Structure Database (LMSD)

Common Name
Cer(d18:1/19:0)
Systematic Name
N-(nonadecanoyl)-sphing-4-enine
Synonyms
  • Cer[NS]
LM ID
LMSP02010032
Formula
C37H73NO3
Exact Mass
Calculate m/z
579.559044
Sum Composition
Cer 37:1;O2
Abbrev Chains
Cer 18:1;O2/19:0
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
Predict MS/MS spectrum ([M-H]-)

Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Ceramides [SP02]
N-acylsphingosines (ceramides) [SP0201]

Biological Context

C19 Ceramide is a naturally occurring ceramide that has been found in J. juncea extracts as well as rat brain and mouse heart.1,2,3 It is elevated in adult and decreased in juvenile whole rat brain extracts by 114 and 37%, respectively, following chronic ethanol exposure.2 C19 Ceramide is also increased in mouse hearts following administration of angiotensin II .3 [Matreya, LLC. Catalog No. 2039]

This information has been provided by Cayman Chemical

References

1. Roux, A., Muller, L., Jackson, S.N., et al. Chronic ethanol consumption profoundly alters regional brain ceramide and sphingomyelin content in rodents. ACS Chem Neurosci. 6(2), 247-259 (2015).
2. Glenn, D.J., Cardema, M.C., Ni, W., et al. Cardiac steatosis potentiates angiotensin II effects in the heart. Am. J. Physiol. Heart Circ. Physiol. 308(4), H339-350 (2015).
3. Krishna, N., Muralidhar, P., Kumar, M.M., et al. A new sphingolipid from the gorgonian Junceella juncea of the Indian ocean. Nat. Prod. Res. 18(6), 551-555 (2004).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
SNMLDULQFHAZRC-RQDJVNCUSA-N
InChi (Click to copy)
InChI=1S/C37H73NO3/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-33-37(41)38-35(34-39)36(40)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h30,32,35-36,39-40H,3-29,31,33-34H2,1-2H3,(H,38,41)/b32-30+/t35-,36+/m0/s1
SMILES (Click to copy)
[C@](CO)([H])(NC(CCCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

Other Databases

CHEBI ID
142377
PubChem CID
52931126
SwissLipids ID
SLM:000395712
Cayman ID
24395

Calculated Physicochemical Properties

Heavy Atoms 41
Rings 0
Aromatic Rings 0
Rotatable Bonds 33
Van der Waals Molecular Volume 680.75
Topological Polar Surface Area 69.56
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 11.59
Molar Refractivity 180.92

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