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Showing NP-Card for Butanedioic acid 1-methyl ester (NP0072405)

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Record Information
Version2.0
Created at2022-04-28 17:45:25 UTC
Updated at2022-04-28 17:45:25 UTC
NP-MRD IDNP0072405
Secondary Accession NumbersNone
Natural Product Identification
Common NameButanedioic acid 1-methyl ester
Description(S)-Methylbutanethioic acid, also known as butanedioic acid 1-methyl ester or succinic acid monomethyl ester, 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. Butanedioic acid 1-methyl ester is found in Oxalis pes-caprae, Panax notoginseng , Pisum sativum and Ranunculus ternatus. Butanedioic acid 1-methyl ester was first documented in 1984 (PMID: 6712257). They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group (S)-Methylbutanethioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 12145163) (PMID: 12369722) (PMID: 1322278) (PMID: 3047128).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0072405 (Butanedioic acid 1-methyl ester)


  Mrv0541 05041407572D          

  9  8  0  0  0  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
M  END
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3D MOL for NP0072405 (Butanedioic acid 1-methyl ester)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
    3.0585    0.7319    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -0.2409   -0.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514   -0.0245   -0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3187    1.1040    0.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -1.0552   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431   -0.5445   -0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0476   -0.1131    0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -0.1652    1.8659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359    0.3793    1.0306 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0249    0.4237   -0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868    0.7790    1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8249    1.7318   -0.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029   -1.9149    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0647   -1.4283   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7282    0.3390   -1.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3218   -1.3503   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4736    1.3484    0.7573 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  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  9 17  1  0
M  END
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3D SDF for NP0072405 (Butanedioic acid 1-methyl ester)


  Mrv0541 05041407572D          

  9  8  0  0  0  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072405

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O4/c1-9-5(8)3-2-4(6)7/h2-3H2,1H3,(H,6,7)

> <INCHI_KEY>
JDRMYOQETPMYQX-UHFFFAOYSA-N

> <FORMULA>
C5H8O4

> <MOLECULAR_WEIGHT>
132.1146

> <EXACT_MASS>
132.042258744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.159632050161846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
-0.2525889113333334

> <ALOGPS_LOGS>
0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.053937854380926

> <JCHEM_PKA_STRONGEST_BASIC>
-7.029745225080873

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
28.3061

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e+02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0072405 (Butanedioic acid 1-methyl ester)

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PDB for NP0072405 (Butanedioic acid 1-methyl ester)
HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6    7                                                  
CONECT    5    3    8    9                                                  
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    1    5                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0072405 (Butanedioic acid 1-methyl ester)
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SMILES for NP0072405 (Butanedioic acid 1-methyl ester)
COC(=O)CCC(O)=O
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INCHI for NP0072405 (Butanedioic acid 1-methyl ester)
InChI=1S/C5H8O4/c1-9-5(8)3-2-4(6)7/h2-3H2,1H3,(H,6,7)
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Synonyms
ValueSource
3-Carbomethoxypropanoic acidChEBI
Butanedioic acid 1-methyl esterChEBI
Butanedioic acid monomethyl esterChEBI
Butanedioic acid, 1-methyl esterChEBI
Methyl hydrogen succinateChEBI
Succinic acid 4-methyl esterChEBI
Succinic acid monomethyl esterChEBI
Succinic acid, monomethyl esterChEBI
3-CarbomethoxypropanoateGenerator
Butanedioate 1-methyl esterGenerator
Butanedioate monomethyl esterGenerator
Butanedioate, 1-methyl esterGenerator
Methyl hydrogen succinic acidGenerator
Succinate 4-methyl esterGenerator
Succinate monomethyl esterGenerator
Succinate, monomethyl esterGenerator
(S)-MethylbutanethioateGenerator
Monomethyl succinic acidHMDB
3H-MethylsuccinateHMDB
DL-MethylsuccinateHMDB
Monomethyl succinate sodium saltHMDB
Methyl succinateHMDB
Monomethyl succinateMeSH
Chemical FormulaC5H8O4
Average Mass132.1146 Da
Monoisotopic Mass132.04226 Da
IUPAC Name4-methoxy-4-oxobutanoic acid
Traditional Name4-methoxy-4-oxobutanoic acid
CAS Registry NumberNot Available
SMILES
COC(=O)CCC(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-9-5(8)3-2-4(6)7/h2-3H2,1H3,(H,6,7)
InChI KeyJDRMYOQETPMYQX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Oxalis pes-capraeLOTUS Database
Panax notoginsengPlant
Pisum sativumLOTUS Database
Ranunculus ternatusLOTUS Database
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.13ALOGPS
logP-0.25ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.31 m³·mol⁻¹ChemAxon
Polarizability12.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061879  
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 Compound77487  
PDB IDNot Available
ChEBI ID75146  
Good Scents IDNot Available
References
General References
  1. Alarcon C, Wicksteed B, Prentki M, Corkey BE, Rhodes CJ: Succinate is a preferential metabolic stimulus-coupling signal for glucose-induced proinsulin biosynthesis translation. Diabetes. 2002 Aug;51(8):2496-504. doi: 10.2337/diabetes.51.8.2496. [PubMed:12145163  ] 
  2. Picton SF, Flatt PR, McClenaghan NH: Differential acute and long term actions of succinic acid monomethyl ester exposure on insulin-secreting BRIN-BD11 cells. Int J Exp Diabetes Res. 2001;2(1):19-27. doi: 10.1155/edr.2001.19. [PubMed:12369722  ] 
  3. Zawalich WS, Zawalich KC: Biochemical mechanisms involved in monomethyl succinate-induced insulin secretion. Endocrinology. 1992 Aug;131(2):649-54. doi: 10.1210/endo.131.2.1322278. [PubMed:1322278  ] 
  4. Fahien LA, MacDonald MJ, Kmiotek EH, Mertz RJ, Fahien CM: Regulation of insulin release by factors that also modify glutamate dehydrogenase. J Biol Chem. 1988 Sep 25;263(27):13610-4. [PubMed:3047128  ] 
  5. Rognstad R: Gluconeogenesis in rat hepatocytes from monomethyl succinate and other esters. Arch Biochem Biophys. 1984 May 1;230(2):605-9. doi: 10.1016/0003-9861(84)90441-7. [PubMed:6712257  ]