Record Information
Version3.6
Creation Date2009-02-19 23:38:51 UTC
Update Date2013-02-09 00:27:10 UTC
HMDB IDHMDB11694
Secondary Accession NumbersNone
Metabolite Identification
Common NameSM(d16:1/24:1(15Z))
DescriptionSphingomyelin (d16:1/24:1(15Z)) or SM(d16:1/24:1(15Z)) is a sphingomyelin. Sphingomyelin (SM or SPH) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase.
Structure
Thumb
Synonyms
  1. SPH(d16:1/24:1(15Z))
  2. Sphingomyelin (d16:1/24:1(15Z))
Chemical FormulaC45H90N2O6P
Average Molecular Weight786.1797
Monoisotopic Molecular Weight785.653650134
IUPAC Name{[(2S,3R,4E)-3-hydroxy-2-[(15Z)-tetracos-15-enamido]hexadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid
Traditional IUPAC Name[(2S,3R,4E)-3-hydroxy-2-[(15Z)-tetracos-15-enamido]hexadec-4-en-1-yl]oxy(2-(trimethylaminio)ethoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCC\C=C\[C@@]([H])(O)[C@]([H])(COP(O)(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C45H89N2O6P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(49)46-43(42-53-54(50,51)52-41-40-47(3,4)5)44(48)38-36-34-32-30-28-17-15-13-11-9-7-2/h19-20,36,38,43-44,48H,6-18,21-35,37,39-42H2,1-5H3,(H-,46,49,50,51)/p+1/b20-19-,38-36+/t43-,44+/m0/s1
InChI KeyFOULCGVQZYQEQM-DNXGLLHMSA-O
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSphingolipids
Sub ClassSphingomyelins
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxamide Group
  • Choline
  • N Acyl Amine
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphocholine
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Quaternary Ammonium Salt
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentSphingomyelins
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
water solubility3.480E-05 g/LALOGPS
logP6.01ALOGPS
logP10.37ChemAxon
logS-7.4ALOGPS
pKa (strongest acidic)1.87ChemAxon
pKa (strongest basic)0.012ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area105.09ChemAxon
rotatable bond count41ChemAxon
refractivity243.79ChemAxon
polarizability99.96ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified15.7 +/- 0.6 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028380
KNApSAcK IDNot Available
Chemspider ID24768059
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11694
Metagene LinkHMDB11694
METLIN IDNot Available
PubChem Compound52931202
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ding J, Sorensen CM, Jaitly N, Jiang H, Orton DJ, Monroe ME, Moore RJ, Smith RD, Metz TO: Application of the accurate mass and time tag approach in studies of the human blood lipidome. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Aug 15;871(2):243-52. Epub 2008 May 7. Pubmed: 18502191

Enzymes

Gene Name:
SMPD1
Uniprot ID:
P17405
Gene Name:
SMPD2
Uniprot ID:
O60906
Gene Name:
PSAP
Uniprot ID:
P07602
Gene Name:
GM2A
Uniprot ID:
P17900
Gene Name:
NPC2
Uniprot ID:
P61916
Gene Name:
CD1D
Uniprot ID:
P15813
Gene Name:
PIGM
Uniprot ID:
Q9H3S5
Gene Name:
PIGZ
Uniprot ID:
Q86VD9
Gene Name:
SMPD3
Uniprot ID:
Q9NY59
Gene Name:
B3GALT5
Uniprot ID:
Q9Y2C3
Gene Name:
PIGB
Uniprot ID:
Q92521
Gene Name:
PIGS
Uniprot ID:
Q96S52
Gene Name:
PIGT
Uniprot ID:
Q969N2
Gene Name:
PIGV
Uniprot ID:
Q9NUD9
Gene Name:
SMPD4
Uniprot ID:
Q9NXE4
Gene Name:
GBA2
Uniprot ID:
Q9HCG7
Gene Name:
PIGK
Uniprot ID:
Q92643
Gene Name:
PLEKHA9
Uniprot ID:
O95397
Gene Name:
PLEKHA8
Uniprot ID:
B5MDU3
Gene Name:
CD1A
Uniprot ID:
P06126
Gene Name:
CD1C
Uniprot ID:
P29017
Gene Name:
LBP
Uniprot ID:
P18428
Gene Name:
DKFZp434L0435
Uniprot ID:
Q9UFH6
Gene Name:
CD1B
Uniprot ID:
P29016
Gene Name:
GLTP
Uniprot ID:
Q9NZD2