Lethedoside A



Compound IDCDAMM00615
Common nameLethedoside A
IUPAC name2-(3,4-dimethoxyphenyl)-7-methoxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Molecular formulaC24H26O11

Experimental data

Retention time13.04
Adduct[M+H]+
Actual mz491.159
Theoretical mz491.155
Error8.6
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.6662

Identifiers and class information

Inchi keyVCKHKFVWKVWGMH-WXVMNYTINA-N
SmilesO=C1C=C(OC2=CC(OC)=CC(OC3OC(CO)C(O)C(O)C3O)=C12)C=4C=CC(OC)=C(OC)C4
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

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)10
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)490.463
    Computed dipole moment(dipole)4.138
    Total solvent accessible surface area (SASA)734.403
    Hydrophobic component of SASA (FOSA)383.858
    Hydrophilic component of SASA (FISA)175.147
    Pie component of the SASA (PISA)175.398
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1375.51
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)14
    Free energy of solvation of dipole (dip^2/V)0.0124481
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0381262
    Globularity descriptor (glob)0.814466
    Predicted polarizability in cubic angstroms (QPpolrz)44.148
    Predicted hexadecane/gas partition coefficient (QPlogPC16)14.374
    Predicted octanol/gas partition coefficient (QPlogPoct)28.13
    Predicted water/gas partition coefficient (QPlogPw)21.313
    Predicted octanol/water partition coefficient (QPlogPo/w)0.936
    Predicted aqueous solubility (QPlogS)-3.38
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.566
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.371
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)216.262
    Predicted brain/blood partition coefficient (QPlogBB)-1.799
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)94.524
    Predicted skin permeability, log Kp (QPlogKp)-3.169
    PM3 calculated ionization potential (IP(ev))8.822
    PM3 calculated electron affinity (EA(eV))0.62
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-0.644
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)61.258
    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)155.635
    Number of nitrogen and oxygen atoms (#NandO)11
    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
    P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
    P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P16083NQO2Quinone reductase 2T75498SwissTargetPrediction
    P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
    P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction and SEA
    P08913ADRA2AAlpha-2a adrenergic receptorT11448SwissTargetPrediction
    P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P13726F3Coagulation factor VII/tissue factorT72702SwissTargetPrediction
    P18825ADRA2CAdrenergic receptor alpha-2T01777SwissTargetPrediction
    P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    O14746TERTTelomerase reverse transcriptaseT86052SEA
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P01375TNFTNF-alphaT20178SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction
    P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
    P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SEA
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
    O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
    P14151SELLLeukocyte adhesion molecule-1T60526SEA
    P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SwissTargetPrediction
    P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SwissTargetPrediction
    Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
    P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    P17931LGALS3Galectin-3T72038SEA
    P14679TYRTyrosinaseT97035SEA
    P16234PDGFRAPlatelet-derived growth factor receptorT53524SwissTargetPrediction
    Q9NPH5NOX4NADPH oxidase 4T29741SwissTargetPrediction and SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SwissTargetPrediction and SEA
    P47989XDHXanthine dehydrogenaseT40954SwissTargetPrediction and SEA
    Q8TEK3DOT1LHistone-lysine N-methyltransferase, H3 lysine-79 specificT87686SwissTargetPrediction
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    P09382LGALS1Galectin-1T09544SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    P01111NRASGTPase NRasT35486SwissTargetPrediction
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P05231IL6Interleukin-6T32578SEA
    Q99417MYCBPMYCBP messenger RNAT37298SEA
    P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

    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
    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
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
    T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
    T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
    T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
    T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
    T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
    T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
    T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T11448DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P08913ADRA2A
    T11448DI0317Opioid use disorder[ICD-11: 6C43]P08913ADRA2A
    T11448DI0396Substance abuse[ICD-11: 6C40]P08913ADRA2A
    T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
    T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
    T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
    T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
    T01777DI0166Glaucoma[ICD-11: 9C61]P18825ADRA2C
    T01777DI0190Hypertension[ICD-11: BA00-BA04]P18825ADRA2C
    T01777DI0196Hypotension[ICD-11: BA20-BA21]P18825ADRA2C
    T01777DI0308Obesity[ICD-11: 5B80-5B81]P18825ADRA2C
    T01777DI0310Ocular disease[ICD-11: N.A.]P18825ADRA2C
    T01777DI0396Substance abuse[ICD-11: 6C40]P18825ADRA2C
    T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    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
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
    T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
    T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
    T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
    T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
    T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
    T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
    T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
    T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
    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
    T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
    T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
    T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
    T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
    T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
    T60526DI0037Asthma[ICD-11: CA23]P14151SELL
    T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
    T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
    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
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    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
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T53524DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P16234PDGFRA
    T53524DI0225Kaposi sarcoma[ICD-11: 2B57]P16234PDGFRA
    T53524DI0403Thrombocytopenia[ICD-11: 3B64]P16234PDGFRA
    T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
    T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
    T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
    T87686DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q8TEK3DOT1L
    T87686DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q8TEK3DOT1L
    T87686DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q8TEK3DOT1L
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
    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
    T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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