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Showing metabocard for 4-Methylpentanal (HMDB0001318)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version4.0
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 through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 17a-hydroxypregnenolone and 4-methylpentanal can be biosynthesized from 17a,20a-dihydroxycholesterol; which is catalyzed by the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In humans, 4-methylpentanal is involved in the metabolic disorder called the apparent mineralocorticoid excess syndrome pathway.
Structure
Data?1582752191
MOLSDFPDBSMILESInChI
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:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-bca9e68c6009fa9d2c06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-4900000000-fb4261b2e4f6e3a98960Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9600000000-55f36997fe423e576d10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-f50d789cecc6faada43dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-8d50a1d5a37313cc062aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-c2f12b63b2a31cb18f8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-16c6cae0f1217d0ae1a5Spectrum
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
FoodDB 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 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

Enzyme Details
1. Cholesterol side-chain cleavage enzyme, mitochondrial
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