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Showing NP-Card for Iso-Valeraldehyde (NP0000658)

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Record Information
Version1.0
Created at2007-05-23 11:08:59 UTC
Updated at2021-08-19 23:58:18 UTC
NP-MRD IDNP0000658
Secondary Accession NumbersNone
Natural Product Identification
Common NameIso-Valeraldehyde
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 NP0000658 (Iso-Valeraldehyde)


  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 NP0000658 (Iso-Valeraldehyde)

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 NP0000658 (Iso-Valeraldehyde)


  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>
NP0000658

> <DATABASE_NAME>
NP-MRD

> <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 NP0000658 (Iso-Valeraldehyde)

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 NP0000658 (Iso-Valeraldehyde)

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 NP0000658 (Iso-Valeraldehyde)

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 NP0000658 (Iso-Valeraldehyde)

CC(C)CC=O
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INCHI for NP0000658 (Iso-Valeraldehyde)

InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
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View in JSmol
Synonyms
ValueSource
3-MethylbutyraldehydeChEBI
beta-MethylbutanalChEBI
Iso-C4H9CHOChEBI
Isoamyl aldehydeChEBI
IsopentaldehydeChEBI
IsovaleralChEBI
IsovalerylaldehydeChEBI
b-MethylbutanalGenerator
Β-methylbutanalGenerator
2-Methylbutanal-4HMDB
3-Methyl-1-butanalHMDB
3-Methyl-butanalHMDB
3-Methyl-butyraldehydeHMDB
3-Methylbutan-1-alHMDB
3-MethylbutanalHMDB
IsoamylaldehydeHMDB
IsopentanalHMDB
Isovaleric aldehydeHMDB
Methyl butanalHMDB
Iso-valeraldehydeHMDB
IsovaleraldehydeChEBI
Chemical FormulaC5H10O
Average Mass86.1323 Da
Monoisotopic Mass86.07316 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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 NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Aesculus hippocastanumLOTUS Database
Allium ampeloprasumLOTUS Database
Anethum foeniculumPlant
Apium graveolens var. dulceFooDB
    • Fredy A. Van Wassenhove, Patrick J. Dirinck, Niceas M. Schamp, and Georges A. Vulsteke. Effect of...
Apium graveolens var. rapaceumFooDB
    • Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Asarum canadenseLOTUS Database
Aster scaberLOTUS Database
Brassica oleracea var. gongylodesFooDB
Cannabis sativaCannabisDB
      Not Available
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Citrullus vulgarisKNApSAcK Database
Coffea arabicaKNApSAcK Database
Coffea arabica L.Plant
Cymbopogon citratusFooDB
Daphne papyraceaLOTUS Database
Daucus carota ssp. sativusFooDB
Eucalyptus brassianaLOTUS Database
Eucalyptus degluptaLOTUS Database
Eucalyptus delegatensisLOTUS Database
Eucalyptus globulusLOTUS Database
Eucalyptus nitensLOTUS Database
Eucalyptus pulverulentaLOTUS Database
Foeniculum vulgareKNApSAcK Database
Gossypium hirsutumLOTUS Database
Gyromitra esculentaLOTUS Database
Kunzea salinaLOTUS Database
Laurus nobilis L.FooDB
Malus pumilaFooDB
Mangifera indicaKNApSAcK Database
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Musa paradisiacaLOTUS Database
Ocimum basilicumFooDB
Olea europaeaKNApSAcK Database
Pimenta dioicaFooDB
Prunus aviumKNApSAcK Database
Solanum lycopersicum var. lycopersicumFooDB
Solanum tuberosumFooDB
Theobroma cacaoLOTUS Database
Tuber borchii-
Tuber brumale-
Tuber excavatum-
Tuber indicum-
Tuber magnatum-
Tuber melanosporum-
Tuber mesentericum-
Tuber oligospermum-
Tuber panniferum-
Tuber rufum-
Tuber uncinatum-
Zea mays L.FooDB
    • Carlos Macku, and Takayuki Shibamoto. Headspace volatile compounds formed from heated corn oil an...
Zingiber officinaleKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Exhaled breath)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateLiquid
Experimental 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
Predicted Properties
PropertyValueSource
Water Solubility17 g/LALOGPS
logP1.29ALOGPS
logP1.05ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)18.56ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.49 m³·mol⁻¹ChemAxon
Polarizability10.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006478
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1023131
References
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. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. doi: 10.1017/s0022029902005782. [PubMed:12463694 ]