Showing metabocard for 4-Methylpentanal (BMDB0001318)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:04 UTC
Update Date2020-04-22 15:07:37 UTC
BMDB IDBMDB0001318
Secondary Accession Numbers
  • BMDB01318
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 possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Methylpentanal participates in a number of enzymatic reactions, within cattle. In particular, Pregnenolone and 4-methylpentanal can be biosynthesized from 20a,22b-dihydroxycholesterol; which is catalyzed 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 cattle, 4-methylpentanal is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001318
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
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 References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Enzymes

Enzyme Details
1. Cholesterol side-chain cleavage enzyme, mitochondrial
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the side-chain hydroxylation and cleavage of cholesterol to pregnenolone, the precursor of most steroid hormones (PubMed:11412116). Catalyzes three sequential oxidation reactions of cholesterol, namely the hydroxylation at C22 followed with the hydroxylation at C20 to yield 20R,22R-hydroxycholesterol that is further cleaved between C20 and C22 to yield the C21-steroid pregnenolone and 4-methylpentanal (PubMed:11412116). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11412116).
Gene Name:
CYP11A1
Uniprot ID:
P00189
Molecular weight:
60333.0