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Showing NP-Card for Monomethyl glutaric acid (NP0000866)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:30 UTC
NP-MRD IDNP0000866
Secondary Accession NumbersNone
Natural Product Identification
Common NameMonomethyl glutaric acid
DescriptionMonomethyl glutaric acid, also known as 4-(methoxycarbonyl)butyrate or 2-methyleneglutarate, belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000866 (Monomethyl glutaric acid)

Monomethyl glutarate.mol
  Mrv1652305271900222D          

 10  9  0  0  0  0            999 V2000
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7145    0.0000 C   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
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
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3D MOL for NP0000866 (Monomethyl glutaric acid)

HMDB0000858
     RDKit          3D
Monomethyl glutaric acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.9041    0.7443   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    0.2809   -0.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680   -1.0221    0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -1.8165    0.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454   -1.5482    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0688   -0.5610    0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -0.0028   -0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4211    0.9598   -0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842    0.4892   -0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945    2.3300   -0.6463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210    0.9346   -1.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2035    1.6550    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6522   -0.0324   -0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459   -1.8305    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -2.5019    0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182    0.2700    1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9816   -1.0363    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236    0.5440   -1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442   -0.8196   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6057    2.9634    0.0472 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
M  END
Download

3D SDF for NP0000866 (Monomethyl glutaric acid)

Monomethyl glutarate.mol
  Mrv1652305271900222D          

 10  9  0  0  0  0            999 V2000
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7145    0.0000 C   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
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000866

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c1-10-6(9)4-2-3-5(7)8/h2-4H2,1H3,(H,7,8)

> <INCHI_KEY>
IBMRTYCHDPMBFN-UHFFFAOYSA-N

> <FORMULA>
C6H10O4

> <MOLECULAR_WEIGHT>
146.1412

> <EXACT_MASS>
146.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.313992553637142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methoxy-5-oxopentanoic acid

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.19197975366666636

> <ALOGPS_LOGS>
-0.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.218306175572683

> <JCHEM_PKA_STRONGEST_BASIC>
-7.024135860366669

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
32.9071

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glutaric acid monomethyl ester

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000866 (Monomethyl glutaric acid)

HMDB0000858
     RDKit          3D
Monomethyl glutaric acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.9041    0.7443   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    0.2809   -0.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680   -1.0221    0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -1.8165    0.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454   -1.5482    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0688   -0.5610    0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -0.0028   -0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4211    0.9598   -0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842    0.4892   -0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945    2.3300   -0.6463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210    0.9346   -1.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2035    1.6550    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6522   -0.0324   -0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459   -1.8305    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -2.5019    0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182    0.2700    1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9816   -1.0363    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236    0.5440   -1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442   -0.8196   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6057    2.9634    0.0472 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
M  END
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PDB for NP0000866 (Monomethyl glutaric acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Monomethyl glutarate.mol                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.770   1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    8    9                                                  
CONECT    6    1                                                            
CONECT    7    1   10                                                       
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0000866 (Monomethyl glutaric acid)

COMPND    HMDB0000858
HETATM    1  C1  UNL     1      -2.904   0.744  -0.419  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.624   0.281  -0.042  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.368  -1.022   0.341  1.00  0.00           C  
HETATM    4  O2  UNL     1      -2.339  -1.816   0.348  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.045  -1.548   0.743  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.069  -0.561   0.678  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.295  -0.003  -0.714  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.421   0.960  -0.636  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.584   0.489  -0.554  1.00  0.00           O  
HETATM   10  O4  UNL     1       2.294   2.330  -0.646  1.00  0.00           O  
HETATM   11  H1  UNL     1      -2.921   0.935  -1.520  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.203   1.655   0.153  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.652  -0.032  -0.158  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.146  -1.830   1.830  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.167  -2.502   0.219  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.818   0.270   1.374  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.982  -1.036   1.044  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.424   0.544  -1.114  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.544  -0.820  -1.433  1.00  0.00           H  
HETATM   20  H10 UNL     1       2.606   2.963   0.047  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   14   15
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
END
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SMILES for NP0000866 (Monomethyl glutaric acid)

COC(=O)CCCC(O)=O
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INCHI for NP0000866 (Monomethyl glutaric acid)

InChI=1S/C6H10O4/c1-10-6(9)4-2-3-5(7)8/h2-4H2,1H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
4-(Methoxycarbonyl)butyric acidChEBI
4-Methoxycarbonylbutanoic acidChEBI
Monomethyl glutarateChEBI
4-(Methoxycarbonyl)butyrateGenerator
4-MethoxycarbonylbutanoateGenerator
2-MethyleneglutarateHMDB
4-CarboxybutanoateHMDB
4-Carboxybutanoic acidHMDB
4-Carboxybutanoic acid methyl esterHMDB
5-Methoxy-5-oxopentanoateHMDB
5-Methoxy-5-oxopentanoic acidHMDB
Glutaric acid methyl esterHMDB
Glutaric acid methyl half esterHMDB
Glutaric acid monomethyl esterHMDB
Glutaric acid monomethylesterHMDB
Methyl glutarateHMDB
Methyl glutarate,monoHMDB
Methyl hydrogen glutarateHMDB
mono-Methyl glutarateHMDB
Monomethyl ester OF glutarateHMDB
Monomethyl ester OF glutaric acidHMDB
PentanedioateHMDB
Pentanedioic acidHMDB
Pentanedioic acid monomethyl esterHMDB
Chemical FormulaC6H10O4
Average Mass146.1412 Da
Monoisotopic Mass146.05791 Da
IUPAC Name5-methoxy-5-oxopentanoic acid
Traditional Nameglutaric acid monomethyl ester
CAS Registry Number1501-27-5
SMILES
COC(=O)CCCC(O)=O
InChI Identifier
InChI=1S/C6H10O4/c1-10-6(9)4-2-3-5(7)8/h2-4H2,1H3,(H,7,8)
InChI KeyIBMRTYCHDPMBFN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid methyl esters
Alternative Parents
Substituents
  • Fatty acid methyl ester
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility57.6 g/LALOGPS
logP0.19ALOGPS
logP0.19ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity32.91 m³·mol⁻¹ChemAxon
Polarizability14.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000858
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022284
KNApSAcK IDNot Available
Chemspider ID66550
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5821
PubChem Compound73917
PDB IDNot Available
ChEBI ID86396
Good Scents IDNot Available
References
General References
  1. Hardeman D, Beyer C, Backer ET: Abrupt changes in the concentrations of five prostatic tumor-associated markers in serum after acute myocardial infarction. Clin Chem. 1992 Apr;38(4):605-7. [PubMed:1568341 ]
  2. Bouatra S, Aziat F, Mandal R, Guo AC, Wilson MR, Knox C, Bjorndahl TC, Krishnamurthy R, Saleem F, Liu P, Dame ZT, Poelzer J, Huynh J, Yallou FS, Psychogios N, Dong E, Bogumil R, Roehring C, Wishart DS: The human urine metabolome. PLoS One. 2013 Sep 4;8(9):e73076. doi: 10.1371/journal.pone.0073076. eCollection 2013. [PubMed:24023812 ]
  3. Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Patient Version. 2002. [PubMed:34403226 ]
  4. Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:28876831 ]
  5. Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
  6. Authors unspecified: Adult Soft Tissue Sarcoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389481 ]
  7. Lakey PS, George IJ, Whalley LK, Baeza-Romero MT, Heard DE: Measurements of the HO2 uptake coefficients onto single component organic aerosols. Environ Sci Technol. 2015 Apr 21;49(8):4878-85. doi: 10.1021/acs.est.5b00948. Epub 2015 Apr 9. [PubMed:25811311 ]
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