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Showing NP-Card for Isobutyric acid (NP0000989)

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Record Information
Version2.0
Created at2006-02-23 12:29:19 UTC
Updated at2022-02-22 15:55:11 UTC
NP-MRD IDNP0000989
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsobutyric acid
DescriptionIsobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000 ). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000989 (Isobutyric acid)


  Mrv1652303262019152D          

  6  5  0  0  0  0            999 V2000
   -4.4864    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008    0.4464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719   -0.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
Download

3D MOL for NP0000989 (Isobutyric acid)

HMDB0001873
     RDKit          3D
Isobutyric acid
 14 13  0  0  0  0  0  0  0  0999 V2000
   -0.2790    1.2326    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441    0.2385   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.8103   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -0.3754   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -0.2231   -1.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190   -1.1073    0.5413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.7974    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733    2.1877    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    1.3541    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    0.7661   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -1.0172    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -1.7558   -0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793   -0.3619   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -0.9254    0.8611 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
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
Download

3D SDF for NP0000989 (Isobutyric acid)


  Mrv1652303262019152D          

  6  5  0  0  0  0            999 V2000
   -4.4864    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2008    0.4464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719   -0.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    0.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000989

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)

> <INCHI_KEY>
KQNPFQTWMSNSAP-UHFFFAOYSA-N

> <FORMULA>
C4H8O2

> <MOLECULAR_WEIGHT>
88.1051

> <EXACT_MASS>
88.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.116588155592677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpropanoic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
1.020176411

> <ALOGPS_LOGS>
0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.866878196732949

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
21.845100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isobutyric acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0000989 (Isobutyric acid)

HMDB0001873
     RDKit          3D
Isobutyric acid
 14 13  0  0  0  0  0  0  0  0999 V2000
   -0.2790    1.2326    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441    0.2385   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.8103   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020   -0.3754   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -0.2231   -1.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190   -1.1073    0.5413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.7974    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733    2.1877    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    1.3541    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    0.7661   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -1.0172    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -1.7558   -0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793   -0.3619   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -0.9254    0.8611 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
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
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PDB for NP0000989 (Isobutyric acid)

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0      -8.375   1.603   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.708   0.833   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -8.375   3.143   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.041   0.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.041  -0.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.707   1.603   0.000  0.00  0.00           C+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for NP0000989 (Isobutyric acid)

COMPND    HMDB0001873
HETATM    1  C1  UNL     1      -0.279   1.233   0.663  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.144   0.239  -0.467  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.222  -0.810  -0.272  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.202  -0.375  -0.516  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.892  -0.223  -1.555  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.719  -1.107   0.541  1.00  0.00           O  
HETATM    7  H1  UNL     1       0.257   0.797   1.536  1.00  0.00           H  
HETATM    8  H2  UNL     1       0.173   2.188   0.354  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.333   1.354   0.897  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.375   0.766  -1.399  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.406  -1.017   0.812  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.988  -1.756  -0.802  1.00  0.00           H  
HETATM   13  H7  UNL     1      -2.179  -0.362  -0.655  1.00  0.00           H  
HETATM   14  H8  UNL     1       2.683  -0.925   0.861  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4   10
CONECT    3   11   12   13
CONECT    4    5    5    6
CONECT    6   14
END
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SMILES for NP0000989 (Isobutyric acid)

CC(C)C(O)=O
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INCHI for NP0000989 (Isobutyric acid)

InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
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View in JSmol
Synonyms
ValueSource
2,2-Dimethylacetic acidChEBI
2-METHYL-propionIC ACIDChEBI
2-MethylpropanoateChEBI
2-Methylpropanoic acidChEBI
2-MethylpropionsaeureChEBI
alpha-Isobutyric acidChEBI
alpha-Methylpropanoic acidChEBI
alpha-Methylpropionic acidChEBI
Dimethylacetic acidChEBI
Iso-butyric acidChEBI
Iso-C3H7COOHChEBI
IsobutanoateChEBI
Isobutanoic acidChEBI
IsobuttersaeureChEBI
IsobutyrateChEBI
Isopropylformic acidChEBI
2,2-DimethylacetateGenerator
2-METHYL-propionateGenerator
a-IsobutyrateGenerator
a-Isobutyric acidGenerator
alpha-IsobutyrateGenerator
Α-isobutyrateGenerator
Α-isobutyric acidGenerator
a-MethylpropanoateGenerator
a-Methylpropanoic acidGenerator
alpha-MethylpropanoateGenerator
Α-methylpropanoateGenerator
Α-methylpropanoic acidGenerator
a-MethylpropionateGenerator
a-Methylpropionic acidGenerator
alpha-MethylpropionateGenerator
Α-methylpropionateGenerator
Α-methylpropionic acidGenerator
DimethylacetateGenerator
Iso-butyrateGenerator
IsopropylformateGenerator
2-MethylpropionateHMDB
2-Methylpropionic acidHMDB
I-butyrateHMDB
I-butyric acidHMDB
Ammonium isobutyrateHMDB
Isobutyric acid, ammonium saltHMDB
Isobutyric acid, sodium saltHMDB
2-Methpropanoic acidHMDB
Isobutyric acid, hemiammoniateHMDB
Sodium isobutyrateHMDB
Isobutyric acid, calcium saltHMDB
Isobutyric acid, nickel saltHMDB
Isobutyric acid, potassium saltHMDB
Isobutyric acid, sodium salt, 11C-labeledHMDB
Isobutyric acid, sodium salt, 14C-labeledHMDB
Isobutyric acidKEGG
Chemical FormulaC4H8O2
Average Mass88.1051 Da
Monoisotopic Mass88.05243 Da
IUPAC Name2-methylpropanoic acid
Traditional Nameisobutyric acid
CAS Registry Number79-31-2
SMILES
CC(C)C(O)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
InChI KeyKQNPFQTWMSNSAP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-03-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-03-28View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, 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
Actinidia chinensisLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Harvey J. Gold, Charles W. Wilson III The Volatile Flavor Substances of Celery. Journal of Food S...
Arctium lappaFooDB
Arnica montanaLOTUS Database
Bison bisonFooDB
Blattella germanicaLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Centipeda minimaLOTUS Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.Plant
ColumbaFooDB
ColumbidaeFooDB
Daphnia magnaLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Glycyrrhiza glabraLOTUS Database
Heracleum persicumLOTUS Database
Lagopus mutaFooDB
Lates calcariferLOTUS Database
Laurus nobilis L.FooDB
Lavandula angustifoliaLOTUS Database
LeporidaeFooDB
Lepus timidusFooDB
Lithospermum erythrorhizonKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha x piperitaFooDB
Morus albaKNApSAcK Database
Myrtus communisLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Pelargonium graveolensLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Polygala senegaLOTUS Database
Prunus armeniacaFooDB
Rubus idaeusFooDB
Scarites subterraneusLOTUS Database
Solanum pennelliiLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Thamnophis butleriLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility167 mg/mL at 20 °CNot Available
LogP0.94Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility197 g/LALOGPS
logP0.78ALOGPS
logP1.02ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.85 m³·mol⁻¹ChemAxon
Polarizability9.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001873
DrugBank IDDB02531
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003277
KNApSAcK IDC00029462
Chemspider ID6341
KEGG Compound IDC02632
BioCyc IDISOBUTYRATE
BiGG IDNot Available
Wikipedia LinkIsobutyric_acid
METLIN ID106
PubChem Compound6590
PDB IDNot Available
ChEBI ID16135
Good Scents IDrw1078691
References
General References
  1. Hoverstad T, Fausa O, Bjorneklett A, Bohmer T: Short-chain fatty acids in the normal human feces. Scand J Gastroenterol. 1984 May;19(3):375-81. [PubMed:6740214 ]
  2. Faed EM, McQueen EG: Separation of two conjugates of clofibric acid (CPIB) found in the urine of subjects taking clofibrate. Clin Exp Pharmacol Physiol. 1978 Mar-Apr;5(2):195-8. [PubMed:648038 ]
  3. Lang K, Zierow J, Buehler K, Schmid A: Metabolic engineering of Pseudomonas sp. strain VLB120 as platform biocatalyst for the production of isobutyric acid and other secondary metabolites. Microb Cell Fact. 2014 Jan 7;13:2. doi: 10.1186/1475-2859-13-2. [PubMed:24397404 ]