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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-16 03:42:46 UTC
Update Date2022-11-30 20:07:09 UTC
HMDB IDHMDB0290414
Secondary Accession NumbersNone
Metabolite Identification
Common NameSM(d17:2(4E,8Z)/6 keto-PGF1alpha)
DescriptionSM(d17:2(4E,8Z)/6 keto-PGF1alpha) is a type of oxidized sphingolipid found in animal cell membranes. It usually consists of phosphorylcholine and ceramide. SM(d17:2(4E,8Z)/6 keto-PGF1alpha) consists of a sphingosine backbone and a 6-Keto-prostaglandin F1alpha chain. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SM 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 localize 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
ValueSource
SM(D17:2(4E,8Z)/6 keto-PGF1a)Generator
SM(D17:2(4E,8Z)/6 keto-PGF1α)Generator
Chemical FormulaC42H77N2O10P
Average Molecular Weight801.056
Monoisotopic Molecular Weight800.531583685
IUPAC Name(2-{[(2S,3R,4E,8Z)-2-{7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanamido}-3-hydroxyheptadeca-4,8-dien-1-yl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2S,3R,4E,8Z)-2-{7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanamido}-3-hydroxyheptadeca-4,8-dien-1-yl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCC(=O)C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC
InChI Identifier
InChI=1S/C42H77N2O10P/c1-6-8-10-11-12-13-14-15-16-17-18-20-25-39(47)38(33-54-55(51,52)53-30-29-44(3,4)5)43-42(50)26-22-21-24-35(46)31-37-36(40(48)32-41(37)49)28-27-34(45)23-19-9-7-2/h15-16,20,25,27-28,34,36-41,45,47-49H,6-14,17-19,21-24,26,29-33H2,1-5H3,(H-,43,50,51,52)/b16-15-,25-20+,28-27+/t34-,36+,37+,38-,39+,40+,41-/m0/s1
InChI KeyMFSBLDQNWUHGEN-KDIYXBIYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.39ALOGPS
logP1.71ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area185.68 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity233.37 m³·mol⁻¹ChemAxon
Polarizability92.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+289.72732859911
AllCCS[M+H-H2O]+289.7532859911
AllCCS[M+Na]+289.6532859911
AllCCS[M+NH4]+289.67232859911
AllCCS[M-H]-283.88832859911
AllCCS[M+Na-2H]-288.36832859911
AllCCS[M+HCOO]-293.30932859911
DeepCCS[M+H]+286.27130932474
DeepCCS[M-H]-284.54830932474
DeepCCS[M-2H]-318.76530932474
DeepCCS[M+Na]+292.630932474

Predicted Kovats Retention Indices

Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available