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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:11 UTC
HMDB IDHMDB0001318
Secondary Accession Numbers
  • HMDB01318
Metabolite Identification
Common Name4-Methylpentanal
Description4-Methylpentanal, also known as isohexanal or isocaproaldehyde, 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. 4-Methylpentanal is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 4-methylpentanal participates in a number of enzymatic reactions. In particular, pregnenolone and 4-methylpentanal can be biosynthesized from 20a,22b-dihydroxycholesterol; which is mediated by the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 17a-hydroxypregnenolone and 4-methylpentanal can be biosynthesized from 17a,20a-dihydroxycholesterol through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In humans, 4-methylpentanal is involved in the metabolic disorder called the 11-beta-hydroxylase deficiency (cyp11b1) pathway. Outside of the human body, 4-Methylpentanal has been detected, but not quantified in, milk (cow). This could make 4-methylpentanal a potential biomarker for the consumption of these foods.
Structure
Data?1582752191
Synonyms
ValueSource
4-Methyl valeraldehydeChEBI
IsocaproaldehydeChEBI
IsohexanalChEBI
4-Methyl-valeraldehydeHMDB
4-MethylvaleraldehydeHMDB
Isocaproaldehyde: 4-methyl-pentanalHMDB
IsohexanaHMDB
Chemical FormulaC6H12O
Average Molecular Weight100.1589
Monoisotopic Molecular Weight100.088815006
IUPAC Name4-methylpentanal
Traditional Nameisocaproaldehyde
CAS Registry Number1119-16-0
SMILES
CC(C)CCC=O
InChI Identifier
InChI=1S/C6H12O/c1-6(2)4-3-5-7/h5-6H,3-4H2,1-2H3
InChI KeyJGEGJYXHCFUMJF-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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.8 g/LALOGPS
logP1.92ALOGPS
logP1.49ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)15.45ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.1 m³·mol⁻¹ChemAxon
Polarizability12.14 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]+120.51831661259
DarkChem[M-H]-116.31631661259
AllCCS[M+H]+124.50232859911
AllCCS[M-H]-129.53832859911
DeepCCS[M+H]+127.66830932474
DeepCCS[M-H]-125.62930932474
DeepCCS[M-2H]-161.24830932474
DeepCCS[M+Na]+135.93430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-MethylpentanalCC(C)CCC=O1033.4Standard polar33892256
4-MethylpentanalCC(C)CCC=O733.8Standard non polar33892256
4-MethylpentanalCC(C)CCC=O770.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Methylpentanal,1TMS,isomer #1CC(C)CC=CO[Si](C)(C)C977.6Semi standard non polar33892256
4-Methylpentanal,1TMS,isomer #1CC(C)CC=CO[Si](C)(C)C940.0Standard non polar33892256
4-Methylpentanal,1TMS,isomer #1CC(C)CC=CO[Si](C)(C)C1011.0Standard polar33892256
4-Methylpentanal,1TBDMS,isomer #1CC(C)CC=CO[Si](C)(C)C(C)(C)C1195.3Semi standard non polar33892256
4-Methylpentanal,1TBDMS,isomer #1CC(C)CC=CO[Si](C)(C)C(C)(C)C1166.2Standard non polar33892256
4-Methylpentanal,1TBDMS,isomer #1CC(C)CC=CO[Si](C)(C)C(C)(C)C1208.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylpentanal GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-bca9e68c6009fa9d2c062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylpentanal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylpentanal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 10V, Positive-QTOFsplash10-0udi-4900000000-fb4261b2e4f6e3a989602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 20V, Positive-QTOFsplash10-0ue9-9600000000-55f36997fe423e576d102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 40V, Positive-QTOFsplash10-0a4l-9000000000-f50d789cecc6faada43d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 10V, Negative-QTOFsplash10-0002-9000000000-8d50a1d5a37313cc062a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 20V, Negative-QTOFsplash10-0002-9000000000-c2f12b63b2a31cb18f8f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 40V, Negative-QTOFsplash10-0006-9000000000-16c6cae0f1217d0ae1a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 10V, Positive-QTOFsplash10-0a5c-9000000000-9fe8fc0a03ea11fad1f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 20V, Positive-QTOFsplash10-052f-9000000000-a1773bff919aabed87de2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 40V, Positive-QTOFsplash10-05o3-9000000000-dee2ad740e4bdcb047132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 10V, Negative-QTOFsplash10-0002-9000000000-658fe53778817eb823012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 20V, Negative-QTOFsplash10-000t-9000000000-e2fa6386c12bc1f2f5742021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylpentanal 40V, Negative-QTOFsplash10-0006-9000000000-ef27d33d100c1fd00b132021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022551
KNApSAcK IDNot Available
Chemspider ID126
KEGG Compound IDC02373
BioCyc IDNot Available
BiGG ID39716
Wikipedia LinkNot Available
METLIN ID6155
PubChem Compound129
PDB IDNot Available
ChEBI ID17998
Food Biomarker OntologyNot Available
VMH ID4MPTNL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMatsuura K; Deyashiki Y; Bunai Y; Ohya I; Hara A Aldose reductase is a major reductase for isocaproaldehyde, a product of side-chain cleavage of cholesterol, in human and animal adrenal glands. Archives of biochemistry and biophysics (1996), 328(2), 265-71.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
Reactions
Cholesterol + reduced adrenal ferredoxin + Oxygen → Pregnenolone + 4-Methylpentanal + oxidized adrenal ferredoxin + Waterdetails
20a,22b-Dihydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 4-Methylpentanal + Pregnenolone + Water + Oxidized adrenal ferredoxindetails
17a,20a-Dihydroxycholesterol + Oxygen + Hydrogen Ion + Reduced adrenal ferredoxin → 17a-Hydroxypregnenolone + 4-Methylpentanal + Water + Oxidized adrenal ferredoxindetails