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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:20:59 UTC
Update Date2019-07-23 06:22:57 UTC
HMDB IDHMDB0037105
Secondary Accession Numbers
  • HMDB37105
Metabolite Identification
Common NameArmillaramide
DescriptionArmillaramide belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine. Armillaramide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862977
Synonyms
ValueSource
(2S,3S,4R)-2-Hexadecanoylamino-octadecane-1,3,4-triolHMDB
N-(1,3,4-Trihydroxyoctadecan-2-yl)hexadecanimidateGenerator
ArmillaramideMeSH
Chemical FormulaC34H69NO4
Average Molecular Weight555.916
Monoisotopic Molecular Weight555.522659701
IUPAC NameN-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanamide
Traditional NameN-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C(O)CCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C34H69NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(38)35-31(30-36)34(39)32(37)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h31-32,34,36-37,39H,3-30H2,1-2H3,(H,35,38)
InChI KeyIVBULNXGVIHEKN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentPhytoceramides
Alternative Parents
Substituents
  • N-acyl-4-hydroxysphinganine
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Polyol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00013 g/LALOGPS
logP8.76ALOGPS
logP10ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)13.26ChemAxon
pKa (Strongest Basic)0.029ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity166.17 m³·mol⁻¹ChemAxon
Polarizability74.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-2276985000-a84149f527555235e46bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-0025090000-fbaa290f8d7609218d60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gj-6192010000-6b251d870dbc2b4e41cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-6792000000-1a28fbbbb9a61abc648eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0052090000-bfe226fb5d99bd01ed83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kaa-1091010000-73a742135fc960b6db47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9170000000-7187875d2a3672092ee2Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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
FooDB IDFDB016096
KNApSAcK IDNot Available
Chemspider ID7983535
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9807776
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  2. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Pruett ST, Bushnev A, Hagedorn K, Adiga M, Haynes CA, Sullards MC, Liotta DC, Merrill AH Jr: Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols. J Lipid Res. 2008 Aug;49(8):1621-39. doi: 10.1194/jlr.R800012-JLR200. Epub 2008 May 21. [PubMed:18499644 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Hannun YA, Obeid LM: Ceramide: an intracellular signal for apoptosis. Trends Biochem Sci. 1995 Feb;20(2):73-7. [PubMed:7701566 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  10. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.