Medicocarpin



Compound IDCDAMM00520
Common nameMedicocarpin
IUPAC name2-(hydroxymethyl)-6-[(9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-yl)oxy]oxane-3,4,5-triol
Molecular formulaC22H24O9

Experimental data

Retention time7.85
Adduct[M+K]+
Actual mz471.111
Theoretical mz471.105
Error12.19
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.8203

Identifiers and class information

Inchi keyPVEMGMOWXQUWRD-UHFFFAOYNA-N
SmilesOCC1OC(OC2=CC=C3C(OCC4C5=CC=C(OC)C=C5OC34)=C2)C(O)C(O)C1O
SuperclassPhenylpropanoids and polyketides
ClassIsoflavonoids

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)8
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)432.426
    Computed dipole moment(dipole)2.145
    Total solvent accessible surface area (SASA)662.621
    Hydrophobic component of SASA (FOSA)296.82
    Hydrophilic component of SASA (FISA)160.826
    Pie component of the SASA (PISA)204.975
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1219.87
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)11.5
    Free energy of solvation of dipole (dip^2/V)0.003772
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0347106
    Globularity descriptor (glob)0.833251
    Predicted polarizability in cubic angstroms (QPpolrz)39.486
    Predicted hexadecane/gas partition coefficient (QPlogPC16)13.035
    Predicted octanol/gas partition coefficient (QPlogPoct)25.094
    Predicted water/gas partition coefficient (QPlogPw)19.223
    Predicted octanol/water partition coefficient (QPlogPo/w)1.12
    Predicted aqueous solubility (QPlogS)-3.313
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.263
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.208
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)295.658
    Predicted brain/blood partition coefficient (QPlogBB)-1.463
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)132.537
    Predicted skin permeability, log Kp (QPlogKp)-2.993
    PM3 calculated ionization potential (IP(ev))8.953
    PM3 calculated electron affinity (EA(eV))-0.166
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-0.49
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)77.727
    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)125.014
    Number of nitrogen and oxygen atoms (#NandO)9
    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
    P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SEA
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    P43235CTSKCathepsin KT11388SwissTargetPrediction
    Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
    P00519ABL1Tyrosine-protein kinase ABLT63505SwissTargetPrediction
    P07711CTSLCathepsin LT98691SwissTargetPrediction
    Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
    P25774CTSSCathepsin ST68290SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction
    P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
    O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
    Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
    P42574CASP3Caspase-3T57943SwissTargetPrediction
    P14151SELLLeukocyte adhesion molecule-1T60526SEA
    O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
    P60568IL2Interleukin-2T61698SEA
    P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SwissTargetPrediction
    Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
    P60842EIF4A1Eukaryotic initiation factor 4A-IT86805SwissTargetPrediction
    P16234PDGFRAPlatelet-derived growth factor receptorT53524SwissTargetPrediction
    P11166SLC2A1Glucose transporter (by homology)T89458SwissTargetPrediction
    P09382LGALS1Galectin-1T09544SEA
    P01111NRASGTPase NRasT35486SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P05231IL6Interleukin-6T32578SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
    T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
    T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
    T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
    T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
    T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
    T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
    T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
    T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
    T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
    T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
    T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
    T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
    T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
    T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
    T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
    T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
    T11388DI0237Low bone mass disorder[ICD-11: FB83]P43235CTSK
    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
    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
    T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
    T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
    T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
    T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
    T68290DI0042Autoimmune disease[ICD-11: 4A40-4A45]P25774CTSS
    T68290DI0092Coeliac disease[ICD-11: DA95]P25774CTSS
    T68290DI0107Crohn disease[ICD-11: DD70]P25774CTSS
    T68290DI0120Diabetes mellitus[ICD-11: 5A10]P25774CTSS
    T68290DI0163General pain disorder[ICD-11: 8E43]P25774CTSS
    T68290DI0324Pain[ICD-11: MG30-MG3Z]P25774CTSS
    T68290DI0382Sjogren syndrome[ICD-11: 4A43]P25774CTSS
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
    T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
    T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
    T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
    T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
    T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
    T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
    T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
    T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
    T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
    T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
    T60526DI0037Asthma[ICD-11: CA23]P14151SELL
    T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
    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
    T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
    T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
    T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
    T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
    T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
    T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
    T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
    T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T86805DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P60842EIF4A1
    T53524DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P16234PDGFRA
    T53524DI0225Kaposi sarcoma[ICD-11: 2B57]P16234PDGFRA
    T53524DI0403Thrombocytopenia[ICD-11: 3B64]P16234PDGFRA
    T89458DI0384Skin disease[ICD-11: EA00-EM0Z]P11166SLC2A1
    T35486DI0095Colorectal cancer[ICD-11: 2B91]P01111NRAS
    T35486DI0172Head and neck cancer[ICD-11: 2D42]P01111NRAS
    T35486DI0238Lung cancer[ICD-11: 2C25]P01111NRAS
    T35486DI0326Pancreatic cancer[ICD-11: 2C10]P01111NRAS
    T35486DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P01111NRAS
    T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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