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Showing NP-Card for 2,3,5-trihydroxy-4-methoxyhexanedioic acid (NP0220728)

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Record Information
Version1.0
Created at2022-09-05 22:07:10 UTC
Updated at2022-09-05 22:07:10 UTC
NP-MRD IDNP0220728
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,3,5-trihydroxy-4-methoxyhexanedioic acid
Description2,3,5-Trihydroxy-4-methoxyhexanedioic acid belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. 2,3,5-trihydroxy-4-methoxyhexanedioic acid is found in Pycnandra acuminata. 2,3,5-Trihydroxy-4-methoxyhexanedioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0220728 (2,3,5-trihydroxy-4-methoxyhexanedioic acid)


  Mrv1533004171512162D          

 15 14  0  0  0  0            999 V2000
    4.6184    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
Download

3D MOL for NP0220728 (2,3,5-trihydroxy-4-methoxyhexanedioic acid)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
   -1.9541    1.9248   -0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796    1.4687    0.4127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319    0.4092    0.0960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7696   -0.7733    0.9181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6954   -0.4828    2.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1834   -1.0523    0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581   -0.9276    1.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -1.4567   -0.6586 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841    0.8364    0.2944 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3062    1.9152   -0.5636 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1515   -0.1556    0.1054 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0729   -1.2768    0.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3911   -0.5891   -1.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5212    0.2458   -2.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -1.9333   -1.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3940    2.3004   -1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5602    2.7993   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092    1.2196   -1.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5057    0.1631   -0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1635   -1.6666    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -0.2652    2.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6669   -2.4173   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    1.2573    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128    1.7310   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150    0.3594    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0270   -1.0658    1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -2.5677   -1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 15  1  0
 13 14  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  8  1  0
  6  7  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  6
  9 23  1  1
 10 24  1  0
 11 25  1  1
 12 26  1  0
 15 27  1  0
  4 20  1  1
  5 21  1  0
  8 22  1  0
M  END
Download

3D SDF for NP0220728 (2,3,5-trihydroxy-4-methoxyhexanedioic acid)


  Mrv1533004171512162D          

 15 14  0  0  0  0            999 V2000
    4.6184    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C(O)C(O)C(O)=O)C(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O8/c1-15-5(4(10)7(13)14)2(8)3(9)6(11)12/h2-5,8-10H,1H3,(H,11,12)(H,13,14)

> <INCHI_KEY>
MDGDZMIEJCCPTI-UHFFFAOYSA-N

> <FORMULA>
C7H12O8

> <MOLECULAR_WEIGHT>
224.165

> <EXACT_MASS>
224.053217346

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.926071286316617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,5-trihydroxy-4-methoxyhexanedioic acid

> <ALOGPS_LOGP>
-1.33

> <JCHEM_LOGP>
-2.446343269

> <ALOGPS_LOGS>
-0.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6614204545626454

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9547311314106923

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7346121184946677

> <JCHEM_POLAR_SURFACE_AREA>
144.51999999999998

> <JCHEM_REFRACTIVITY>
42.8896

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,5-trihydroxy-4-methoxyhexanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0220728 (2,3,5-trihydroxy-4-methoxyhexanedioic acid)

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PDB for NP0220728 (2,3,5-trihydroxy-4-methoxyhexanedioic acid)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       8.621   0.357   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.953   2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.286   4.977   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

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3D PDB for NP0220728 (2,3,5-trihydroxy-4-methoxyhexanedioic acid)
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SMILES for NP0220728 (2,3,5-trihydroxy-4-methoxyhexanedioic acid)
COC(C(O)C(O)C(O)=O)C(O)C(O)=O
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INCHI for NP0220728 (2,3,5-trihydroxy-4-methoxyhexanedioic acid)
InChI=1S/C7H12O8/c1-15-5(4(10)7(13)14)2(8)3(9)6(11)12/h2-5,8-10H,1H3,(H,11,12)(H,13,14)
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View in JSmol
Synonyms
ValueSource
2,3,5-Trihydroxy-4-methoxyhexanedioateGenerator
Chemical FormulaC7H12O8
Average Mass224.1650 Da
Monoisotopic Mass224.05322 Da
IUPAC Name2,3,5-trihydroxy-4-methoxyhexanedioic acid
Traditional Name2,3,5-trihydroxy-4-methoxyhexanedioic acid
CAS Registry NumberNot Available
SMILES
COC(C(O)C(O)C(O)=O)C(O)C(O)=O
InChI Identifier
InChI=1S/C7H12O8/c1-15-5(4(10)7(13)14)2(8)3(9)6(11)12/h2-5,8-10H,1H3,(H,11,12)(H,13,14)
InChI KeyMDGDZMIEJCCPTI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pycnandra acuminataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentGlucuronic acid derivatives  
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
    • 

  • Medium-chain hydroxy acid
    • 

  • Medium-chain fatty acid
    • 

  • Beta-hydroxy acid
    • 

  • Hydroxy fatty acid
    • 

  • Alpha-hydroxy acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Monosaccharide
    • 

  • Hydroxy acid
    • 

  • Secondary alcohol
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Polyol
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-2.4ChemAxon
logS-0.5ALOGPS
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.89 m³·mol⁻¹ChemAxon
Polarizability18.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85860655  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]