4,6\'-Epoxyorotiniflavan-4-ol



Compound IDCDAMM00600
Common name4,6\'-Epoxyorotiniflavan-4-ol
IUPAC name3-methoxy-7,7-dimethyl-10-(3-methylbut-2-enyl)-8,12,20-trioxapentacyclo[11.7.1.02,11.04,9.014,19]henicosa-2,4(9),5,10,14,16,18-heptaene-1,15-diol
Molecular formulaC26H28O6

Experimental data

Retention time13.46
Adduct[M+H]+
Actual mz437.192
Theoretical mz437.196
Error9.78
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7055

Identifiers and class information

Inchi keyOHXCIEXSFNBDTK-LOUQGOMINA-N
SmilesOC1=CC=CC=2OC3(O)C4=C(OC)C=5C=CC(OC5C(=C4OC(C12)C3)CC=C(C)C)(C)C
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

Plant source

  • Piper longum L.

    • 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)5
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)0
    Molecular weight (mol_MW)436.504
    Computed dipole moment(dipole)4.119
    Total solvent accessible surface area (SASA)654.656
    Hydrophobic component of SASA (FOSA)403.684
    Hydrophilic component of SASA (FISA)66.751
    Pie component of the SASA (PISA)184.22
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1278.35
    Number of hydrogen bond donors (donorHB)2
    Number of hydrogen bond acceptors (accptHB)4.5
    Free energy of solvation of dipole (dip^2/V)0.0132744
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0097211
    Globularity descriptor (glob)0.870133
    Predicted polarizability in cubic angstroms (QPpolrz)43.554
    Predicted hexadecane/gas partition coefficient (QPlogPC16)12.309
    Predicted octanol/gas partition coefficient (QPlogPoct)19.727
    Predicted water/gas partition coefficient (QPlogPw)9.261
    Predicted octanol/water partition coefficient (QPlogPo/w)5.029
    Predicted aqueous solubility (QPlogS)-5.621
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.201
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.512
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2306.21
    Predicted brain/blood partition coefficient (QPlogBB)-0.326
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1220.68
    Predicted skin permeability, log Kp (QPlogKp)-1.621
    PM3 calculated ionization potential (IP(ev))8.782
    PM3 calculated electron affinity (EA(eV))0.315
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)0.965
    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)64.781
    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)1

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
    P09874PARP1Poly [ADP-ribose] polymerase-1T06273SwissTargetPrediction
    P42336PIK3CAPI3-kinase p110-alpha subunitT80276SwissTargetPrediction
    P43405SYKTyrosine-protein kinase SYKT62431SwissTargetPrediction
    P07949RETKinesin-1 heavy chain/ Tyrosine-protein kinase receptor RETT60631SwissTargetPrediction
    P24864CCNE1Cyclin-dependent kinase 2/cyclin E1T10052SwissTargetPrediction
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    P07384CAPN1Calpain 1T92517SwissTargetPrediction
    P11926ODC1Ornithine decarboxylaseT60366SwissTargetPrediction and SEA
    P10275ARAndrogen ReceptorT11211SwissTargetPrediction
    P08235NR3C2Mineralocorticoid receptorT72168SwissTargetPrediction
    P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
    P06401PGRProgesterone receptorT22939SwissTargetPrediction
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
    P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P21964COMTCatechol O-methyltransferase (by homology)T76904SwissTargetPrediction
    P42345MTORSerine/threonine-protein kinase mTORT75243SwissTargetPrediction
    O14757CHEK1Serine/threonine-protein kinase Chk1T62449SwissTargetPrediction
    P00519ABL1Tyrosine-protein kinase ABLT63505SwissTargetPrediction
    P30291WEE1Serine/threonine-protein kinase WEE1T69991SwissTargetPrediction
    Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
    P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
    O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
    Q9NZJ5EIF2AK3Eukaryotic translation initiation factor 2-alpha kinase 3T13176SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P13497BMP1Bone morphogenetic protein 1T53350SwissTargetPrediction
    P11137MAP2Microtubule-associated protein 2T23276SwissTargetPrediction
    P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
    Q15858SCN9ASodium channel protein type IX alpha subunitT12119SwissTargetPrediction
    O00329PIK3CDPI3-kinase p110-delta subunitT67849SwissTargetPrediction
    P29466CASP1Caspase-1T98269SwissTargetPrediction
    P28482MAPK1MAP kinase ERK2T58970SwissTargetPrediction
    P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
    P25101EDNRAEndothelin receptor ET-AT23499SwissTargetPrediction
    Q07912TNK2Tyrosine kinase non-receptor protein 2T63220SwissTargetPrediction
    P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
    P42574CASP3Caspase-3T57943SwissTargetPrediction
    P55210CASP7Caspase-7T72252SwissTargetPrediction
    P34998CRHR1Corticotropin releasing factor receptor 1 (by homology)T45262SwissTargetPrediction
    P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
    P55212CASP6Caspase-6T20600SwissTargetPrediction
    Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
    P48736PIK3CGPI3-kinase p110-gamma subunitT95913SwissTargetPrediction
    Q9UQM7CAMK2ACaM kinase II alphaT18299SwissTargetPrediction
    P46663BDKRB1Bradykinin B1 receptorT58589SwissTargetPrediction
    P14679TYRTyrosinaseT97035SEA
    P55201BRPF1PeregrinT41145SwissTargetPrediction
    Q07343PDE4BPhosphodiesterase 4B (by homology)T10265SwissTargetPrediction
    Q99500S1PR3Sphingosine 1-phosphate receptor Edg-3T11241SwissTargetPrediction

    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
    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
    T80276DI0062Breast cancer[ICD-11: 2C60-2C6Y]P42336PIK3CA
    T80276DI0151Follicular lymphoma[ICD-11: 2A80]P42336PIK3CA
    T80276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P42336PIK3CA
    T62431DI0403Thrombocytopenia[ICD-11: 3B64]P43405SYK
    T60631DI0095Colorectal cancer[ICD-11: 2B91]P07949RET
    T60631DI0238Lung cancer[ICD-11: 2C25]P07949RET
    T60631DI0250Mature B-cell lymphoma[ICD-11: 2A85]P07949RET
    T60631DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P07949RET
    T60631DI0403Thrombocytopenia[ICD-11: 3B64]P07949RET
    T60631DI0407Thyroid cancer[ICD-11: 2D10]P07949RET
    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
    T72168DI0018Adrenocortical insufficiency[ICD-11: 5A74]P08235NR3C2
    T72168DI0083Chronic kidney disease[ICD-11: GB61]P08235NR3C2
    T72168DI0100Contraceptive management[ICD-11: QA21]P08235NR3C2
    T72168DI0175Heart failure[ICD-11: BD10-BD1Z]P08235NR3C2
    T72168DI0190Hypertension[ICD-11: BA00-BA04]P08235NR3C2
    T72168DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P08235NR3C2
    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
    T22939DI0062Breast cancer[ICD-11: 2C60-2C6Y]P06401PGR
    T22939DI0100Contraceptive management[ICD-11: QA21]P06401PGR
    T22939DI0255Menstrual cycle bleeding disorder[ICD-11: GA20]P06401PGR
    T22939DI0344Preterm labour/delivery[ICD-11: JB00]P06401PGR
    T22939DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06401PGR
    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
    T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
    T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
    T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    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
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T76904DI0331Parkinsonism[ICD-11: 8A00]P21964COMT
    T75243DI0036Arteries/arterioles disorder[ICD-11: BD52]P42345MTOR
    T75243DI0085Chronic myelomonocytic leukaemia[ICD-11: 2A40]P42345MTOR
    T75243DI0274Multiple myeloma[ICD-11: 2A83]P42345MTOR
    T75243DI0361Renal cell carcinoma[ICD-11: 2C90]P42345MTOR
    T75243DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P42345MTOR
    T75243DI0413Transplant rejection[ICD-11: NE84]P42345MTOR
    T62449DI0027Anal cancer[ICD-11: 2C00]O14757CHEK1
    T62449DI0172Head and neck cancer[ICD-11: 2D42]O14757CHEK1
    T62449DI0183Hodgkin lymphoma[ICD-11: 2B30]O14757CHEK1
    T62449DI0238Lung cancer[ICD-11: 2C25]O14757CHEK1
    T62449DI0241Lymphoma[ICD-11: 2A80-2A86]O14757CHEK1
    T62449DI0321Ovarian cancer[ICD-11: 2C73]O14757CHEK1
    T62449DI0326Pancreatic cancer[ICD-11: 2C10]O14757CHEK1
    T62449DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14757CHEK1
    T63505DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00519ABL1
    T63505DI0220Ischemia[ICD-11: 8B10-8B11]P00519ABL1
    T63505DI0250Mature B-cell lymphoma[ICD-11: 2A85]P00519ABL1
    T63505DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00519ABL1
    T69991DI0321Ovarian cancer[ICD-11: 2C73]P30291WEE1
    T69991DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P30291WEE1
    T69991DI0429Uterine ligament/parametrium/uterine adnexa neoplasm[ICD-11: 2C72]P30291WEE1
    T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
    T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
    T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
    T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
    T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
    T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
    T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
    T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
    T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
    T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
    T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
    T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
    T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
    T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
    T13176DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q9NZJ5EIF2AK3
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    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
    T12119DI0051Bipolar disorder[ICD-11: 6A60]Q15858SCN9A
    T12119DI0087Chronic pain[ICD-11: MG30]Q15858SCN9A
    T12119DI0140Extremities vasodilatation[ICD-11: EG00]Q15858SCN9A
    T12119DI0163General pain disorder[ICD-11: 8E43]Q15858SCN9A
    T12119DI0320Osteoarthritis[ICD-11: FA00-FA05]Q15858SCN9A
    T12119DI0324Pain[ICD-11: MG30-MG3Z]Q15858SCN9A
    T12119DI0358Radiculopathy[ICD-11: 8B93]Q15858SCN9A
    T12119DI0415Trigeminal nerve disorder[ICD-11: 8B82]Q15858SCN9A
    T67849DI0151Follicular lymphoma[ICD-11: 2A80]O00329PIK3CD
    T67849DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]O00329PIK3CD
    T67849DI0249Mature B-cell leukaemia[ICD-11: 2A82]O00329PIK3CD
    T67849DI0250Mature B-cell lymphoma[ICD-11: 2A85]O00329PIK3CD
    T67849DI0395Stomach cancer[ICD-11: 2B72]O00329PIK3CD
    T98269DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P29466CASP1
    T98269DI0146Fibrosis[ICD-11: GA14-GC01]P29466CASP1
    T98269DI0366Rheumatoid arthritis[ICD-11: FA20]P29466CASP1
    T98269DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P29466CASP1
    T58970DI0036Arteries/arterioles disorder[ICD-11: BD52]P28482MAPK1
    T58970DI0252Melanoma[ICD-11: 2C30]P28482MAPK1
    T58970DI0326Pancreatic cancer[ICD-11: 2C10]P28482MAPK1
    T58970DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28482MAPK1
    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
    T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
    T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
    T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
    T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
    T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
    T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
    T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
    T45262DI0394Staphylococcal/streptococcal disease[ICD-11: 1B5Y]P34998CRHR1
    T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
    T15700DI0120Diabetes mellitus[ICD-11: 5A10]Q9UQ81MCH5
    T15700DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQ81MCH5
    T95913DI0151Follicular lymphoma[ICD-11: 2A80]P48736PIK3CG
    T95913DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P48736PIK3CG
    T95913DI0249Mature B-cell leukaemia[ICD-11: 2A82]P48736PIK3CG
    T18299DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UQM7CAMK2A
    T58589DI0320Osteoarthritis[ICD-11: FA00-FA05]P46663BDKRB1
    T58589DI0365Retinopathy[ICD-11: 9B71]P46663BDKRB1
    T58589DI0366Rheumatoid arthritis[ICD-11: FA20]P46663BDKRB1
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T10265DI0037Asthma[ICD-11: CA23]Q07343PDE4B
    T10265DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q07343PDE4B
    T10265DI0265Mild neurocognitive disorder[ICD-11: 6D71]Q07343PDE4B
    T11241DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q99500S1PR3

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