Showing metabocard for Pristanal (BMDB0001958)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:08 UTC
Update Date2020-05-21 16:28:37 UTC
BMDB IDBMDB0001958
Secondary Accession Numbers
  • BMDB01958
Metabolite Identification
Common NamePristanal
DescriptionPristanal belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, pristanal is considered to be an isoprenoid lipid molecule. Pristanal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Pristanal can be converted into pristanic acid through the action of the enzyme fatty aldehyde dehydrogenase. In cattle, pristanal is involved in the metabolic pathway called the phytanic Acid peroxisomal oxidation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,6,10,14-TetramethylpentadecanalChEBI
(2R)-PristanalHMDB
(2R,6R,10R)-2,6,10,14-TetramethylpentadecanalHMDB
(2S)-PristanalHMDB
(2S,6R,10R)-2,6,10,14-TetramethylpentadecanalHMDB
2(R)-PristanalHMDB
2(S)-PristanalHMDB
2RPR-Al (2R,6R,10R,14)-tetramethylpentadecanalHMDB
2SPR-AlHMDB
Chemical FormulaC19H38O
Average Molecular Weight282.5044
Monoisotopic Molecular Weight282.292265838
IUPAC Name2,6,10,14-tetramethylpentadecanal
Traditional Namepristanal
CAS Registry Number105373-75-9
SMILES
CC(C)CCCC(C)CCCC(C)CCCC(C)C=O
InChI Identifier
InChI=1S/C19H38O/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20/h15-19H,6-14H2,1-5H3
InChI KeyIZJRIIWUSIGEAJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Fatty aldehyde
  • Fatty acyl
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.79ALOGPS
logP7.06ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)16.07ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.78 m³·mol⁻¹ChemAxon
Polarizability38.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-067l-6940000000-92eea11a4ee17a868449View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-e6bb3c75007615689c57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ayi-9760000000-b0b1ff6d42edf755a92fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9310000000-97899f565140e079d0ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3c966a223d603742f355View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-8eda93a79a842a9a37caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9240000000-5e254cf1636165308b96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-b6ba81f0eb58de0f8042View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-10382921dc6d5ef46e72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kur-2590000000-2f74d39f42cf441c367eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3290000000-c34f796fefe80e714371View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08mr-9610000000-7a9564f8dcd28f76b828View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9000000000-69d4c995218aa5f3e55bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Peroxisome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001958
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022765
KNApSAcK IDNot Available
Chemspider ID13628282
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2364547
Wikipedia LinkNot Available
METLIN ID6402
PubChem Compound14671060
PDB IDNot Available
ChEBI ID49189
References
Synthesis ReferenceJung, Michael E.; Liu, Ching Yang. Efficient synthesis of a head-to-head isoprenoid geochemical biomarker from phytol. Journal of Organic Chemistry (1986), 51(26), 5446-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-hydroxyacyl-CoA lyase 2
General function:
Amino acid transport and metabolism
Specific function:
Endoplasmic reticulum 2-OH acyl-CoA lyase involved in the cleavage (C1 removal) reaction in the fatty acid alpha-oxydation in a thiamine pyrophosphate (TPP)-dependent manner. Involved in the phytosphingosine degradation pathway.
Gene Name:
ILVBL
Uniprot ID:
A6QQT9
Molecular weight:
68110.0
Reactions
2-Hydroxyphytanoyl-CoA → Pristanal + Formyl-CoAdetails
Enzyme Details
2. Aldehyde dehydrogenase family 3 member B1
General function:
Energy production and conversion
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. Can use both NADP(+) and NAD(+) as electron acceptor. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
Q1JPA0
Molecular weight:
51800.0
Reactions
Pristanal + NAD + Water → Pristanic acid + NADHdetails