Lucuminic acid



Compound IDCDAMM00516
Common nameLucuminic acid
IUPAC name2-phenyl-2-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxan-2-yl]oxyacetic acid
Molecular formulaC19H26O12

Experimental data

Retention time13.46
Adduct[M+H]+
Actual mz447.149
Theoretical mz447.149
Error0.05
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.223

Identifiers and class information

Inchi keyDUZCTLMSDUOYAW-UHFFFAOYNA-N
SmilesO=C(O)C(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C=3C=CC=CC3
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)3
    Number of non-conjugated amine groups (#amine)0
    Number of amidine and guanidine groups (#amidine)0
    Number of carboxylic acid groups (#acid)1
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)13
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)446.407
    Computed dipole moment(dipole)6.389
    Total solvent accessible surface area (SASA)649.361
    Hydrophobic component of SASA (FOSA)170.188
    Hydrophilic component of SASA (FISA)294.59
    Pie component of the SASA (PISA)184.583
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1224.07
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)19
    Free energy of solvation of dipole (dip^2/V)0.0333499
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0774134
    Globularity descriptor (glob)0.852214
    Predicted polarizability in cubic angstroms (QPpolrz)36.249
    Predicted hexadecane/gas partition coefficient (QPlogPC16)14.56
    Predicted octanol/gas partition coefficient (QPlogPoct)33.315
    Predicted water/gas partition coefficient (QPlogPw)30.64
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.944
    Predicted aqueous solubility (QPlogS)-1.385
    Conformation-independent predicted aqueous solubility (CIQPlogS)-1.492
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.996
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4.036
    Predicted brain/blood partition coefficient (QPlogBB)-2.924
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.626
    Predicted skin permeability, log Kp (QPlogKp)-5.05
    PM3 calculated ionization potential (IP(ev))9.889
    PM3 calculated electron affinity (EA(eV))0.086
    Number of likely metabolic reactions (#metab)8
    Prediction of binding to human serum albumin (QPlogKhsa)-1.559
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0.488
    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)207.601
    Number of nitrogen and oxygen atoms (#NandO)12
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    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
    P05121SERPINE1Plasminogen activator inhibitor-1T15556SwissTargetPrediction
    P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
    P25105PTAFRPlatelet activating factor receptorT87023SwissTargetPrediction
    P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SwissTargetPrediction and SEA
    P05230FGF1Acidic fibroblast growth factorT18639SwissTargetPrediction and SEA
    P09038FGF2Basic fibroblast growth factorT31621SwissTargetPrediction and SEA
    Q9Y251HPSEHeparanaseT47623SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P35346SSTR5Somatostatin receptor 5T64830SwissTargetPrediction
    P30874SSTR2Somatostatin receptor 2T53024SwissTargetPrediction
    P31391SSTR4Somatostatin receptor 4T62974SwissTargetPrediction
    P30872SSTR1Somatostatin receptor 1T16633SwissTargetPrediction
    P32745SSTR3Somatostatin receptor 3T13644SwissTargetPrediction
    P16109SELPP-selectinT10965SwissTargetPrediction and SEA
    Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
    P17931LGALS3Galectin-3T72038SwissTargetPrediction and SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    Q15077P2RY6Pyrimidinergic receptor P2Y6T90782SEA
    P09382LGALS1Galectin-1T09544SEA
    P11717IGF2RInsulin-like growth factor II receptorT59550SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T15556DI0037Asthma[ICD-11: CA23]P05121SERPINE1
    T15556DI0405Thrombosis[ICD-11: DB61-GB90]P05121SERPINE1
    T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
    T87023DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P25105PTAFR
    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
    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
    T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
    T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
    T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
    T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
    T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
    T64830DI0108Cushing syndrome[ICD-11: 5A70]P35346SSTR5
    T53024DI0108Cushing syndrome[ICD-11: 5A70]P30874SSTR2
    T53024DI0122Diagnostic imaging[ICD-11: N.A.]P30874SSTR2
    T53024DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30874SSTR2
    T62974DI0087Chronic pain[ICD-11: MG30]P31391SSTR4
    T62974DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P31391SSTR4
    T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
    T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
    T13644DI0108Cushing syndrome[ICD-11: 5A70]P32745SSTR3
    T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
    T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
    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
    T90782DI0025Alzheimer disease[ICD-11: 8A20]Q15077P2RY6
    T59550DI0146Fibrosis[ICD-11: GA14-GC01]P11717IGF2R
    T59550DI0368Sarcoidosis[ICD-11: 4B20]P11717IGF2R

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