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Showing NP-Card for 3-hydroxy-4-methoxy-4-oxobutanoic acid (NP0261397)

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Record Information
Version1.0
Created at2022-09-08 03:50:00 UTC
Updated at2022-09-08 03:50:00 UTC
NP-MRD IDNP0261397
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-hydroxy-4-methoxy-4-oxobutanoic acid
Description3-Hydroxy-4-methoxy-4-oxobutanoic acid belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 3-hydroxy-4-methoxy-4-oxobutanoic acid is found in Agave americana, Myrciaria dubia and Opuntia ficus-indica. 3-Hydroxy-4-methoxy-4-oxobutanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0261397 (3-hydroxy-4-methoxy-4-oxobutanoic acid)


  Mrv1533004171515082D          

 10  9  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   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
    3.9039    1.4289    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
    4.6184    1.8414    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for NP0261397 (3-hydroxy-4-methoxy-4-oxobutanoic acid)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
    3.0993   -0.7610    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8263   -0.1904    0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953    0.0927   -0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3483   -0.1543   -1.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239    0.6923   -0.4704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0439    0.9176   -1.6301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0830   -0.2222    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4437    0.3316    0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311    1.4199    0.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309   -0.3266    1.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107   -0.5088   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700   -1.8527    0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7612   -0.2752    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    1.6779    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035    1.7447   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -1.1998   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -0.3542    1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9207   -1.0316    1.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  1
  6 15  1  0
  7 16  1  0
  7 17  1  0
 10 18  1  0
M  END
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3D SDF for NP0261397 (3-hydroxy-4-methoxy-4-oxobutanoic acid)


  Mrv1533004171515082D          

 10  9  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   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
    3.9039    1.4289    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
    4.6184    1.8414    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261397

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O5/c1-10-5(9)3(6)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)

> <INCHI_KEY>
RTSODCRZYKSCLO-UHFFFAOYSA-N

> <FORMULA>
C5H8O5

> <MOLECULAR_WEIGHT>
148.114

> <EXACT_MASS>
148.037173358

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.05593363325989

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-4-methoxy-4-oxobutanoic acid

> <ALOGPS_LOGP>
-0.84

> <JCHEM_LOGP>
-0.9677473719999998

> <ALOGPS_LOGS>
0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.730532282035806

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.816934934707345

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9167100946655333

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
29.644299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-methoxy-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0261397 (3-hydroxy-4-methoxy-4-oxobutanoic acid)

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PDB for NP0261397 (3-hydroxy-4-methoxy-4-oxobutanoic 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       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.620   2.667   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   10  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    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0261397 (3-hydroxy-4-methoxy-4-oxobutanoic acid)
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SMILES for NP0261397 (3-hydroxy-4-methoxy-4-oxobutanoic acid)
COC(=O)C(O)CC(O)=O
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INCHI for NP0261397 (3-hydroxy-4-methoxy-4-oxobutanoic acid)
InChI=1S/C5H8O5/c1-10-5(9)3(6)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
3-Hydroxy-4-methoxy-4-oxobutanoateGenerator
2-Hydroxysuccinate methyl esterGenerator
Chemical FormulaC5H8O5
Average Mass148.1140 Da
Monoisotopic Mass148.03717 Da
IUPAC Name3-hydroxy-4-methoxy-4-oxobutanoic acid
Traditional Name3-hydroxy-4-methoxy-4-oxobutanoic acid
CAS Registry NumberNot Available
SMILES
COC(=O)C(O)CC(O)=O
InChI Identifier
InChI=1S/C5H8O5/c1-10-5(9)3(6)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)
InChI KeyRTSODCRZYKSCLO-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
Agave americanaLOTUS Database
Myrciaria dubiaLOTUS Database
Opuntia ficus-indicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassHydroxy acids and derivatives  
Sub ClassBeta hydroxy acids and derivatives  
Direct ParentBeta hydroxy acids and derivatives  
Alternative Parents
Substituents
  • Beta-hydroxy acid
    • 

  • Fatty acid ester
    • 

  • Short-chain hydroxy acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Fatty acyl
    • 

  • Methyl ester
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • 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-0.84ALOGPS
logP-0.97ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity29.64 m³·mol⁻¹ChemAxon
Polarizability13.06 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 Compound12100555  
PDB IDNot Available
ChEBI ID143541  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]