Human Metabolome Database Version 3.5

Showing metabocard for SM(d16:1/24:1(15Z)) (HMDB11694)

Record Information
Version 3.5
Creation Date 2009-02-19 16:38:51 -0700
Update Date 2013-02-08 17:27:10 -0700
HMDB ID HMDB11694
Secondary Accession Numbers None
Metabolite Identification
Common Name SM(d16:1/24:1(15Z))
Description Sphingomyelin (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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. SPH(d16:1/24:1(15Z))
  2. Sphingomyelin (d16:1/24:1(15Z))
Chemical Formula C45H90N2O6P
Average Molecular Weight 786.1797
Monoisotopic Molecular Weight 785.653650134
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 Number Not 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 Key FOULCGVQZYQEQM-DNXGLLHMSA-O
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Sphingolipids
Sub Class Sphingomyelins
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 Parent Sphingomyelins
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.480E-05 g/L ALOGPS
LogP 6.01 ALOGPS
LogP 10.37 ChemAxon
LogS -7.37 ALOGPS
pKa (strongest acidic) 1.87 ChemAxon
pKa (strongest basic) 0.012 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 105.09 A2 ChemAxon
Rotatable Bond Count 41 ChemAxon
Refractivity 243.79 ChemAxon
Polarizability 99.96 ChemAxon
Formal Charge 1 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
15.7 +/- 0.6 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028380
KNApSAcK ID Not Available
Chemspider ID 24768059 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11694 Link_out
Metagene Link HMDB11694 Link_out
METLIN ID Not Available
PubChem Compound 52931202 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not 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 Link_out

Enzymes
Name: Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1
Reactions: Not Available
Gene Name: GBGT1
Uniprot ID: Q8N5D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase
Reactions: Not Available
Gene Name: PIGL
Uniprot ID: Q9Y2B2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase
Reactions: Not Available
Gene Name: SMPD1
Uniprot ID: P17405 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1
Reactions: Not Available
Gene Name: B3GAT1
Uniprot ID: Q9P2W7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
Reactions: Not Available
Gene Name: PIGQ
Uniprot ID: Q9BRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
Reactions: Not Available
Gene Name: PIGA
Uniprot ID: P37287 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit H
Reactions: Not Available
Gene Name: PIGH
Uniprot ID: Q14442 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit P
Reactions: Not Available
Gene Name: PIGP
Uniprot ID: P57054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit C
Reactions: Not Available
Gene Name: PIGC
Uniprot ID: Q92535 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 7
Reactions: Not Available
Gene Name: ENPP7
Uniprot ID: Q6UWV6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 2
Reactions: Not Available
Gene Name: SMPD2
Uniprot ID: O60906 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Proactivator polypeptide
Reactions: Not Available
Gene Name: PSAP
Uniprot ID: P07602 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ganglioside GM2 activator
Reactions: Not Available
Gene Name: GM2A
Uniprot ID: P17900 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1e, membrane-associated
Reactions: Not Available
Gene Name: CD1E
Uniprot ID: P15812 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Epididymal secretory protein E1
Reactions: Not Available
Gene Name: NPC2
Uniprot ID: P61916 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Antigen-presenting glycoprotein CD1d
Reactions: Not Available
Gene Name: CD1D
Uniprot ID: P15813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 1
Reactions: Not Available
Gene Name: PIGM
Uniprot ID: Q9H3S5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class W protein
Reactions: Not Available
Gene Name: PIGW
Uniprot ID: Q7Z7B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class X protein
Reactions: Not Available
Gene Name: PIGX
Uniprot ID: Q8TBF5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 4
Reactions: Not Available
Gene Name: PIGZ
Uniprot ID: Q86VD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3
Reactions: Not Available
Gene Name: PLCD3
Uniprot ID: Q8N3E9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase
Reactions: Not Available
Gene Name: B3GNT5
Uniprot ID: Q9BYG0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 3
Reactions: Not Available
Gene Name: SMPD3
Uniprot ID: Q9NY59 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,3-galactosyltransferase 5
Reactions: Not Available
Gene Name: B3GALT5
Uniprot ID: Q9Y2C3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 3
Reactions: Not Available
Gene Name: PIGB
Uniprot ID: Q92521 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class F protein
Reactions: Not Available
Gene Name: PIGF
Uniprot ID: Q07326 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 2
Reactions: Not Available
Gene Name: PIGG
Uniprot ID: Q5H8A4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 1
Reactions: Not Available
Gene Name: PIGN
Uniprot ID: O95427 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 3
Reactions: Not Available
Gene Name: PIGO
Uniprot ID: Q8TEQ8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI transamidase component PIG-S
Reactions: Not Available
Gene Name: PIGS
Uniprot ID: Q96S52 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI transamidase component PIG-T
Reactions: Not Available
Gene Name: PIGT
Uniprot ID: Q969N2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol glycan anchor biosynthesis class U protein
Reactions: Not Available
Gene Name: PIGU
Uniprot ID: Q9H490 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 2
Reactions: Not Available
Gene Name: PIGV
Uniprot ID: Q9NUD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y
Reactions: Not Available
Gene Name: PIGY
Uniprot ID: Q3MUY2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pleckstrin homology domain-containing family A member 8
Reactions: Not Available
Gene Name: PLEKHA8
Uniprot ID: Q96JA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 4
Reactions: Not Available
Gene Name: SMPD4
Uniprot ID: Q9NXE4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Non-lysosomal glucosylceramidase
Reactions: Not Available
Gene Name: GBA2
Uniprot ID: Q9HCG7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin synthase-related protein 1
Reactions: Not Available
Gene Name: SAMD8
Uniprot ID: Q96LT4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI-anchor transamidase
Reactions: Not Available
Gene Name: PIGK
Uniprot ID: Q92643 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycosylphosphatidylinositol anchor attachment 1 protein
Reactions: Not Available
Gene Name: GPAA1
Uniprot ID: O43292 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein PLEKHA9
Reactions: Not Available
Gene Name: PLEKHA9
Uniprot ID: O95397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycolipid transfer protein domain-containing protein 2
Reactions: Not Available
Gene Name: GLTPD2
Uniprot ID: A6NH11 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative uncharacterized protein PLEKHA8
Reactions: Not Available
Gene Name: PLEKHA8
Uniprot ID: B5MDU3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1a
Reactions: Not Available
Gene Name: CD1A
Uniprot ID: P06126 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycolipid transfer protein domain-containing protein 1
Reactions: Not Available
Gene Name: GLTPD1
Uniprot ID: Q5TA50 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1c
Reactions: Not Available
Gene Name: CD1C
Uniprot ID: P29017 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipopolysaccharide-binding protein
Reactions: Not Available
Gene Name: LBP
Uniprot ID: P18428 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative uncharacterized protein DKFZp434L0435
Reactions: Not Available
Gene Name: DKFZp434L0435
Uniprot ID: Q9UFH6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1b
Reactions: Not Available
Gene Name: CD1B
Uniprot ID: P29016 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycolipid transfer protein
Reactions: Not Available
Gene Name: GLTP
Uniprot ID: Q9NZD2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA