LIPID MAPS

Structure Database (LMSD)

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Common Name

Cer(d18:1/12:0)

Systematic Name

N-(dodecanoyl)-sphing-4-enine

Synonyms

N-(dodecanoyl)-ceramide
N-(dodecanoyl)-ceramide
Cer[NS]

LM ID

LMSP02010002

Formula

C₃₀H₅₉NO₃

Exact Mass

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481.449494

Sum Composition

Cer 30:1;O2

Abbrev Chains

Cer 18:1;O2/12:0

Status

Curated

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Classification

Biological Context

C12 ceramide is a naturally occurring ceramide that is formed when C12 sphingomyelin is hydrolyzed by acid sphingomyelinase (ASM).¹ It is a substrate for acid ceramidase, an enzyme that has 2- to 12-fold higher activity in fibroblasts from patients with Farber disease, a lipid storage disorder.² C12 ceramide is found in the Wharton's jelly, a protective coating that surrounds umbilical cord vessels, of babies born to women with pre-eclampsia.³ BODIPY C12 ceramide has been used to assess levels of ASM activity in plasma of patients with type A or B Niemann-Pick disease.¹

This information has been provided by Cayman Chemical

References

1. Romanowicz, L., and Bańkowski, E. Altered sphingolipid composition in Wharton’s jelly of pre-eclamptic newborns. Pathobiology 77(2), 78-87 (2010).

2. Momoi, T., Ben-Yoseph, Y., and Nadler, H.L. Substrate-specificities of acid and alkaline ceramidases in fibroblasts from patients with Farber disease and controls. Biochem. J. 205(2), 419-425 (1982).

3. He, X., Chen, F., Dagan, A., et al. A fluorescence-based, high-performance liquid chromatographic assay to determine acid sphingomyelinase activity and diagnose types A and B Niemann-Pick disease. Anal. Biochem. 314(1), 116-120 (2003).

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String Representations

InChiKey (Click to copy)

HXFPPRPLRSPNIB-VARSQMIESA-N

InChi (Click to copy)

InChI=1S/C30H59NO3/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-29(33)28(27-32)31-30(34)26-24-22-20-17-12-10-8-6-4-2/h23,25,28-29,32-33H,3-22,24,26-27H2,1-2H3,(H,31,34)/b25-23+/t28-,29+/m0/s1

SMILES (Click to copy)

OC[C@]([H])(NC(=O)CCCCCCCCCCC)[C@]([H])(O)/C=C/CCCCCCCCCCCCC