Showing metabocard for SM(d18:0/18:1(9Z)) (BMDB0012089)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:32:05 UTC
Update Date2020-06-04 19:56:12 UTC
MCDB ID BMDB0012089
Secondary Accession Numbers
  • BMDB12089
Metabolite Identification
Common NameSM(d18:0/18:1(9Z))
DescriptionSM(D18:0/18:1(9Z)), also known as C18:1DH sphingomyelin, belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. Thus, SM(D18:0/18:1(9Z)) is considered to be a phosphosphingolipid lipid molecule. SM(D18:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SphingomyelinMetBuilder
N-(9Z-Octadecenoyl)-1-phosphocholine-sphinganineMetBuilder
Sphingomyelin(D18:0/18:1(9Z))MetBuilder
N-(9Z-Octadecenoyl)-1-phosphocholine-dihydrosphingosineMetBuilder
N-(9Z-Octadecenoyl)-1-phosphocholine-D-erythro-sphinganineMetBuilder
Chemical FormulaC41H83N2O6P
Average Molecular Weight731.097
Monoisotopic Molecular Weight730.598875399
IUPAC Name(2-{[(2S)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadecyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadecyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,39-40,44H,6-19,22-38H2,1-5H3,(H-,42,45,46,47)/b21-20-/t39-,40?/m0/s1
InChI KeyXYLWKHKCYHMVMA-RUMIPHAVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassPhosphosphingolipids
Direct ParentPhosphosphingolipids
Alternative Parents
Substituents
  • Sphingoid-1-phosphate or derivatives
  • Phosphocholine
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Fatty amide
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.41ALOGPS
logP7.71ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.92 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity223.3 m³·mol⁻¹ChemAxon
Polarizability92.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001s-6030190400-17b9b53a12286d3eaba22019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2080191000-a473081811027a912f972019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-6090012000-25e7d04950bfc0c255592019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0010004900-ee6bea26269be07783892019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1051039200-806fdf085b442284c2502019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9182020000-e2a17725e2416df31a522019-02-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified1.04 +/- 0.02 uM details
Detected and Quantified1.09 +/- 0.03 uM details
Detected and Quantified1.19 +/- 0.02 uM details
Detected and Quantified1.13 +/- 0.01 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.