Showing NP-Card for 2-Isopropylmalic acid (NP0000126)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:13:02 UTC
NP-MRD IDNP0000126
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Isopropylmalic acid
Description2-Isopropylmalic acid is an alpha-hydroxy organic acid regularly occurring in urine of healthy individuals (PMIDs 2338430, 544608), and in hemofiltrates. (PMID 7251751 ) 2-Isopropylmalic acid is elevated during fasting and diabetic ketoacidosis. (PMID 1591279 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000126 (2-Isopropylmalic acid)

 
  Mrv1652309042000012D          
 
 12 11  0  0  1  0            999 V2000
   10.5611   -8.7683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2737   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5611   -9.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9900   -8.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1323   -8.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -7.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8864  -10.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2775  -10.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0089   -9.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7026   -8.3551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1931   -9.1702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  1 12  1  6  0  0  0
M  END
Download

3D MOL for NP0000126 (2-Isopropylmalic acid)

HMDB0000402
     RDKit          3D
2-Isopropylmalic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -2.1116   -0.6181    0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6157   -0.6108   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0111   -1.7475    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246    0.7427    0.0893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1741    1.0130    1.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908    0.9135   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3712   -0.0008    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352    0.1678    1.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -1.0860   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    1.7304   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8524    1.6725   -1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    2.6939   -0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1762   -0.4263    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4490   -1.6771   -0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849    0.0525   -0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909   -0.7560   -1.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643   -2.4239   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -1.4876    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7918   -2.4267    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639    0.1722    1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7081    1.9577   -0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070    0.9540   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -2.0456   -0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2637    3.2361    0.7796 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  1
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

3D SDF for NP0000126 (2-Isopropylmalic acid)

 
  Mrv1652309042000012D          
 
 12 11  0  0  1  0            999 V2000
   10.5611   -8.7683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2737   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5611   -9.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9900   -8.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1323   -8.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -7.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8864  -10.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2775  -10.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0089   -9.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7026   -8.3551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1931   -9.1702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  1 12  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000126

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@](O)(CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1

> <INCHI_KEY>
BITYXLXUCSKTJS-ZETCQYMHSA-N

> <FORMULA>
C7H12O5

> <MOLECULAR_WEIGHT>
176.1672

> <EXACT_MASS>
176.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.372264381734986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
0.20661967933333347

> <ALOGPS_LOGS>
0.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.566000838313116

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.629835264652623

> <JCHEM_PKA_STRONGEST_BASIC>
-4.140578200901909

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
38.5841

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropyl-malic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000126 (2-Isopropylmalic acid)

HMDB0000402
     RDKit          3D
2-Isopropylmalic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -2.1116   -0.6181    0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6157   -0.6108   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0111   -1.7475    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246    0.7427    0.0893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1741    1.0130    1.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908    0.9135   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3712   -0.0008    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352    0.1678    1.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -1.0860   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    1.7304   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8524    1.6725   -1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    2.6939   -0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1762   -0.4263    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4490   -1.6771   -0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849    0.0525   -0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909   -0.7560   -1.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643   -2.4239   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -1.4876    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7918   -2.4267    1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639    0.1722    1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7081    1.9577   -0.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070    0.9540   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -2.0456   -0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2637    3.2361    0.7796 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  1
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

PDB for NP0000126 (2-Isopropylmalic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      19.714 -16.367   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.044 -15.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.384 -15.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.714 -17.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.381 -16.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.047 -16.367   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.384 -14.061   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.455 -18.674   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.051 -18.674   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.417 -18.044   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.712 -15.596   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      20.894 -17.118   0.000  0.00  0.00           O+0
CONECT    1    2    3    4   12                                             
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
Download

3D PDB for NP0000126 (2-Isopropylmalic acid)

COMPND    HMDB0000402
HETATM    1  C1  UNL     1      -2.112  -0.618   0.142  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.616  -0.611  -0.213  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.011  -1.748   0.539  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.025   0.743   0.089  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.174   1.013   1.449  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.391   0.913  -0.378  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.371  -0.001   0.184  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.835   0.168   1.342  1.00  0.00           O  
HETATM    9  O3  UNL     1       2.829  -1.086  -0.528  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.838   1.730  -0.654  1.00  0.00           C  
HETATM   11  O4  UNL     1      -0.852   1.672  -1.897  1.00  0.00           O  
HETATM   12  O5  UNL     1      -1.565   2.694  -0.006  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.176  -0.426   1.216  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.449  -1.677  -0.042  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.685   0.052  -0.499  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.591  -0.756  -1.321  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.464  -2.424  -0.231  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.666  -1.488   1.347  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.792  -2.427   1.001  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.364   0.172   1.932  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.708   1.958  -0.079  1.00  0.00           H  
HETATM   22  H10 UNL     1       1.407   0.954  -1.494  1.00  0.00           H  
HETATM   23  H11 UNL     1       2.842  -2.046  -0.182  1.00  0.00           H  
HETATM   24  H12 UNL     1      -1.264   3.236   0.780  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5    6   10
CONECT    5   20
CONECT    6    7   21   22
CONECT    7    8    8    9
CONECT    9   23
CONECT   10   11   11   12
CONECT   12   24
END
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SMILES for NP0000126 (2-Isopropylmalic acid)

CC(C)[C@@](O)(CC(O)=O)C(O)=O
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INCHI for NP0000126 (2-Isopropylmalic acid)

InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1
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View in JSmol
Synonyms
Chemical FormulaC7H12O5
Average Mass176.1672 Da
Monoisotopic Mass176.06847 Da
IUPAC Name(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
Traditional Name2-isopropyl-malic acid
CAS Registry Number3237-44-3
SMILES
CC(C)[C@@](O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1
InChI KeyBITYXLXUCSKTJS-ZETCQYMHSA-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 Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility181 g/LALOGPS
logP-0.29ALOGPS
logP0.21ChemAxon
logS0.01ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.58 m³·mol⁻¹ChemAxon
Polarizability16.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000402
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030115
KNApSAcK IDC00019690
Chemspider ID4444155
KEGG Compound IDC02504
BioCyc ID3-CARBOXY-3-HYDROXY-ISOCAPROATE
BiGG IDNot Available
Wikipedia LinkIsopropylmalic acid
METLIN ID339
PubChem Compound5280523
PDB IDNot Available
ChEBI ID35128
Good Scents IDNot Available
References
General References