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Showing metabocard for Isocaproic acid (HMDB0000689)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:04 UTC
HMDB IDHMDB0000689
Secondary Accession Numbers
  • HMDB00689
Metabolite Identification
Common NameIsocaproic acid
DescriptionIsocaproic acid, also known as 4-methyl-valerate or isohexanoic 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 only one or more methyl group. However, branches other than methyl may be present. Based on a literature review a significant number of articles have been published on Isocaproic acid.
Structure
Data?1676999704
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000689 (Isocaproic acid)


  Mrv1652305271900172D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for HMDB0000689 (Isocaproic acid)

HMDB0000689
     RDKit          3D
Isocaproic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -1.2393    1.0867   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -0.3588   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3137   -0.8999   -0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -0.4106    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405    0.1691   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.1689    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3640   -0.2749    1.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7305    0.6436    0.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    1.2109   -1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    1.3082   -1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0414    1.7664   -0.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7452   -0.9149   -1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613   -1.4190   -0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -1.6642    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9893   -0.1484    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051    0.2354    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987   -1.4530    0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    1.2020   -0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5260   -0.4423   -1.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949    0.1949   -0.4393 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
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  END
Download

3D SDF for HMDB0000689 (Isocaproic acid)


  Mrv1652305271900172D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000689

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3,(H,7,8)

> <INCHI_KEY>
FGKJLKRYENPLQH-UHFFFAOYSA-N

> <FORMULA>
C6H12O2

> <MOLECULAR_WEIGHT>
116.1583

> <EXACT_MASS>
116.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.062697113252494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylpentanoic acid

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.6533465589999996

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.090081586138642

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
31.0212

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isocaproate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000689 (Isocaproic acid)

HMDB0000689
     RDKit          3D
Isocaproic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -1.2393    1.0867   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -0.3588   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3137   -0.8999   -0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -0.4106    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405    0.1691   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.1689    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3640   -0.2749    1.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7305    0.6436    0.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    1.2109   -1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    1.3082   -1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0414    1.7664   -0.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7452   -0.9149   -1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613   -1.4190   -0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -1.6642    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9893   -0.1484    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051    0.2354    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987   -1.4530    0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406    1.2020   -0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5260   -0.4423   -1.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949    0.1949   -0.4393 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
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  END
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PDB for HMDB0000689 (Isocaproic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   3.644   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0000689 (Isocaproic acid)

COMPND    HMDB0000689
HETATM    1  C1  UNL     1      -1.239   1.087  -0.974  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.026  -0.359  -0.574  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.314  -0.900  -0.024  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.098  -0.411   0.453  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.340   0.169  -0.228  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.500   0.169   0.679  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.364  -0.275   1.838  1.00  0.00           O  
HETATM    8  O2  UNL     1       3.731   0.644   0.288  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.261   1.211  -1.384  1.00  0.00           H  
HETATM   10  H2  UNL     1      -0.506   1.308  -1.776  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.041   1.766  -0.116  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.745  -0.915  -1.492  1.00  0.00           H  
HETATM   13  H5  UNL     1      -2.861  -1.419  -0.855  1.00  0.00           H  
HETATM   14  H6  UNL     1      -2.104  -1.664   0.749  1.00  0.00           H  
HETATM   15  H7  UNL     1      -2.989  -0.148   0.385  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.205   0.235   1.301  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.299  -1.453   0.771  1.00  0.00           H  
HETATM   18  H10 UNL     1       1.141   1.202  -0.577  1.00  0.00           H  
HETATM   19  H11 UNL     1       1.526  -0.442  -1.148  1.00  0.00           H  
HETATM   20  H12 UNL     1       4.295   0.195  -0.439  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    4   12
CONECT    3   13   14   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7    7    8
CONECT    8   20
END
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SMILES for HMDB0000689 (Isocaproic acid)

CC(C)CCC(O)=O
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INCHI for HMDB0000689 (Isocaproic acid)

InChI=1S/C6H12O2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3,(H,7,8)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4,4-Dimethylbutanoic acidChEBI
4-Methyl-N-valeric acidChEBI
4-Methyl-pentanoic acidChEBI
4-Methyl-valeric acidChEBI
4-Methylvaleric acidChEBI
Isobutylacetic acidChEBI
Isohexanoic acidChEBI
Isohexoic acidChEBI
4,4-DimethylbutanoateGenerator
4-Methyl-N-valerateGenerator
4-Methyl-pentanoateGenerator
4-Methyl-valerateGenerator
4-MethylvalerateGenerator
IsobutylacetateGenerator
IsohexanoateGenerator
IsohexoateGenerator
IsocaproateGenerator
4-MethylpentanoateHMDB
4-Methylpentanoic acidHMDB
Isocaproic acid, sodium saltHMDB
4-Methyl valerateHMDB
Isocaproic acidMeSH
Chemical FormulaC6H12O2
Average Molecular Weight116.1583
Monoisotopic Molecular Weight116.083729628
IUPAC Name4-methylpentanoic acid
Traditional Nameisocaproate
CAS Registry Number646-07-1
SMILES
CC(C)CCC(O)=O
InChI Identifier
InChI=1S/C6H12O2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3,(H,7,8)
InChI KeyFGKJLKRYENPLQH-UHFFFAOYSA-N
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
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-33 °CNot Available
Boiling Point199.00 to 201.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility5266 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.560 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg127.4830932474
[M-H]-Not Available127.48http://allccs.zhulab.cn/database/detail?ID=AllCCS00000207
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.9 g/LALOGPS
logP1.72ALOGPS
logP1.65ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)5.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.02 m³·mol⁻¹ChemAxon
Polarizability13.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.62131661259
DarkChem[M-H]-119.97531661259
AllCCS[M+H]+127.60632859911
AllCCS[M-H]-128.89432859911
DeepCCS[M+H]+133.34130932474
DeepCCS[M-H]-130.5830932474
DeepCCS[M-2H]-167.0130932474
DeepCCS[M+Na]+141.79530932474
AllCCS[M+H]+127.632859911
AllCCS[M+H-H2O]+123.432859911
AllCCS[M+NH4]+131.632859911
AllCCS[M+Na]+132.732859911
AllCCS[M-H]-128.932859911
AllCCS[M+Na-2H]-132.232859911
AllCCS[M+HCOO]-135.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.3.04 minutes32390414
Predicted by Siyang on May 30, 202212.3121 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.68 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid36.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1607.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid406.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid137.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid258.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid165.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid483.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid514.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)126.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid928.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid366.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1184.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid311.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid345.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate422.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA372.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water90.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isocaproic acidCC(C)CCC(O)=O1777.0Standard polar33892256
Isocaproic acidCC(C)CCC(O)=O917.2Standard non polar33892256
Isocaproic acidCC(C)CCC(O)=O973.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isocaproic acid,1TMS,isomer #1CC(C)CCC(=O)O[Si](C)(C)C1039.7Semi standard non polar33892256
Isocaproic acid,1TBDMS,isomer #1CC(C)CCC(=O)O[Si](C)(C)C(C)(C)C1257.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isocaproic acid EI-B (Non-derivatized)splash10-0abc-9000000000-9da80434be2ce0d869132017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocaproic acid EI-B (Non-derivatized)splash10-0abc-9000000000-9da80434be2ce0d869132018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocaproic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-409421423ee1195a98612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocaproic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-9b8596f9372ec51c4c6f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocaproic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocaproic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0abc-9000000000-a381f69e01ac46730bd42015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014j-6900000000-cb7997a5c6ca2f6418c72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00gi-9100000000-da8f07a6e124535385f02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001d-7900000000-d997ac31e14c8967a6332012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0abc-9000000000-9da80434be2ce0d869132012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-f28fa3474851e17f83b42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-014i-0900000000-6e23bff66db2ce8e669a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-03di-4900000000-853711a3867735db4fa22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-f28fa3474851e17f83b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-4cb9b0933d7d0630adb32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid LC-ESI-QQ , negative-QTOFsplash10-03di-4900000000-853711a3867735db4fa22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid 40V, Negative-QTOFsplash10-03di-7900000000-3f3b376f8c98cd66f69e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid 20V, Negative-QTOFsplash10-00di-9000000000-45d86acaf64ede34d93d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid 10V, Positive-QTOFsplash10-001i-9200000000-6faff2e6cf28aed811d72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid 20V, Positive-QTOFsplash10-001i-9000000000-38ab740b75f1ee9f2c502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid 10V, Negative-QTOFsplash10-066r-9700000000-fa5e5239effdaa850e062021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocaproic acid 40V, Positive-QTOFsplash10-004i-9000000000-8f3314179f36255824da2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 10V, Positive-QTOFsplash10-0002-9200000000-a87d3af0796b3929b5852015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 20V, Positive-QTOFsplash10-006t-9100000000-0dd3655055a4bd052af42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-5a494f4ea95bbce2ac3e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 10V, Negative-QTOFsplash10-014i-4900000000-9419bcb9bb04937d30062015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 20V, Negative-QTOFsplash10-01ba-9400000000-d7efbb09535c4b1344f22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 40V, Negative-QTOFsplash10-0a4l-9000000000-a61c06d9d6e46707a0a02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 10V, Positive-QTOFsplash10-0597-9000000000-bc541e0a6062f4aa04b02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 20V, Positive-QTOFsplash10-0a4l-9000000000-410be7ca108e80fbdcb12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaproic acid 40V, Positive-QTOFsplash10-0006-9000000000-37ca7fdfa7a7c672f62b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified10-70 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified0-41868.152 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified1695.961 +/- 581.104 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected and Quantified20.489 +/- 11.536 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
SalivaDetected and Quantified43.65 +/- 44.98 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableMaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected and Quantified0-11277.713 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDs
DrugBank IDDB03993
Phenol Explorer Compound IDNot Available
FooDB IDFDB008206
KNApSAcK IDC00050474
Chemspider ID12067
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Methylpentanoic acid
METLIN ID4191
PubChem Compound12587
PDB IDNot Available
ChEBI ID74903
Food Biomarker OntologyNot Available
VMH IDISOCAPR
MarkerDB IDMDB00029883
Good Scents IDrw1036331
References
Synthesis ReferenceShimizu, K.; Dorfman, Ralph I.; Gut, Marcel. Isocaproic acid, a metabolite of 20a-hydroxycholesterol. Journal of Biological Chemistry (1960), 235 PC25.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. SHIMIZU K, DORFMAN RI, GUT M: Isocaproic acid, a metabolite of 20 alpha-hydroxycholesterol. J Biol Chem. 1960 Jun;235:PC25. [PubMed:14446007 ]
  2. Loganath A, Peh KL, Wong PC: Evidence for the biosynthesis of DHEA from cholesterol by first-trimester human placental tissue: source of androgens. Horm Metab Res. 2002 Mar;34(3):116-20. [PubMed:11972299 ]