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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:34 UTC

Update Date

2020-02-26 21:23:46 UTC

HMDB ID

HMDB0002056

Secondary Accession Numbers

HMDB02056

Metabolite Identification

Common Name

Monoisobutyl phthalic acid

Description

Monoisobutyl phthalic acid is a phthalate metabolite that has been found in human meconium and in semen (PMID: 16970347 ), saliva (PMID: 15995852 ), and urine (PMID: 15113553 ). Phthalate esters are a family of multifunctional compounds widely used as plasticizers, solvents, or additives in many diverse products such as poly(vinyl chloride) (PVC) materials, pharmaceuticals and medical devices, pesticides, lubricants, and personal care products. Humans have been exposed to phthalates through the manufacture, ubiquitous use, and disposal of PVC materials and other phthalate-containing products. (PMID: 16970347 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0002056
     RDKit          3D
Monoisobutyl phthalic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4071   -0.7661    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600   -0.5695   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9347    0.8772   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0635   -0.8884    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -0.8528    0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1928    0.1699    0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091    1.3022    0.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6267   -0.1471    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -1.4811    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3314   -1.8780    0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -0.9308    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441    0.3912   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    0.8022    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    2.2099    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719    2.7746    0.0952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4371    3.0688   -0.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276   -1.8422    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3869   -0.3450    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.2027   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532   -1.2548   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.1007   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9467    1.1373   -1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120    1.5220    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097   -0.2218    1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550   -1.9157    1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744   -2.2375    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6046   -2.9056    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3570   -1.1701   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7230    1.1219   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851    3.1313    0.6138 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
M  END


  Mrv0541 02231219202D          

 16 16  0  0  0  0            999 V2000
   15.4010  -12.7462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9722  -12.7462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5431  -14.3962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2577  -13.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1157  -11.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4010  -11.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8301  -11.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1157  -10.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6866  -13.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6866  -13.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9722  -14.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4010  -14.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9722  -15.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4010  -15.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6866  -15.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2577  -13.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  2 10  2  0  0  0  0
  3 16  1  0  0  0  0
  4 16  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
 11 13  2  0  0  0  0
 11 16  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002056

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)COC(=O)C1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-8(2)7-16-12(15)10-6-4-3-5-9(10)11(13)14/h3-6,8H,7H2,1-2H3,(H,13,14)

> <INCHI_KEY>
RZJSUWQGFCHNFS-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.2372

> <EXACT_MASS>
222.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.831567964098728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2-methylpropoxy)carbonyl]benzoic acid

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.8786088640000003

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0846787952199533

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9569248152260705

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
59.083700000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
MIBP

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002056
     RDKit          3D
Monoisobutyl phthalic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4071   -0.7661    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600   -0.5695   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9347    0.8772   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0635   -0.8884    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -0.8528    0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1928    0.1699    0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091    1.3022    0.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6267   -0.1471    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -1.4811    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3314   -1.8780    0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -0.9308    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441    0.3912   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    0.8022    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    2.2099    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719    2.7746    0.0952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4371    3.0688   -0.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276   -1.8422    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3869   -0.3450    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.2027   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532   -1.2548   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.1007   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9467    1.1373   -1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120    1.5220    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097   -0.2218    1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550   -1.9157    1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744   -2.2375    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6046   -2.9056    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3570   -1.1701   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7230    1.1219   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851    3.1313    0.6138 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      28.749 -23.793   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.081 -23.793   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      23.414 -26.873   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      24.748 -24.563   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      30.083 -21.483   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.749 -22.253   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.416 -22.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.083 -19.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.415 -26.103   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.415 -24.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.081 -26.873   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.749 -26.873   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.081 -28.413   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.749 -28.413   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.415 -29.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.748 -26.103   0.000  0.00  0.00           C+0
CONECT    1    6   10                                                       
CONECT    2   10                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5    6    7    8                                                  
CONECT    6    1    5                                                       
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9   10   11   12                                                  
CONECT   10    1    2    9                                                  
CONECT   11    9   13   16                                                  
CONECT   12    9   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
CONECT   16    3    4   11                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0002056
HETATM    1  C1  UNL     1       4.407  -0.766   0.128  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.960  -0.569  -0.421  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.935   0.877  -0.828  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.063  -0.888   0.700  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.702  -0.853   0.571  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.193   0.170   0.372  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.309   1.302   0.303  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.627  -0.147   0.261  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.038  -1.481   0.325  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.331  -1.878   0.222  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.302  -0.931   0.045  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.944   0.391  -0.024  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.591   0.802   0.084  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.357   2.210   0.009  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.272   2.775   0.095  1.00  0.00           O  
HETATM   16  O4  UNL     1      -3.437   3.069  -0.181  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.628  -1.842   0.222  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.387  -0.345   1.154  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.123  -0.203  -0.468  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.853  -1.255  -1.288  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.144   1.101  -1.555  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.947   1.137  -1.314  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.912   1.522   0.068  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.410  -0.222   1.565  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.355  -1.916   1.097  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.274  -2.237   0.466  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.605  -2.906   0.276  1.00  0.00           H  
HETATM   28  H12 UNL     1      -5.357  -1.170  -0.046  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.723   1.122  -0.164  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.085   3.131   0.614  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21   22   23
CONECT    4    5   24   25
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   30
END

HMDB0002056
     RDKit          3D
Monoisobutyl phthalic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4071   -0.7661    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600   -0.5695   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9347    0.8772   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0635   -0.8884    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -0.8528    0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1928    0.1699    0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091    1.3022    0.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6267   -0.1471    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -1.4811    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3314   -1.8780    0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -0.9308    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441    0.3912   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    0.8022    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    2.2099    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719    2.7746    0.0952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4371    3.0688   -0.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276   -1.8422    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3869   -0.3450    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.2027   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532   -1.2548   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.1007   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9467    1.1373   -1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120    1.5220    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097   -0.2218    1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550   -1.9157    1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744   -2.2375    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6046   -2.9056    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3570   -1.1701   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7230    1.1219   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851    3.1313    0.6138 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  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Benzenedicarboxylic acid, mono(2-methylpropyl) ester	ChEBI
2-(Isobutoxycarbonyl)benzoic acid	ChEBI
Isobutyl hydrogen phthalate	ChEBI
MIBP	ChEBI
mono-Iso-butyl phthalate	ChEBI
Phthalic acid, monoisobutyl ester	ChEBI
1,2-Benzenedicarboxylate, mono(2-methylpropyl) ester	Generator
2-(Isobutoxycarbonyl)benzoate	Generator
Isobutyl hydrogen phthalic acid	Generator
mono-Iso-butyl phthalic acid	Generator
Phthalate, monoisobutyl ester	Generator
Monoisobutyl phthalate	Generator
Monoisobutyl phthalic acid	ChEBI

Chemical Formula

C₁₂H₁₄O₄

Average Molecular Weight

222.2372

Monoisotopic Molecular Weight

222.089208936

IUPAC Name

2-[(2-methylpropoxy)carbonyl]benzoic acid

Traditional Name

MIBP

CAS Registry Number

30833-53-5

SMILES

CC(C)COC(=O)C1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C12H14O4/c1-8(2)7-16-12(15)10-6-4-3-5-9(10)11(13)14/h3-6,8H,7H2,1-2H3,(H,13,14)

InChI Key

RZJSUWQGFCHNFS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoic acid
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15995852)
Saliva (PMID: 15995852)

Cellular substructure

Membrane (HMDB: HMDB0002056)
Cell membrane (HMDB: HMDB0002056)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002056)

Source

Endogenous

Endogenous (HMDB: HMDB0002056)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.88	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.08 m³·mol⁻¹	ChemAxon
Polarizability	22.83 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.698	31661259
DarkChem	[M-H]-	148.581	31661259
DeepCCS	[M+H]+	147.456	30932474
DeepCCS	[M-H]-	144.093	30932474
DeepCCS	[M-2H]-	180.593	30932474
DeepCCS	[M+Na]+	156.131	30932474
AllCCS	[M+H]+	148.8	32859911
AllCCS	[M+H-H2O]+	145.0	32859911
AllCCS	[M+NH4]+	152.3	32859911
AllCCS	[M+Na]+	153.3	32859911
AllCCS	[M-H]-	150.6	32859911
AllCCS	[M+Na-2H]-	151.0	32859911
AllCCS	[M+HCOO]-	151.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.58 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6083 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.4 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2272.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	399.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	592.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	710.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1046.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	448.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1448.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	463.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	347.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	315.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	41.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Monoisobutyl phthalic acid	CC(C)COC(=O)C1=CC=CC=C1C(O)=O	2752.5	Standard polar	33892256
Monoisobutyl phthalic acid	CC(C)COC(=O)C1=CC=CC=C1C(O)=O	1718.7	Standard non polar	33892256
Monoisobutyl phthalic acid	CC(C)COC(=O)C1=CC=CC=C1C(O)=O	1797.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Monoisobutyl phthalic acid,1TMS,isomer #1	CC(C)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C	1788.6	Semi standard non polar	33892256
Monoisobutyl phthalic acid,1TBDMS,isomer #1	CC(C)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2014.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Monoisobutyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4910000000-ac2484b74eb5cfd5b690	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoisobutyl phthalic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6390000000-4ca9de5bf766a991b3dc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoisobutyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoisobutyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoisobutyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-0089-0930000000-d249a5cd21193a8a3cd2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoisobutyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-13d64e3eb0a1e3e235be	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoisobutyl phthalic acid 35V, Negative-QTOF	splash10-0089-0930000000-3a306e5ce6ca6a0e9127	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoisobutyl phthalic acid 35V, Positive-QTOF	splash10-0002-0900000000-b4a2e5d94dccaced84c1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 10V, Positive-QTOF	splash10-0ab9-6690000000-8f32418bd6ccde0549c0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 20V, Positive-QTOF	splash10-0a4i-9720000000-286cdd7561a043eef3d0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 40V, Positive-QTOF	splash10-0a4i-9500000000-6c3aca6817c2db6bb804	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 10V, Negative-QTOF	splash10-00di-1790000000-2d20ca2ec96d84986321	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 20V, Negative-QTOF	splash10-0100-2910000000-46c6c191f37b2782021a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 40V, Negative-QTOF	splash10-00di-6900000000-0d9a0ca1ebdbc964dac0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 10V, Positive-QTOF	splash10-0a4j-0940000000-827565da796a34bbd6b1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 20V, Positive-QTOF	splash10-052b-1900000000-bfe543859b406a2dae92	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 40V, Positive-QTOF	splash10-0a4i-2900000000-8cb1cf43ad6057fc27c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 10V, Negative-QTOF	splash10-00b9-0930000000-2a9d225bebcec6f94629	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 20V, Negative-QTOF	splash10-004i-6910000000-2ae4c65b2cf89d2dde5a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoisobutyl phthalic acid 40V, Negative-QTOF	splash10-004i-9200000000-c321d909ae49bc32f15a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0022 (0.0-0.0044) uM	Adult (>18 years old)	Both	Normal	15995852	details
Saliva	Detected and Quantified	0.0805 uM	Adult (>18 years old)	Both	Normal	15995852	details
Urine	Detected and Quantified	0.00379 (0.00346-0.00415) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.00672 (0.00600-0.00758) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022820

KNApSAcK ID

Not Available

Chemspider ID

83306

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92272

PDB ID

Not Available

ChEBI ID

90038

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ke, Changying. Esterification synthesis of diisobutyl phthalate. Huaxue Shijie (1986), 27(10), 440-2.

Material Safety Data Sheet (MSDS)

Not Available

General References

Silva MJ, Reidy JA, Samandar E, Herbert AR, Needham LL, Calafat AM: Detection of phthalate metabolites in human saliva. Arch Toxicol. 2005 Nov;79(11):647-52. Epub 2005 Jul 2. [PubMed:15995852 ]
Silva MJ, Slakman AR, Reidy JA, Preau JL Jr, Herbert AR, Samandar E, Needham LL, Calafat AM: Analysis of human urine for fifteen phthalate metabolites using automated solid-phase extraction. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jun 5;805(1):161-7. [PubMed:15113553 ]
Kato K, Silva MJ, Needham LL, Calafat AM: Quantifying phthalate metabolites in human meconium and semen using automated off-line solid-phase extraction coupled with on-line SPE and isotope-dilution high-performance liquid chromatography--tandem mass spectrometry. Anal Chem. 2006 Sep 15;78(18):6651-5. [PubMed:16970347 ]

Showing metabocard for Monoisobutyl phthalic acid (HMDB0002056)

MOL for HMDB0002056 (Monoisobutyl phthalic acid)

3D MOL for HMDB0002056 (Monoisobutyl phthalic acid)

3D SDF for HMDB0002056 (Monoisobutyl phthalic acid)

3D-SDF for HMDB0002056 (Monoisobutyl phthalic acid)

PDB for HMDB0002056 (Monoisobutyl phthalic acid)

3D PDB for HMDB0002056 (Monoisobutyl phthalic acid)

SMILES for HMDB0002056 (Monoisobutyl phthalic acid)

INCHI for HMDB0002056 (Monoisobutyl phthalic acid)

Structure for HMDB0002056 (Monoisobutyl phthalic acid)

3D Structure for HMDB0002056 (Monoisobutyl phthalic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra