(E)-4-(3,7-Dimethyl-2,6-octadienyl)-1,3,5-trihydroxyxanthone



Compound IDCDAMM01571
Common name(E)-4-(3,7-Dimethyl-2,6-octadienyl)-1,3,5-trihydroxyxanthone
IUPAC name4-(3,7-dimethylocta-2,6-dienyl)-1,3,5-trihydroxyxanthen-9-one
Molecular formulaC23H24O5

Experimental data

Retention time7.41
Adduct[M+H]+
Actual mz381.17
Theoretical mz381.169
Error2.95
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9958

Identifiers and class information

Inchi keyPCKHKINJZFNYEO-UVTDQMKNSA-N
SmilesO=C1C=2C=CC=C(O)C2OC=3C1=C(O)C=C(O)C3CC=C(C)CCC=C(C)C
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

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)8
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)380.44
Computed dipole moment(dipole)4.269
Total solvent accessible surface area (SASA)662.754
Hydrophobic component of SASA (FOSA)303.747
Hydrophilic component of SASA (FISA)145.253
Pie component of the SASA (PISA)213.754
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1209.22
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)3.75
Free energy of solvation of dipole (dip^2/V)0.0150683
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0080019
Globularity descriptor (glob)0.828228
Predicted polarizability in cubic angstroms (QPpolrz)39.144
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.435
Predicted octanol/gas partition coefficient (QPlogPoct)17.95
Predicted water/gas partition coefficient (QPlogPw)8.614
Predicted octanol/water partition coefficient (QPlogPo/w)4.358
Predicted aqueous solubility (QPlogS)-5.507
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.182
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.331
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)415.399
Predicted brain/blood partition coefficient (QPlogBB)-1.33
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)191.406
Predicted skin permeability, log Kp (QPlogKp)-2.675
PM3 calculated ionization potential (IP(ev))9.08
PM3 calculated electron affinity (EA(eV))0.654
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)0.763
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)93.541
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
P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
P21397MAOAMonoamine oxidase AT83875SEA
P14416DRD2Dopamine D2 receptorT67162SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SwissTargetPrediction and SEA
P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P51681CCR5C-C chemokine receptor type 5T09960SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction and SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction
P35372OPRM1Mu opioid receptorT47768SwissTargetPrediction
P41145OPRK1Kappa Opioid receptorT60693SwissTargetPrediction
P04626ERBB2Receptor protein-tyrosine kinase erbB-2T14597SwissTargetPrediction
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P11802CDK4Cyclin-dependent kinase 4T85799SwissTargetPrediction
P49327FASNFatty acid synthaseT16514SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
P11137MAP2Microtubule-associated protein 2T23276SwissTargetPrediction
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
P08238HSP90AB1Heat shock protein HSP 90-betaT96623SwissTargetPrediction
P35222CTNNB1Axin1/beta-cateninT82795SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P41743PRKCIProtein kinase C iotaT83174SwissTargetPrediction
P47871GCGRGlucagon receptorT60182SwissTargetPrediction
P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
Q96EB6SIRT1NAD-dependent deacetylase sirtuin 1T14731SwissTargetPrediction
P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
P00749PLAUUrokinase-type plasminogen activatorT17758SwissTargetPrediction
O14980XPO1Exportin-1T51407SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction
P51812RPS6KA3Ribosomal protein S6 kinase alpha 3T03279SwissTargetPrediction
Q16549PCSK7Subtilisin/kexin type 7T33211SEA
P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
Q14680MELKMaternal embryonic leucine zipper kinaseT96892SwissTargetPrediction
P51679CCR4C-C chemokine receptor type 4T06955SwissTargetPrediction
P14625HSP90B1EndoplasminT81311SwissTargetPrediction
O60911CTSVCathepsin (V and K)T93653SEA
Q00534CDK6Cyclin-dependent kinase 6T89361SwissTargetPrediction
P06881CALCACalcitonin gene-related peptide 1T93509SwissTargetPrediction
P41586ADCYAP1R1Pituitary adenylate cyclase-activating polypeptide type I receptorT92185SwissTargetPrediction
O95749GGPS1GeranyltranstransferaseT86528SEA
Q15717ELAVL1ELAV-like protein 1T78349SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
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
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T40016DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P04150NR3C1
T40016DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P04150NR3C1
T40016DI0037Asthma[ICD-11: CA23]P04150NR3C1
T40016DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P04150NR3C1
T40016DI0108Cushing syndrome[ICD-11: 5A70]P04150NR3C1
T40016DI0280Muscular dystrophy[ICD-11: 8C70]P04150NR3C1
T40016DI0314Oesophagitis[ICD-11: DA24]P04150NR3C1
T40016DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P04150NR3C1
T40016DI0366Rheumatoid arthritis[ICD-11: FA20]P04150NR3C1
T40016DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04150NR3C1
T40016DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P04150NR3C1
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T09960DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P51681CCR5
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
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T47768DI0013Acute pain[ICD-11: MG31]P35372OPRM1
T47768DI0059Bowel habit change[ICD-11: ME05]P35372OPRM1
T47768DI0087Chronic pain[ICD-11: MG30]P35372OPRM1
T47768DI0101Corneal disease[ICD-11: 9A76-9A78]P35372OPRM1
T47768DI0105Cough[ICD-11: MD12]P35372OPRM1
T47768DI0117Depression[ICD-11: 6A70-6A7Z]P35372OPRM1
T47768DI0124Digestive system disease[ICD-11: DE2Z]P35372OPRM1
T47768DI0218Irritable bowel syndrome[ICD-11: DD91]P35372OPRM1
T47768DI0228Large intestine motility disorder[ICD-11: DB32]P35372OPRM1
T47768DI0317Opioid use disorder[ICD-11: 6C43]P35372OPRM1
T47768DI0324Pain[ICD-11: MG30-MG3Z]P35372OPRM1
T47768DI0349Pruritus[ICD-11: EC90]P35372OPRM1
T47768DI0374Sensation disturbance[ICD-11: MB40]P35372OPRM1
T60693DI0304Non-specific cutaneous vascular symptom[ICD-11: ME64]P41145OPRK1
T60693DI0324Pain[ICD-11: MG30-MG3Z]P41145OPRK1
T60693DI0349Pruritus[ICD-11: EC90]P41145OPRK1
T14597DI0062Breast cancer[ICD-11: 2C60-2C6Y]P04626ERBB2
T14597DI0238Lung cancer[ICD-11: 2C25]P04626ERBB2
T14597DI0346Prostate cancer[ICD-11: 2C82]P04626ERBB2
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T85799DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11802CDK4
T85799DI0238Lung cancer[ICD-11: 2C25]P11802CDK4
T85799DI0351Psoriasis[ICD-11: EA90]P11802CDK4
T16514DI0096concerning food/fluid intake symptom[ICD-11: MG43]P49327FASN
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
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
T02001DI0411Tonus and reflex abnormality[ICD-11: MB47]Q08499PDE4D
T23276DI0036Arteries/arterioles disorder[ICD-11: BD52]P11137MAP2
T23276DI0252Melanoma[ICD-11: 2C30]P11137MAP2
T23276DI0326Pancreatic cancer[ICD-11: 2C10]P11137MAP2
T23276DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11137MAP2
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
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
T82795DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35222CTNNB1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T83174DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P41743PRKCI
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
T14731DI0366Rheumatoid arthritis[ICD-11: FA20]Q96EB6SIRT1
T14731DI0399Systemic sclerosis[ICD-11: 4A42]Q96EB6SIRT1
T14731DI0431Vasculitis[ICD-11: 4A44]Q96EB6SIRT1
T49898DI0062Breast cancer[ICD-11: 2C60-2C6Y]P06493CDK1
T49898DI0238Lung cancer[ICD-11: 2C25]P06493CDK1
T49898DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P06493CDK1
T49898DI0250Mature B-cell lymphoma[ICD-11: 2A85]P06493CDK1
T49898DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06493CDK1
T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
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
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
T17758DI0211Inherited coagulation factor deficiency[ICD-11: 3B14]P00749PLAU
T17758DI0287Myocardial infarction[ICD-11: BA41-BA43]P00749PLAU
T51407DI0234Liposarcoma[ICD-11: 2B59]O14980XPO1
T51407DI0274Multiple myeloma[ICD-11: 2A83]O14980XPO1
T51407DI0395Stomach cancer[ICD-11: 2B72]O14980XPO1
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T03279DI0249Mature B-cell leukaemia[ICD-11: 2A82]P51812RPS6KA3
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
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
T89361DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q00534CDK6
T89361DI0238Lung cancer[ICD-11: 2C25]Q00534CDK6
T89361DI0351Psoriasis[ICD-11: EA90]Q00534CDK6
T93509DI0163General pain disorder[ICD-11: 8E43]P06881CALCA
T92185DI0264Migraine[ICD-11: 8A80]P41586ADCYAP1R1
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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