Acutoside A



Compound IDCDAMM01880
Common nameAcutoside A
IUPAC name10-[4,5-dihydroxy-6-(hydroxymethyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Molecular formulaC42H68O13

Experimental data

Retention time14.86
Adduct[M+H]+
Actual mz781.47
Theoretical mz781.473
Error3.94
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2078

Identifiers and class information

Inchi keyLEQCLUFJRGKLOA-UHFFFAOYNA-N
SmilesO=C(O)C12CCC(C)(C)CC2C3=CCC4C5(C)CCC(OC6OC(CO)C(O)C(O)C6OC7OC(CO)C(O)C(O)C7O)C(C)(C)C5CCC4(C)C3(C)CC1
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Plant source

  • Curcuma longa L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)8
    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)14
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)780.991
    Computed dipole moment(dipole)7.442
    Total solvent accessible surface area (SASA)930.727
    Hydrophobic component of SASA (FOSA)689.6
    Hydrophilic component of SASA (FISA)223.018
    Pie component of the SASA (PISA)18.109
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)2089.54
    Number of hydrogen bond donors (donorHB)8
    Number of hydrogen bond acceptors (accptHB)20.7
    Free energy of solvation of dipole (dip^2/V)0.0265074
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0629061
    Globularity descriptor (glob)0.849264
    Predicted polarizability in cubic angstroms (QPpolrz)68.653
    Predicted hexadecane/gas partition coefficient (QPlogPC16)20.197
    Predicted octanol/gas partition coefficient (QPlogPoct)46.75
    Predicted water/gas partition coefficient (QPlogPw)32.617
    Predicted octanol/water partition coefficient (QPlogPo/w)2.231
    Predicted aqueous solubility (QPlogS)-3.812
    Conformation-independent predicted aqueous solubility (CIQPlogS)-6.343
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.25
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)19.258
    Predicted brain/blood partition coefficient (QPlogBB)-2.342
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)8.804
    Predicted skin permeability, log Kp (QPlogKp)-4.222
    PM3 calculated ionization potential (IP(ev))9.86
    PM3 calculated electron affinity (EA(eV))-0.568
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)-0.359
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)24.126
    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)205.575
    Number of nitrogen and oxygen atoms (#NandO)13
    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
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P29350PTPN6Protein-tyrosine phosphatase 1CT98264SEA
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
    P17706PTPN2T-cell protein-tyrosine phosphataseT49156SEA
    Q8TDU6GPBAR1G-protein coupled bile acid receptor 1T86273SEA
    P06746POLBDNA polymerase beta (by homology)T06958SEA
    P13726F3Coagulation factor VII/tissue factorT72702SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P60568IL2Interleukin-2T61698SEA
    P17931LGALS3Galectin-3T72038SEA
    P16885PLCG2Phospholipase C-gamma-2T93922SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    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
    T49156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P17706PTPN2
    T86273DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q8TDU6GPBAR1
    T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
    T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
    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
    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

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