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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:55 UTC
HMDB IDHMDB01551
Secondary Accession NumbersNone
Metabolite Identification
Common NamePalmitaldehyde
DescriptionPalmitaldehyde is an intermediate in the metabolism of Glycosphingolipid. It is a substrate for Sphingosine-1-phosphate lyase 1.
Structure
Thumb
Synonyms
ValueSource
Palmitoyl aldehydeHMDB
Chemical FormulaC16H32O
Average Molecular Weight240.4247
Monoisotopic Molecular Weight240.245315646
IUPAC Namehexadecanal
Traditional Namepalmitoyl
CAS Registry Number629-80-1
SMILES
CCCCCCCCCCCCCCCC=O
InChI Identifier
InChI=1S/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h16H,2-15H2,1H3
InChI KeyInChIKey=NIOYUNMRJMEDGI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty aldehydes
Direct ParentFatty aldehydes
Alternative Parents
Substituents
  • Fatty aldehyde
  • Alpha-hydrogen aldehyde
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Glycosphingolipid metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point35 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.88e-05 mg/mLALOGPS
logP7.18ALOGPS
logP6.1ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)15.56ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity76.16 m3·mol-1ChemAxon
Polarizability33.39 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-88e54e24615fc9448538View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9870000000-3679ce8f10212501edf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-5eda4a41605088fce3d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-316d73b64e71af600885View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1090000000-a5b8781e35a4c0e0ef85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9110000000-602590712b86442e2155View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fabry diseaseSMP00525Not Available
Gaucher DiseaseSMP00349Not Available
Globoid Cell LeukodystrophySMP00348Not Available
Krabbe diseaseSMP00526Not Available
Metachromatic Leukodystrophy (MLD)SMP00347Not Available
Sphingolipid MetabolismSMP00034map00500
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03381
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003048
KNApSAcK IDC00007542
Chemspider ID959
KEGG Compound IDC00517
BioCyc IDPALMITALDEHYDE
BiGG ID35223
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01551
Metagene LinkHMDB01551
METLIN ID6317
PubChem Compound984
PDB IDNot Available
ChEBI ID17600
References
Synthesis ReferenceVignais, Pierce V.; Zabin, Irving. Formation of palmitaldehyde in rat brain. Biochem. Lipids Proc. 5th Intern. Conf. Vienna (1960), Volume Date 1958, 78-84.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine. Elevates stress-induced ceramide production and apoptosis.
Gene Name:
SGPL1
Uniprot ID:
O95470
Molecular weight:
63523.265
Reactions
Sphinganine 1-phosphate → O-Phosphoethanolamine + Palmitaldehydedetails
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Photoreceptor required for image-forming vision at low light intensity. Required for photoreceptor cell viability after birth. Light-induced isomerization of 11-cis to all-trans retinal triggers a conformational change leading to G-protein activation and release of all-trans retinal
Gene Name:
RHO
Uniprot ID:
P08100
Molecular weight:
38892.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General function:
Involved in acyl-CoA binding
Specific function:
Binds medium- and long-chain acyl-CoA esters with very high affinity and may function as an intracellular carrier of acyl-CoA esters. It is also able to displace diazepam from the benzodiazepine (BZD) recognition site located on the GABA type A receptor. It is therefore possible that this protein also acts as a neuropeptide to modulate the action of the GABA receptor
Gene Name:
DBI
Uniprot ID:
P07108
Molecular weight:
10044.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reduction of saturated fatty acyl-CoA with chain length C16 or C18 to fatty alcohols.
Gene Name:
FAR1
Uniprot ID:
Q8WVX9
Molecular weight:
59356.25
Reactions
Palmitaldehyde + Coenzyme A + NADP → hexadecanoyl-CoA + NADPHdetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reduction of fatty acyl-CoA to fatty alcohols. The preferred substrates are C16, C18, C18:1 and C18:2 but low activity can be observed with C10-C14 substrates.
Gene Name:
FAR2
Uniprot ID:
Q96K12
Molecular weight:
59437.92
Reactions
Palmitaldehyde + Coenzyme A + NADP → hexadecanoyl-CoA + NADPHdetails