Showing metabocard for Dihydroceramide (BMDB0006752)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:31 UTC
Update Date2020-05-21 16:28:59 UTC
BMDB IDBMDB0006752
Secondary Accession Numbers
  • BMDB06752
Metabolite Identification
Common NameDihydroceramide
DescriptionDihydroceramide, also known as N-acylsphinganine, belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl). Dihydroceramide is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroceramide exists in all eukaryotes, ranging from yeast to humans. Within cattle, dihydroceramide participates in a number of enzymatic reactions. In particular, dihydroceramide can be converted into ceramide (D18:1/18:0) through the action of the enzyme sphingolipid delta(4)-desaturase/c4-hydroxylase DES2. In addition, dihydroceramide can be converted into sphinganine through its interaction with the enzyme alkaline ceramidase 3. In cattle, dihydroceramide is involved in the metabolic pathway called the sphingolipid metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-AcylsphinganineHMDB
N-[(2S,3R)-1,3-Dihydroxyoctadecan-2-yl]formamideHMDB
Chemical FormulaC19H39NO3
Average Molecular Weight329.5179
Monoisotopic Molecular Weight329.292994119
IUPAC NameN-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]formamide
Traditional NameN-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]formamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC=O
InChI Identifier
InChI=1S/C19H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(23)18(16-21)20-17-22/h17-19,21,23H,2-16H2,1H3,(H,20,22)/t18-,19+/m0/s1
InChI KeyXSDVOEIEBUGRQX-RBUKOAKNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentSecondary carboxylic acid amides
Alternative Parents
Substituents
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.68ALOGPS
logP4.54ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.11ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity95.88 m³·mol⁻¹ChemAxon
Polarizability42.49 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, Positivesplash10-000l-9761000000-49c3e7ef71f565d78a20View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2490200000-ce76ab5497791fd51fe6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0il0-0049000000-5dfda3f1388f3abf30f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ec-5396000000-450d57020d5338301d11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-4970000000-e72e84aaddbd263f496cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2059000000-0a230b14683a27fa8d7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r7-9074000000-7b5c74746bfdd2286b68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9010000000-dbf19cabd1b95226fa8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-9df513b3b35b71e70579View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0059000000-57e37cdd69b1cdd2833bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02u0-0094000000-e3d26a0a236ec35d2a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-ba73a2cbcbb544cfeda7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0019000000-2e93209c7f8eb50ded10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-1096000000-3456b2e34beb0df0f515View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006752
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024056
KNApSAcK IDNot Available
Chemspider ID21436314
KEGG Compound IDC12126
BioCyc IDNot Available
BiGG ID2263543
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16755624
PDB IDNot Available
ChEBI ID31488
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Sphingolipid delta(4)-desaturase/C4-monooxygenase DES2
General function:
Not Available
Specific function:
Bifunctional enzyme which acts as both a sphingolipid delta(4)-desaturase and a sphingolipid C4-monooxygenase.
Gene Name:
DEGS2
Uniprot ID:
Q0II71
Molecular weight:
37319.0
Reactions
Dihydroceramide → Ceramide (d18:1/18:0)details
Enzyme Details
2. Alkaline ceramidase
General function:
Not Available
Specific function:
Hydrolyzes the sphingolipid ceramide into sphingosine and free fatty acid.
Gene Name:
ACER3
Uniprot ID:
A7MBH7
Molecular weight:
31491.0
Reactions
Dihydroceramide → Sphinganinedetails