NP-MRD: Showing NP-Card for Monoisobutyl phthalic acid (NP0086855)

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Record Information

Version

2.0

Created at

2022-05-11 16:32:54 UTC

Updated at

2022-05-11 16:32:54 UTC

NP-MRD ID

NP0086855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monoisobutyl phthalic acid

Description

Monoisobutyl phthalic acid, also known as isobutyl hydrogen phthalate or MIBP, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Monoisobutyl phthalic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Monoisobutyl phthalic acid is a potentially toxic compound. Monoisobutyl phthalic acid was first documented in 2004 (PMID: 15113553). A phthalic acid monoester obtained by formal condensation of one of the carboxy groups of phthalic acid with the hydroxy group of isobutanol (PMID: 15995852) (PMID: 25558797) (PMID: 25938866).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    4.2957   -0.3072    0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8517   -0.6899    0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5267   -1.9140   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    0.5065   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    0.2723    0.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    1.1370   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571    2.2481   -0.6818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7960    1.0140    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858    2.0861   -0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9361    2.0955   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5769    1.0077    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257   -0.0515    0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351   -0.0823    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7328   -1.2486    0.9662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4564   -2.2106    1.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -1.5267    0.9807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3681   -0.1835   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4621    0.6824    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.0771    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7835   -0.8857    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -2.8351    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2313   -1.9923   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5173   -1.7648   -0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2922    1.3791    0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2496    0.7941   -1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188    2.9628   -0.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5549    2.9510   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6711    0.9881    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3268   -0.9318    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0090   -2.4237    0.8255 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 16  1  0
 14 15  2  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>
NP0086855

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

222.2372 Da

Monoisotopic Mass

222.08921 Da

IUPAC Name

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

Traditional Name

MIBP

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0002056

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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. doi: 10.1016/j.jchromb.2004.02.038. [PubMed:15113553 ]
Valvi D, Monfort N, Ventura R, Casas M, Casas L, Sunyer J, Vrijheid M: Variability and predictors of urinary phthalate metabolites in Spanish pregnant women. Int J Hyg Environ Health. 2015 Mar;218(2):220-31. doi: 10.1016/j.ijheh.2014.11.003. Epub 2014 Dec 3. [PubMed:25558797 ]
Zhang H, Zhang Z, Nakanishi T, Wan Y, Hiromori Y, Nagase H, Hu J: Structure-dependent activity of phthalate esters and phthalate monoesters binding to human constitutive androstane receptor. Chem Res Toxicol. 2015 Jun 15;28(6):1196-204. doi: 10.1021/acs.chemrestox.5b00028. Epub 2015 May 13. [PubMed:25938866 ]

Showing NP-Card for Monoisobutyl phthalic acid (NP0086855)

MOL for NP0086855 (Monoisobutyl phthalic acid)

3D MOL for NP0086855 (Monoisobutyl phthalic acid)

3D SDF for NP0086855 (Monoisobutyl phthalic acid)

3D-SDF for NP0086855 (Monoisobutyl phthalic acid)

PDB for NP0086855 (Monoisobutyl phthalic acid)

3D PDB for NP0086855 (Monoisobutyl phthalic acid)

SMILES for NP0086855 (Monoisobutyl phthalic acid)

INCHI for NP0086855 (Monoisobutyl phthalic acid)

Structure for NP0086855 (Monoisobutyl phthalic acid)

3D Structure for NP0086855 (Monoisobutyl phthalic acid)