Showing chemical card for SM(d19:0/20:3(6,8,11)-OH(5)) (CFc000270173)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:11:13 UTC

Chemfont ID

CFc000270173

Molecule Identification

Common Name

SM(d19:0/20:3(6,8,11)-OH(5))

Definition

SM(d19:0/20:3(6,8,11)-OH(5)) is a type of oxidized sphingolipid found in animal cell membranes. It usually consists of phosphorylcholine and ceramide. SM(d19:0/20:3(6,8,11)-OH(5)) consists of a sphingosine backbone and a 5-hydroxyeicosatetrienoyl 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

MOL SDF PDB SMILES InChI

SMILES for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCC(O)\C=C\C=C\C\C=C\CCCCCCCC)[C@H](O)CCCCCCCCCCCCCCCC

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INCHI for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

InChI=1S/C44H85N2O7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-36-43(48)42(40-53-54(50,51)52-39-38-46(3,4)5)45-44(49)37-33-35-41(47)34-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,27,29,31,34,41-43,47-48H,6-20,22,24-26,28,30,32-33,35-40H2,1-5H3,(H-,45,49,50,51)/b23-21+,29-27+,34-31+/t41?,42-,43+/m0/s1

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Structure for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

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3D Structure for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

Synonyms

Not Available

Chemical Formula

C₄₄H₈₅N₂O₇P

Average Molecular Weight

785.145

Monoisotopic Molecular Weight

784.609440083

IUPAC Name

(2-{[(2S,3R)-3-hydroxy-2-[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienamido]nonadecyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R)-3-hydroxy-2-[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienamido]nonadecyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCC(O)\C=C\C=C\C\C=C\CCCCCCCC)[C@H](O)CCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C44H85N2O7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-36-43(48)42(40-53-54(50,51)52-39-38-46(3,4)5)45-44(49)37-33-35-41(47)34-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,27,29,31,34,41-43,47-48H,6-20,22,24-26,28,30,32-33,35-40H2,1-5H3,(H-,45,49,50,51)/b23-21+,29-27+,34-31+/t41?,42-,43+/m0/s1

InChI Key

OZEIXOVBZZHESF-FVMAXVDYSA-N

Chemical Taxonomy

Classification

Not classified

Functional Ontology

Physiological effect

Health effect

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (PMID: 30310470)

Vascular disorder

Atherosclerosis (PMID: 17963772)

Nervous system disorder

Central nervous system disorder

Pick's disease (PMID: 32310589)

Endocrine system disorder

Diabetes mellitus type 2 (PMID: 30310470)
Diabetes mellitus type 1 (PMID: 30310470)

Metabolic disorder

Metabolic syndrome (PMID: 21844222)

Disposition

Biological location

Cell

All cells and tissues (HMDB: HMDB0290657)

Cellular substructure

Organelle

Endoplasmic reticulum (PMID: 9009829)

Cell membrane (PMID: 9009829)
Golgi apparatus membrane (PMID: 11062253)

Source

Endogenous

Endogenous (HMDB: HMDB0290657)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (PMID: 8086039)

Role

Biological role

Nutrient (PMID: 23684760)

Industrial application

Pharmaceutical industry

Biomarker

Pick's disease ()
Diabetes mellitus type 2 ()
Cardiovascular disease ()
Insulin resistance ()
Atherosclerosis ()

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.7e-05 g/L	ALOGPS
logP	5.22	ALOGPS
logP	7.09	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-0.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.15 Å²	ChemAxon
Rotatable Bond Count	39	ChemAxon
Refractivity	240.85 m³·mol⁻¹	ChemAxon
Polarizability	97.7 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0290657

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for SM(d19:0/20:3(6,8,11)-OH(5)) (CFc000270173)

MOL for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

3D MOL for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

3D SDF for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

3D-SDF for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

PDB for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

3D PDB for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

SMILES for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

INCHI for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

Structure for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))

3D Structure for CFc000270173 (SM(d19:0/20:3(6,8,11)-OH(5)))