenT89034SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SwissTargetPrediction and SEA
P10275ARAndrogen ReceptorT11211SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
Q13547HDAC1Histone deacetylase 1T68547SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
P13726F3Coagulation factor VII/tissue factorT72702SwissTargetPrediction
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P30291WEE1Serine/threonine-protein kinase WEE1T69991SwissTargetPrediction
P36888FLT3Tyrosine-protein kinase receptor FLT3T74312SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P78536ADAM17ADAM17T82393SwissTargetPrediction
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SwissTargetPrediction
P07333CSF1RMacrophage colony stimulating factor receptorT20333SwissTargetPrediction
O00763ACACBAcetyl-CoA carboxylase 2T08922SwissTargetPrediction
P32239CCKBRCholecystokinin B receptor (by homology)T05849SwissTargetPrediction
P03952KLKB1Plasma kallikreinT82739SwissTargetPrediction
P32418SLC8A1Sodium/calcium exchanger 1T07775SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
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
T06273DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P09874PARP1
T06273DI0143Fallopian tube cancer[ICD-11: 2C74]P09874PARP1
T06273DI0321Ovarian cancer[ICD-11: 2C73]P09874PARP1
T06273DI0334Peritoneal cancer[ICD-11: 2C51]P09874PARP1
T98397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04818TYMS
T98397DI0395Stomach cancer[ICD-11: 2B72]P04818TYMS
T94033DI0052Bleeding disorder[ICD-11: GA20-GA21]P00734F2
T94033DI0091Coagulation defect[ICD-11: 3B10]P00734F2
T94033DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P00734F2
T94033DI0275Multiple sclerosis[ICD-11: 8A40]P00734F2
T94033DI0287Myocardial infarction[ICD-11: BA41-BA43]P00734F2
T94033DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00734F2
T94033DI0403Thrombocytopenia[ICD-11: 3B64]P00734F2
T94033DI0405Thrombosis[ICD-11: DB61-GB90]P00734F2
T50688DI0007Acquired hypermelanosis[ICD-11: ED60]P08514ITGA2B
T50688DI0030Angina pectoris[ICD-11: BA40]P08514ITGA2B
T50688DI0287Myocardial infarction[ICD-11: BA41-BA43]P08514ITGA2B
T89034DI0030Angina pectoris[ICD-11: BA40]P00747PLG
T89034DI0052Bleeding disorder[ICD-11: GA20-GA21]P00747PLG
T89034DI0254Menopausal disorder[ICD-11: GA30]P00747PLG
T89034DI0287Myocardial infarction[ICD-11: BA41-BA43]P00747PLG
T89034DI0345Procedure injury[ICD-11: NE81]P00747PLG
T89034DI0357Pulmonary thromboembolism[ICD-11: BB00]P00747PLG
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T11211DI0005Acne vulgaris[ICD-11: ED80]P10275AR
T11211DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10275AR
T11211DI0021Alcoholic liver disease[ICD-11: DB94]P10275AR
T11211DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10275AR
T11211DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P10275AR
T11211DI0145Female pelvic pain[ICD-11: GA34]P10275AR
T11211DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P10275AR
T11211DI0237Low bone mass disorder[ICD-11: FB83]P10275AR
T11211DI0247Mammary tumour[ICD-11: 2C60-2C6Z]P10275AR
T11211DI0346Prostate cancer[ICD-11: 2C82]P10275AR
T11211DI0401Testicular dysfunction[ICD-11: 5A81]P10275AR
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
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
T68547DI0274Multiple myeloma[ICD-11: 2A83]Q13547HDAC1
T68547DI0283Mycosis fungoides[ICD-11: 2B01]Q13547HDAC1
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T69991DI0321Ovarian cancer[ICD-11: 2C73]P30291WEE1
T69991DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P30291WEE1
T69991DI0429Uterine ligament/parametrium/uterine adnexa neoplasm[ICD-11: 2C72]P30291WEE1
T74312DI0012Acute myeloid leukaemia[ICD-11: 2A60]P36888FLT3
T74312DI0058Bone/articular cartilage neoplasm[ICD-11: 2F7B]P36888FLT3
T74312DI0095Colorectal cancer[ICD-11: 2B91]P36888FLT3
T74312DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P36888FLT3
T74312DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P36888FLT3
T74312DI0248Mastocytosis[ICD-11: 2A21]P36888FLT3
T74312DI0250Mature B-cell lymphoma[ICD-11: 2A85]P36888FLT3
T74312DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P36888FLT3
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
T84133DI0079Choreiform disorder[ICD-11: 8A01]Q9Y233PDE10A
T84133DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q9Y233PDE10A
T84133DI0218Irritable bowel syndrome[ICD-11: DD91]Q9Y233PDE10A
T84133DI0370Schizophrenia[ICD-11: 6A20]Q9Y233PDE10A
T84133DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9Y233PDE10A
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
T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
T20333DI0058Bone/articular cartilage neoplasm[ICD-11: 2F7B]P07333CSF1R
T08922DI0417Type 2 diabetes mellitus[ICD-11: 5A11]O00763ACACB
T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
T82739DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P03952KLKB1
T82739DI0364Retinal vascular occlusion[ICD-11: 9B74]P03952KLKB1

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