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Showing NP-Card for Isovaleric acid (NP0000073)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:50 UTC
NP-MRD IDNP0000073
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsovaleric acid
DescriptionIsovaleric acid, is a natural fatty acid found in a wide variety of plants and essential oils. Isovaleric acid is clear colorless liquid that is sparingly soluble in water, but well soluble in most common organic solvents. It has been suggested that isovaleric acid from pilot whales, a species frequently consumed in the Faroe Islands, may be the unusual dietary factor in prolonged gestation in the population of the Faroe Islands. Previous studies suggested that was due to the high intake of n-3 polyunsaturated fatty acids has been, but fatty acid data for eicosapentaenoic acid (EPA) and docosahexanoic acid (DHA) in blood lipids of Faroese and Norwegians was reviewed in terms of the type of fish eaten (mostly lean white fish with DHA much greater than EPA); the popular lean fish, thus, probably provides too little EPA to produce a marked effect on human biochemistry (PMID 2646392 ). Isovaleric acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000073 (Isovaleric acid)


  Mrv1652309272007312D          

  7  6  0  0  0  0            999 V2000
   -1.5400   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546   -0.4241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400    0.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256   -0.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -0.4241    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
  5  6  1  0  0  0  0
  5  7  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 NP0000073 (Isovaleric acid)

HMDB0000718
     RDKit          3D
Isovaleric acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.1041   -1.0778    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    0.1879    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598    1.3389    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    0.3330   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -0.8243   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697   -1.8835   -1.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261   -0.7437    0.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -1.9728    0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521   -1.0593   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195   -1.0444    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059    0.1713    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    1.0227   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858    1.5468    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    2.2247   -0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    1.2553   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    0.4245   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.1007    0.5245 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  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

3D SDF for NP0000073 (Isovaleric acid)


  Mrv1652309272007312D          

  7  6  0  0  0  0            999 V2000
   -1.5400   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546   -0.4241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400    0.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256   -0.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -0.4241    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
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000073

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)

> <INCHI_KEY>
GWYFCOCPABKNJV-UHFFFAOYSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
10.986666365215886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylbutanoic acid

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.208777894

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.01023295557517

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.4202

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovaleric acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000073 (Isovaleric acid)

HMDB0000718
     RDKit          3D
Isovaleric acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.1041   -1.0778    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    0.1879    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598    1.3389    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204    0.3330   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -0.8243   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697   -1.8835   -1.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261   -0.7437    0.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -1.9728    0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521   -1.0593   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195   -1.0444    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059    0.1713    1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747    1.0227   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858    1.5468    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    2.2247   -0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    1.2553   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    0.4245   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.1007    0.5245 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  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

PDB for NP0000073 (Isovaleric acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -2.875  -0.022   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.209  -0.792   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -2.875   1.518   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.541  -0.792   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.207  -0.022   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.207   1.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.126  -0.792   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0000073 (Isovaleric acid)

COMPND    HMDB0000718
HETATM    1  C1  UNL     1      -1.104  -1.078   0.305  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.287   0.188   0.423  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.260   1.339   0.281  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.720   0.333  -0.697  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.620  -0.824  -0.629  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.270  -1.883  -1.169  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.826  -0.744   0.017  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.464  -1.973   0.388  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.752  -1.059  -0.598  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.819  -1.044   1.176  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.206   0.171   1.421  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.075   1.023  -0.419  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.686   1.547   1.276  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.784   2.225  -0.156  1.00  0.00           H  
HETATM   15  H8  UNL     1       1.323   1.255  -0.483  1.00  0.00           H  
HETATM   16  H9  UNL     1       0.187   0.424  -1.660  1.00  0.00           H  
HETATM   17  H10 UNL     1       3.078   0.101   0.525  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4   11
CONECT    3   12   13   14
CONECT    4    5   15   16
CONECT    5    6    6    7
CONECT    7   17
END
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SMILES for NP0000073 (Isovaleric acid)

CC(C)CC(O)=O
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INCHI for NP0000073 (Isovaleric acid)

InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
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View in JSmol
Synonyms
ValueSource
3-Methyl-N-butyric acidChEBI
3-Methylbutanoic acidChEBI
3-MethylbuttersaeureChEBI
3-Methylbutyric acidChEBI
beta-Methylbutyric acidChEBI
Delphinic acidChEBI
Isobutylformic acidChEBI
Isopentanoic acidChEBI
Isopropylacetic acidChEBI
IsovalerateChEBI
Isovalerianic acidChEBI
IsovaleriansaeureChEBI
3-Methyl-N-butyrateGenerator
3-MethylbutanoateGenerator
3-MethylbutyrateGenerator
b-MethylbutyrateGenerator
b-Methylbutyric acidGenerator
beta-MethylbutyrateGenerator
Β-methylbutyrateGenerator
Β-methylbutyric acidGenerator
DelphinateGenerator
IsobutylformateGenerator
IsopentanoateGenerator
IsopropylacetateGenerator
IsovalerianateGenerator
3-Methyl butyric acidHMDB
3-Methylbutyric acid: isopropyl-acetateHMDB
3-Methylbutyric acid: isopropyl-acetic acidHMDB
3-Methyl-1-butanoic acidHMDB
Isovaleric acidKEGG
Chemical FormulaC5H10O2
Average Mass102.1317 Da
Monoisotopic Mass102.06808 Da
IUPAC Name3-methylbutanoic acid
Traditional Nameisovaleric acid
CAS Registry Number503-74-2
SMILES
CC(C)CC(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyGWYFCOCPABKNJV-UHFFFAOYSA-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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-07-25View Spectrum
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumKNApSAcK Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apium graveolensFooDB
Arctium lappaKNApSAcK Database
Artemisia carvifoliaLOTUS Database
Artemisia jacuticaLOTUS Database
Artemisia macrocephalaLOTUS Database
Bison bisonFooDB
Blattella germanicaLOTUS Database
Blepharocalyx salicifoliusLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Carthamus tinctoriusKNApSAcK Database
Centaurea orientalisKNApSAcK Database
Centranthus macrosiphonLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Cinnamomum aromaticumFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.Plant
ColumbaFooDB
ColumbidaeFooDB
Croton megalobotrysLOTUS Database
Curio articulatusLOTUS Database
Cymbopogon citratusFooDB
Delphinus delphis-
Dromaius novaehollandiaeFooDB
Elsholtzia ciliataKNApSAcK Database
Equus caballusFooDB
Euonymus japonicusKNApSAcK Database
Fragaria x ananassaLOTUS Database
Gallus gallusFooDB
Glycine maxFooDB
Goupia glabraLOTUS Database
Homo sapiensLOTUS Database
Humulus lupulusKNApSAcK Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Lithospermum erythrorhizonKNApSAcK Database
Litsea cubebaKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha arvensisFooDB
Mentha x piperitaFooDB
Micromelum minutumPlant
Morus albaKNApSAcK Database
Musa x paradisiacaFooDB
Nardostachys chinensisKNApSAcK Database
Nardostachys jatamansiPlant
Nicotiana tabacumKNApSAcK Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Pelargonium graveolensLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Piper nigrum L.FooDB
Pittosporum undulatumLOTUS Database
Plantago lanceolataPlant
Polygala senegaLOTUS Database
Prunus cerasusFooDB
Prunus domesticaLOTUS Database
Prunus persicaFooDB
Rubus idaeusFooDB
Saxifraga stoloniferaLOTUS Database
Saxifraga stolonifera Meerb.KNApSAcK Database
Solanum lycopersicumKNApSAcK Database
Solanum pennelliiLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Thamnophis butleriLOTUS Database
Trypanosoma bruceiLOTUS Database
Vaccinium angustifoliumLOTUS Database
Valeriana celticaLOTUS Database
Valeriana officinalisKNApSAcK Database
Valeriana spp.KNApSAcK Database
Viburnum prunifoliumLOTUS Database
Vitis viniferaLOTUS Database
Xanthium strumariumLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Skin microbiota)KNApSAcK Database
Homo sapiens (Skin)KNApSAcK Database
Staphylococcus aureusKNApSAcK Database
Chemical Taxonomy
Description 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 only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • 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-29.3 °CNot Available
Boiling Point175.00 to 177.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility40.7 mg/mLNot Available
LogP1.16Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility64.9 g/LALOGPS
logP1.26ALOGPS
logP1.21ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.42 m³·mol⁻¹ChemAxon
Polarizability10.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000718
DrugBank IDDB03750
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001324
KNApSAcK IDC00001189
Chemspider ID10001
KEGG Compound IDC08262
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylbutanoic acid
METLIN ID109
PubChem Compound10430
PDB IDNot Available
ChEBI ID28484
Good Scents IDrw1056411
References
General References
  1. Silva MF, Selhorst J, Overmars H, van Gennip AH, Maya M, Wanders RJ, de Almeida IT, Duran M: Characterization of plasma acylcarnitines in patients under valproate monotherapy using ESI-MS/MS. Clin Biochem. 2001 Nov;34(8):635-8. [PubMed:11849623 ]
  2. Arthur K, Hommes FA: Simple isotope dilution assay for propionic acid and isovaleric acid. J Chromatogr B Biomed Appl. 1995 Nov 3;673(1):132-5. [PubMed:8925066 ]
  3. Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F: Foot odor due to microbial metabolism and its control. Can J Microbiol. 2006 Apr;52(4):357-64. [PubMed:16699586 ]
  4. Ackman RG: Birthweights in the Faroe Islands: possible role of isovaleric acid. J Intern Med. 1989 Feb;225(2):73-5. [PubMed:2646392 ]