Showing metabocard for 2-Isopropylmaleate (MMDBc0049888)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:45:35 UTC
Update Date2022-12-15 22:52:19 UTC
Metabolite IDMMDBc0049888
Metabolite Identification
Common Name2-Isopropylmaleate
Description2-Isopropylmaleic acid 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 one or more methyl groups. However, branches other than methyl groups may be present. 2-Isopropylmaleic acid is a moderately acidic compound (based on its pKa). Isopropylmaleic acid is found in the leucine biosynthesis pathway. It is synthesized from oxoisovalerate by 2-isopropylmalate synthase and converted into isopropyl-3-oxosuccinate by 3-isopropylmalate dehydrogenase. The 2- and 3-isopropyl derivatives of isopropylmaleic acid are interconverted by the enzyme isopropylmalate dehydratase.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005634c28197f8>


  Mrv1652309042000352D          

 11 10  0  0  0  0            999 V2000
   -3.0132    1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276    1.0937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    2.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    2.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    2.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    2.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    0.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00005634c28197f8>

HMDB0012241
     RDKit          3D
Isopropylmaleic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -1.8079   -1.3410   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3649    0.0593   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7129    1.0178   -1.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1150    0.0734    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9289    0.8506   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390    1.0206   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    1.8649   -0.9791 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629    0.3834    0.6475 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -0.8123    1.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -1.5660    1.9044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8078   -0.9817    1.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9655   -1.9943   -0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2357   -1.7711    0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692   -1.3375   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569    0.4333    0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    0.8110   -2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    2.0457   -0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8384    0.9483   -1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    1.4836   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0265   -0.0189    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0743   -1.1691    2.7269 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  8 20  1  0
 11 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00005634c28197f8>


  Mrv1652309042000352D          

 11 10  0  0  0  0            999 V2000
   -3.0132    1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276    1.0937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    2.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    2.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    2.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    2.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    0.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049888

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H10O4/c1-4(2)5(7(10)11)3-6(8)9/h3-4H,1-2H3,(H,8,9)(H,10,11)/b5-3-

> <INCHI_KEY>
NJMGRJLQRLFQQX-HYXAFXHYSA-N

> <FORMULA>
C7H10O4

> <MOLECULAR_WEIGHT>
158.1519

> <EXACT_MASS>
158.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.11437754513191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-2-(propan-2-yl)but-2-enedioic acid

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.0862239193333334

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.0612073811121805

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7859380991428875

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
38.113699999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropylmaleic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00005634c28197f8>

HMDB0012241
     RDKit          3D
Isopropylmaleic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -1.8079   -1.3410   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3649    0.0593   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7129    1.0178   -1.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1150    0.0734    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9289    0.8506   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390    1.0206   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    1.8649   -0.9791 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629    0.3834    0.6475 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -0.8123    1.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -1.5660    1.9044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8078   -0.9817    1.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9655   -1.9943   -0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2357   -1.7711    0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692   -1.3375   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569    0.4333    0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    0.8110   -2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    2.0457   -0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8384    0.9483   -1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    1.4836   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0265   -0.0189    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0743   -1.1691    2.7269 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  8 20  1  0
 11 21  1  0
M  END
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PDB for #<Metabolite:0x00005634c28197f8>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -5.625   2.812   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.958   2.042   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -5.625   4.352   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.291   2.042   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.957   2.812   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.957   4.352   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.291   5.122   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.623   5.122   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.623   2.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.623   0.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.290   2.812   0.000  0.00  0.00           C+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00005634c28197f8>

COMPND    HMDB0012241
HETATM    1  C1  UNL     1      -1.808  -1.341  -0.341  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.365   0.059  -0.070  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.713   1.018  -1.170  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.115   0.073   0.262  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.929   0.851  -0.373  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.339   1.021  -0.223  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.943   1.865  -0.979  1.00  0.00           O  
HETATM    8  O2  UNL     1       3.163   0.383   0.647  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.548  -0.812   1.306  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.316  -1.566   1.904  1.00  0.00           O  
HETATM   11  O4  UNL     1       1.808  -0.982   1.781  1.00  0.00           O  
HETATM   12  H1  UNL     1      -0.965  -1.994  -0.659  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.236  -1.771   0.588  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.569  -1.338  -1.167  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.857   0.433   0.853  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.212   0.811  -2.135  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.485   2.046  -0.821  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.838   0.948  -1.286  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.418   1.484  -1.166  1.00  0.00           H  
HETATM   20  H9  UNL     1       4.027  -0.019   0.320  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.074  -1.169   2.727  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5    5    9
CONECT    5    6   19
CONECT    6    7    7    8
CONECT    8   20
CONECT    9   10   10   11
CONECT   11   21
END
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SMILES for #<Metabolite:0x00005634c28197f8>

CC(C)C(=C\C(O)=O)\C(O)=O
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INCHI for #<Metabolite:0x00005634c28197f8>

InChI=1S/C7H10O4/c1-4(2)5(7(10)11)3-6(8)9/h3-4H,1-2H3,(H,8,9)(H,10,11)/b5-3-
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Synonyms
ValueSource
2-IsopropylmaleateChEBI
beta-IsopropylmaleateChEBI
2-Isopropylmaleic acidGenerator
b-IsopropylmaleateGenerator
b-Isopropylmaleic acidGenerator
beta-Isopropylmaleic acidGenerator
Β-isopropylmaleateGenerator
Β-isopropylmaleic acidGenerator
IsopropylmaleateGenerator
Isopropylmaleic acidGenerator
(2Z)-2-(1-Methylethyl)-2-butenedioic acidHMDB
Molecular FormulaC7H10O4
Average Mass158.1519
Monoisotopic Mass158.057908808
IUPAC Name(2Z)-2-(propan-2-yl)but-2-enedioic acid
Traditional Name2-isopropylmaleic acid
CAS Registry NumberNot Available
SMILES
CC(C)C(=C\C(O)=O)\C(O)=O
InChI Identifier
InChI=1S/C7H10O4/c1-4(2)5(7(10)11)3-6(8)9/h3-4H,1-2H3,(H,8,9)(H,10,11)/b5-3-
InChI KeyNJMGRJLQRLFQQX-HYXAFXHYSA-N