Gravacridonetriol glucoside



Compound IDCDAMM00624
Common nameGravacridonetriol glucoside
IUPAC name2-[1,2-dihydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-5-hydroxy-11-methyl-1,2-dihydrofuro[2,3-c]acridin-6-one
Molecular formulaC25H29NO11

Experimental data

Retention time13.05
Adduct[M+H]+
Actual mz520.174
Theoretical mz520.181
Error13.8
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7827

Identifiers and class information

Inchi keyBFVREXFWNFMMSF-UHFFFAOYNA-N
SmilesO=C1C=2C=CC=CC2N(C=3C1=C(O)C=C4OC(CC43)C(O)(CO)COC5OC(CO)C(O)C(O)C5O)C
SuperclassLipids and lipid-like molecules
ClassGlycerolipids

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)2
    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)13
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)519.504
    Computed dipole moment(dipole)4.767
    Total solvent accessible surface area (SASA)788.08
    Hydrophobic component of SASA (FOSA)256.085
    Hydrophilic component of SASA (FISA)311.755
    Pie component of the SASA (PISA)220.24
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1455.51
    Number of hydrogen bond donors (donorHB)6
    Number of hydrogen bond acceptors (accptHB)15.65
    Free energy of solvation of dipole (dip^2/V)0.0156114
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0486429
    Globularity descriptor (glob)0.788144
    Predicted polarizability in cubic angstroms (QPpolrz)45.852
    Predicted hexadecane/gas partition coefficient (QPlogPC16)16.943
    Predicted octanol/gas partition coefficient (QPlogPoct)33.125
    Predicted water/gas partition coefficient (QPlogPw)26.569
    Predicted octanol/water partition coefficient (QPlogPo/w)-0.372
    Predicted aqueous solubility (QPlogS)-3.293
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.346
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.01
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)10.953
    Predicted brain/blood partition coefficient (QPlogBB)-3.566
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3.761
    Predicted skin permeability, log Kp (QPlogKp)-5.241
    PM3 calculated ionization potential (IP(ev))8.291
    PM3 calculated electron affinity (EA(eV))0.405
    Number of likely metabolic reactions (#metab)11
    Prediction of binding to human serum albumin (QPlogKhsa)-0.894
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)4.497
    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)199.304
    Number of nitrogen and oxygen atoms (#NandO)12
    Number of violations of Lipinski’s rule of five (RuleOfFive)3
    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
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P11387TOP1DNA topoisomerase IT09826SwissTargetPrediction and SEA
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P01375TNFTNF-alphaT20178SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
    O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
    P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction and SEA
    O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
    P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
    P17931LGALS3Galectin-3T72038SwissTargetPrediction
    P14679TYRTyrosinaseT97035SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P05231IL6Interleukin-6T32578SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    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
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
    T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
    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
    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
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
    T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
    T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
    T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
    T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
    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
    T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
    T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
    T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
    T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
    T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
    T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
    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
    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
    T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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