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Showing metabocard for Isovaleraldehyde (HMDB0006478)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-23 11:08:59 UTC
Update Date2023-02-21 17:17:19 UTC
HMDB IDHMDB0006478
Secondary Accession Numbers
  • HMDB0240630
  • HMDB06478
Metabolite Identification
Common NameIsovaleraldehyde
DescriptionIso-Valeraldehyde, also known as isoamyl aldehyde or 3-methyl-butanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. Iso-Valeraldehyde exists in all eukaryotes, ranging from yeast to humans. Iso-Valeraldehyde is an aldehydic, chocolate, and ethereal tasting compound. Iso-Valeraldehyde is found, on average, in the highest concentration within a few different foods, such as milk (cow), beers, and taco and in a lower concentration in kohlrabis, corns, and tortilla. Iso-Valeraldehyde has also been detected, but not quantified, in several different foods, such as muskmelons, highbush blueberries, fenugreeks, hazelnuts, and dills. This could make iso-valeraldehyde a potential biomarker for the consumption of these foods. A methylbutanal that is butanal substituted by a methyl group at position 3. Iso-Valeraldehyde, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, crohn's disease, perillyl alcohol administration for cancer treatment, and hepatic encephalopathy; iso-valeraldehyde has also been linked to the inborn metabolic disorder celiac disease.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006478 (Isovaleraldehyde)

  Mrv1652309272007312D          

  6  5  0  0  0  0            999 V2000
    0.1212   -0.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5955    0.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344    0.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3123   -0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990    0.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5511   -0.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
M  END
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3D MOL for HMDB0006478 (Isovaleraldehyde)

HMDB0006478
     RDKit          3D
Isovaleraldehyde
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.7176    1.2283    0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4432   -0.2297    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0983   -0.6853   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130   -0.5810    0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    0.0929   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610   -0.1480   -0.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.3500    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995    1.6350    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    1.8356   -0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -0.7776    1.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626   -1.6975   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -0.0181   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4282   -0.7453   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196   -0.3667    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -1.6752    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    0.7825   -1.3283 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
  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
  4 14  1  0
  4 15  1  0
  5 16  1  0
M  END
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3D SDF for HMDB0006478 (Isovaleraldehyde)

  Mrv1652309272007312D          

  6  5  0  0  0  0            999 V2000
    0.1212   -0.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5955    0.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344    0.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3123   -0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990    0.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5511   -0.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006478

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3

> <INCHI_KEY>
YGHRJJRRZDOVPD-UHFFFAOYSA-N

> <FORMULA>
C5H10O

> <MOLECULAR_WEIGHT>
86.1323

> <EXACT_MASS>
86.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.12084477416142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylbutanal

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.0501616416666666

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.56011290069315

> <JCHEM_PKA_STRONGEST_BASIC>
-6.950085545908737

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
25.494799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovaleraldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0006478 (Isovaleraldehyde)

HMDB0006478
     RDKit          3D
Isovaleraldehyde
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.7176    1.2283    0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4432   -0.2297    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0983   -0.6853   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130   -0.5810    0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    0.0929   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610   -0.1480   -0.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.3500    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995    1.6350    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    1.8356   -0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -0.7776    1.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626   -1.6975   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -0.0181   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4282   -0.7453   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196   -0.3667    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -1.6752    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    0.7825   -1.3283 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
  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
  4 14  1  0
  4 15  1  0
  5 16  1  0
M  END
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PDB for HMDB0006478 (Isovaleraldehyde)

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       0.226  -0.640   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.112   0.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.558   0.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.450  -0.646   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.118   1.667   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.895  -0.633   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1    6                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    3                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0006478 (Isovaleraldehyde)

COMPND    HMDB0006478
HETATM    1  C1  UNL     1      -0.718   1.228   0.668  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.443  -0.230   0.474  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.098  -0.685  -0.786  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.013  -0.581   0.456  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.767   0.093  -0.620  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.961  -0.148  -0.693  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.818   1.350   0.753  1.00  0.00           H  
HETATM    8  H2  UNL     1      -0.299   1.635   1.622  1.00  0.00           H  
HETATM    9  H3  UNL     1      -0.411   1.836  -0.211  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.905  -0.778   1.324  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.563  -1.698  -0.648  1.00  0.00           H  
HETATM   12  H6  UNL     1      -1.946  -0.018  -1.066  1.00  0.00           H  
HETATM   13  H7  UNL     1      -0.428  -0.745  -1.654  1.00  0.00           H  
HETATM   14  H8  UNL     1       1.520  -0.367   1.422  1.00  0.00           H  
HETATM   15  H9  UNL     1       1.088  -1.675   0.287  1.00  0.00           H  
HETATM   16  H10 UNL     1       1.281   0.783  -1.328  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4   10
CONECT    3   11   12   13
CONECT    4    5   14   15
CONECT    5    6    6   16
END
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SMILES for HMDB0006478 (Isovaleraldehyde)

CC(C)CC=O
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INCHI for HMDB0006478 (Isovaleraldehyde)

InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H10O
Average Molecular Weight86.1323
Monoisotopic Molecular Weight86.073164942
IUPAC Name3-methylbutanal
Traditional Nameisovaleraldehyde
CAS Registry Number590-86-3
SMILES
CC(C)CC=O
InChI Identifier
InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
InChI KeyYGHRJJRRZDOVPD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-51 °CNot Available
Boiling Point90.00 to 93.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility14 mg/mL at 20 °CNot Available
LogP1.267 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Hepatic encephalopathy
  1. Goldberg EM, Blendis LM, Sandler S: A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. J Chromatogr. 1981 Dec 11;226(2):291-9. [PubMed:7320160 ]
  2. Marshall AW, DeSouza M, Morgan MY: Plasma 3-methylbutanal in man and its relationship to hepatic encephalopathy. Clin Physiol. 1985 Feb;5(1):53-62. [PubMed:4038637 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
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 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Clostridium difficile infection
  1. Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003285
KNApSAcK IDC00048949
Chemspider ID11065
KEGG Compound IDC07329
BioCyc IDCPD-7031
BiGG IDNot Available
Wikipedia LinkIsovaleraldehyde
METLIN IDNot Available
PubChem Compound11552
PDB IDNot Available
ChEBI ID16638
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000485
Good Scents IDrw1023131
References
Synthesis ReferenceRoelen, O. Synthesis of aldehydes and derivatives from olefins, carbon monoxide, and hydrogen. Angew. Chem. (1948), A60 62. CAN 44:46679 AN 1950:46679
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Sampaio OM, Reche RV, Franco DW: Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification. J Agric Food Chem. 2008 Mar 12;56(5):1661-8. doi: 10.1021/jf0726841. Epub 2008 Feb 15. [PubMed:18275147 ]
  3. Tanimoto S, Matsumoto H, Fujii K, Ohdoi R, Sakamoto K, Yamane Y, Miyake M, Shimoda M, Osajima Y: Enzyme inactivation and quality preservation of sake by high-pressure carbonation at a moderate temperature. Biosci Biotechnol Biochem. 2008 Jan;72(1):22-8. Epub 2008 Jan 7. [PubMed:18175918 ]
  4. Whetstine ME, Drake MA, Broadbent JR, McMahon D: Enhanced nutty flavor formation in cheddar cheese made with a malty Lactococcus lactis adjunct culture. J Dairy Sci. 2006 Sep;89(9):3277-84. [PubMed:16899660 ]
  5. Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]