Heteroartonin A



Compound IDCDAMM00427
Common nameHeteroartonin A
IUPAC name2-[2,5-dihydroxy-4-methoxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-3-(3-methylbut-2-enyl)chromen-4-one
Molecular formulaC26H28O7

Experimental data

Retention time8.26
Adduct[M+H]+
Actual mz453.198
Theoretical mz453.191
Error13.73
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.5314

Identifiers and class information

Inchi keyONBLHZQNAGITBB-UHFFFAOYSA-N
SmilesO=C1C=2C(O)=CC(O)=CC2OC(C=3C=C(O)C(OC)=C(C3O)CC=C(C)C)=C1CC=C(C)C
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)9
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)452.503
Computed dipole moment(dipole)7.059
Total solvent accessible surface area (SASA)729.53
Hydrophobic component of SASA (FOSA)381.486
Hydrophilic component of SASA (FISA)194.636
Pie component of the SASA (PISA)153.407
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1374.06
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)5.25
Free energy of solvation of dipole (dip^2/V)0.0362616
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0124646
Globularity descriptor (glob)0.81933
Predicted polarizability in cubic angstroms (QPpolrz)44.522
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.103
Predicted octanol/gas partition coefficient (QPlogPoct)22.526
Predicted water/gas partition coefficient (QPlogPw)11.422
Predicted octanol/water partition coefficient (QPlogPo/w)4.188
Predicted aqueous solubility (QPlogS)-5.869
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.081
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.187
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)141.308
Predicted brain/blood partition coefficient (QPlogBB)-1.912
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)59.673
Predicted skin permeability, log Kp (QPlogKp)-3.702
PM3 calculated ionization potential (IP(ev))8.972
PM3 calculated electron affinity (EA(eV))0.454
Number of likely metabolic reactions (#metab)11
Prediction of binding to human serum albumin (QPlogKhsa)0.807
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)89.954
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)123.487
Number of nitrogen and oxygen atoms (#NandO)7
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
Q96KS0EIT6HIF-prolyl hydroxylase 1T53904SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P21397MAOAMonoamine oxidase AT83875SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SwissTargetPrediction and SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P15121AKR1B1Aldose reductaseT26623SEA
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
Q9HC97GPR35G-protein coupled receptor 35T56143SEA
P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
P41145OPRK1Kappa Opioid receptorT60693SwissTargetPrediction
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P06276BCHEButyrylcholinesteraseT99799SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SEA
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P41743PRKCIProtein kinase C iotaT83174SwissTargetPrediction
P05771PRKCBProtein kinase C betaT40276SwissTargetPrediction
P47871GCGRGlucagon receptorT60182SwissTargetPrediction
P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
P03952KLKB1Plasma kallikreinT82739SwissTargetPrediction
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
P14679TYRTyrosinaseT97035SEA
Q9NPH5NOX4NADPH oxidase 4T29741SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q14680MELKMaternal embryonic leucine zipper kinaseT96892SwissTargetPrediction
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
Q04760GLO1Glyoxalase IT88285SEA
P51679CCR4C-C chemokine receptor type 4T06955SwissTargetPrediction
P14625HSP90B1EndoplasminT81311SwissTargetPrediction
O60911CTSVCathepsin (V and K)T93653SEA
Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
P05231IL6Interleukin-6T32578SEA
P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
Q15717ELAVL1ELAV-like protein 1T78349SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA
H3BPQ1TCF4Transcription factor 7-like 2T54646SEA
Q9GZT9EGLN1Egl nine homolog 1T32880SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T53904DI0010Acute disease anaemia[ICD-11: 3A90]Q96KS0EIT6
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
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
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
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
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T60693DI0304Non-specific cutaneous vascular symptom[ICD-11: ME64]P41145OPRK1
T60693DI0324Pain[ICD-11: MG30-MG3Z]P41145OPRK1
T60693DI0349Pruritus[ICD-11: EC90]P41145OPRK1
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
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
T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T83174DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P41743PRKCI
T40276DI0123Diffuse large B-cell lymphoma[ICD-11: 2A81]P05771PRKCB
T40276DI0241Lymphoma[ICD-11: 2A80-2A86]P05771PRKCB
T40276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P05771PRKCB
T60182DI0193Hypo-glycaemia[ICD-11: 5A41]P47871GCGR
T74456DI0137Essential hypertension[ICD-11: BA00]P30556AGTR1
T74456DI0190Hypertension[ICD-11: BA00-BA04]P30556AGTR1
T74456DI0373Secondary hypertension[ICD-11: BA04]P30556AGTR1
T74456DI0425Urinary system clinical symptom[ICD-11: MF8Y]P30556AGTR1
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
T82739DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P03952KLKB1
T82739DI0364Retinal vascular occlusion[ICD-11: 9B74]P03952KLKB1
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
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T96892DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q14680MELK
T96892DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q14680MELK
T96892DI0249Mature B-cell leukaemia[ICD-11: 2A82]Q14680MELK
T96892DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q14680MELK
T96892DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q14680MELK
T96892DI0286Myeloproliferative neoplasm[ICD-11: 2A20]Q14680MELK
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T06955DI0283Mycosis fungoides[ICD-11: 2B01]P51679CCR4
T06955DI0379Sezary syndrome[ICD-11: 2B02]P51679CCR4
T81311DI0238Lung cancer[ICD-11: 2C25]P14625HSP90B1
T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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