Record Information
Version3.6
Creation Date2010-03-24 16:57:20 UTC
Update Date2013-02-09 00:30:17 UTC
HMDB IDHMDB13462
Secondary Accession NumbersNone
Metabolite Identification
Common NameSM(d18:0/14:1(9Z)(OH))
DescriptionSphingomyelin (d18:0/14:1(9Z)(OH)) or SM(d18:0/14:1(9Z)(OH)) 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. C14:1-OH Sphingomyelin
  2. N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine
Chemical FormulaC37H73N2O7P
Average Molecular Weight688.9585
Monoisotopic Molecular Weight688.515539212
IUPAC Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxytetradec-9-enamido]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxytetradec-9-enamido]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCC
InChI Identifier
InChI=1S/C37H73N2O7P/c1-6-8-10-12-14-16-17-18-19-21-23-25-27-29-36(41)35(33-46-47(43,44)45-31-30-39(3,4)5)38-37(42)32-34(40)28-26-24-22-20-15-13-11-9-7-2/h13,15,27,29,34-36,40-41H,6-12,14,16-26,28,30-33H2,1-5H3,(H-,38,42,43,44)/b15-13-,29-27+/t34?,35-,36+/m0/s1
InChI KeyZNHNJXWKKQKMBU-POWUNZFVSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSphingolipids
Sub ClassSphingomyelins
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • 1,3 Aminoalcohol
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxamide Group
  • Ceramide
  • 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 solubility5.960E-05 g/LALOGPS
logP3.91ALOGPS
logP4.49ChemAxon
logS-7.1ALOGPS
pKa (strongest acidic)1.87ChemAxon
pKa (strongest basic)-1.2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area128.15ChemAxon
rotatable bond count33ChemAxon
refractivity207.37ChemAxon
polarizability82.81ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified0.028 +/- 0.004 uMAdult (>18 years old)Not SpecifiedNormal
UrineDetected and Quantified0.0028 (0.0008-0.0049) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
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 IDFDB029462
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00550
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSphingomyelin
NuGOwiki LinkHMDB13462
Metagene LinkHMDB13462
METLIN IDNot Available
PubChem Compound53481777
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 50 proteins. There are 52 proteins in total.

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

Only showing the first 50 proteins. There are 52 proteins in total.