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Showing NP-Card for 2,2-Dimethylsuccinic acid (NP0001223)

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Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2021-06-29 00:47:20 UTC
NP-MRD IDNP0001223
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,2-Dimethylsuccinic acid
Description2,2-Dimethylsuccinic acid is an alpha,omega-dicarboxylic acid that is succinic acid substituted by two methyl groups at positions 2 and 2 respectively. It derives from a succinic acid. 2,2-Dimethylsuccinic acid, also known as 2,2-dimethylbutanedioate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. 2,2-Dimethylsuccinic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001223 (2,2-Dimethylsuccinic acid)


  Mrv1652305261923552D          

 10  9  0  0  0  0            999 V2000
   14.3275   -6.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0582   -5.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7552   -6.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6305   -5.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2936   -6.8468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0921   -4.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3613   -5.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4860   -5.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1829   -6.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5199   -4.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
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3D MOL for NP0001223 (2,2-Dimethylsuccinic acid)

HMDB0002074
     RDKit          3D
2,2-Dimethylsuccinic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.6515   -0.8467   -1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4514   -0.1611    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3839   -0.9059    0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285   -0.2178    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    0.3572   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8605    0.8873   -1.3513 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849    0.3258    0.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9000    1.2457   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802    1.5933    0.8181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772    2.1583   -0.9192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2038   -0.3458   -2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584   -0.8586   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -1.9131   -1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2214   -1.3821    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8052   -0.2206    1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8270   -1.7081    1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952    0.2142    1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -1.3099    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078    0.3298    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362    2.7581   -1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  7 19  1  0
 10 20  1  0
M  END
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3D SDF for NP0001223 (2,2-Dimethylsuccinic acid)


  Mrv1652305261923552D          

 10  9  0  0  0  0            999 V2000
   14.3275   -6.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0582   -5.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7552   -6.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6305   -5.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2936   -6.8468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0921   -4.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3613   -5.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4860   -5.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1829   -6.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5199   -4.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001223

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c1-6(2,5(9)10)3-4(7)8/h3H2,1-2H3,(H,7,8)(H,9,10)

> <INCHI_KEY>
GOHPTLYPQCTZSE-UHFFFAOYSA-N

> <FORMULA>
C6H10O4

> <MOLECULAR_WEIGHT>
146.1412

> <EXACT_MASS>
146.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.751392340489545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-dimethylbutanedioic acid

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
0.700517613

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.711758310111835

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1041071085585825

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
32.6125

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-dimethylsuccinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001223 (2,2-Dimethylsuccinic acid)

HMDB0002074
     RDKit          3D
2,2-Dimethylsuccinic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.6515   -0.8467   -1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4514   -0.1611    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3839   -0.9059    0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285   -0.2178    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    0.3572   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8605    0.8873   -1.3513 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849    0.3258    0.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9000    1.2457   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802    1.5933    0.8181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772    2.1583   -0.9192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2038   -0.3458   -2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584   -0.8586   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -1.9131   -1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2214   -1.3821    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8052   -0.2206    1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8270   -1.7081    1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952    0.2142    1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -1.3099    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078    0.3298    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362    2.7581   -1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  7 19  1  0
 10 20  1  0
M  END
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PDB for NP0001223 (2,2-Dimethylsuccinic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      26.745 -11.242   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.109 -10.527   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.410 -11.352   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      25.444 -10.418   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      26.681 -12.781   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      28.172  -8.989   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.808  -9.703   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.774 -10.637   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      32.075 -11.461   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      30.837  -9.098   0.000  0.00  0.00           O+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3    6    7                                             
CONECT    3    2    8                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    3    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 NP0001223 (2,2-Dimethylsuccinic acid)

COMPND    HMDB0002074
HETATM    1  C1  UNL     1      -0.651  -0.847  -1.289  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.451  -0.161   0.027  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.384  -0.906   0.996  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.929  -0.218   0.570  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.997   0.357  -0.227  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.861   0.887  -1.351  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.285   0.326   0.285  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.900   1.246  -0.010  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.780   1.593   0.818  1.00  0.00           O  
HETATM   10  O4  UNL     1      -0.377   2.158  -0.919  1.00  0.00           O  
HETATM   11  H1  UNL     1      -0.204  -0.346  -2.144  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.758  -0.859  -1.465  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.358  -1.913  -1.186  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.221  -1.382   0.473  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.805  -0.221   1.745  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.827  -1.708   1.538  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.995   0.214   1.594  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.180  -1.310   0.729  1.00  0.00           H  
HETATM   19  H9  UNL     1       3.508   0.330   1.257  1.00  0.00           H  
HETATM   20  H10 UNL     1      -1.036   2.758  -1.440  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4    8
CONECT    3   14   15   16
CONECT    4    5   17   18
CONECT    5    6    6    7
CONECT    7   19
CONECT    8    9    9   10
CONECT   10   20
END
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SMILES for NP0001223 (2,2-Dimethylsuccinic acid)

CC(C)(CC(O)=O)C(O)=O
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INCHI for NP0001223 (2,2-Dimethylsuccinic acid)

InChI=1S/C6H10O4/c1-6(2,5(9)10)3-4(7)8/h3H2,1-2H3,(H,7,8)(H,9,10)
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View in JSmol
Synonyms
ValueSource
2,2-DimethylsuccinateGenerator
2,2,-DimethylsuccinateHMDB
2,2-Dimethyl succinateHMDB
2,2-Dimethyl succinic acidHMDB
2,2-DimethylbutanedioateHMDB
2,2-Dimethylbutanedioic acidHMDB
alpha,alpha-Dimethyl-succinateHMDB
alpha,alpha-Dimethyl-succinic acidHMDB
2,2-Dimethyl-succinateHMDB
2,2-Dimethylsuccinic acidMeSH
Chemical FormulaC6H10O4
Average Mass146.1412 Da
Monoisotopic Mass146.05791 Da
IUPAC Name2,2-dimethylbutanedioic acid
Traditional Name2,2-dimethylsuccinic acid
CAS Registry Number597-43-3
SMILES
CC(C)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O4/c1-6(2,5(9)10)3-4(7)8/h3H2,1-2H3,(H,7,8)(H,9,10)
InChI KeyGOHPTLYPQCTZSE-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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 methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Dicarboxylic acid or derivatives
  • 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 Point140.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility70 mg/mL at 14 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility91.5 g/LALOGPS
logP0.41ALOGPS
logP0.7ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.61 m³·mol⁻¹ChemAxon
Polarizability13.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002074
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022833
KNApSAcK IDNot Available
Chemspider ID11209
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6473
PubChem Compound11701
PDB IDNot Available
ChEBI ID86537
Good Scents IDNot Available
References
General References
  1. Kelley RI: Octenylsuccinic aciduria in children fed protein-hydrolysate formulas containing modified cornstarch. Pediatr Res. 1991 Dec;30(6):564-9. [PubMed:1805153 ]
  2. Giordano G, McMurray WJ, Previs SF, Welch RD, Rinaldo P: Identification of 2-(2'-octenyl) succinic acid in urine. Rapid Commun Mass Spectrom. 1990 May;4(5):170-2. [PubMed:2134344 ]
  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. Authors unspecified: Testicular Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:26389404 ]
  8. Cheng CT, Chan MN, Wilson KR: The role of alkoxy radicals in the heterogeneous reaction of two structural isomers of dimethylsuccinic acid. Phys Chem Chem Phys. 2015 Oct 14;17(38):25309-21. doi: 10.1039/c5cp03791c. [PubMed:26356151 ]
  9. Song M, Marcolli C, Krieger UK, Lienhard DM, Peter T: Morphologies of mixed organic/inorganic/aqueous aerosol droplets. Faraday Discuss. 2013;165:289-316. doi: 10.1039/c3fd00049d. [PubMed:24601008 ]
  10. Seeberger S, Griffin RJ, Hardcastle IR, Golding BT: A new strategy for the synthesis of taurine derivatives using the 'safety-catch' principle for the protection of sulfonic acids. Org Biomol Chem. 2007 Jan 7;5(1):132-8. doi: 10.1039/b614333d. Epub 2006 Nov 24. [PubMed:17164917 ]
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