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Structure Database (LMSD)

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Common Name

Cer(t18:0)/24:0(2OH[R]))

Systematic Name

N-(2R-hydroxytetracosanoyl)-4R-hydroxyl-octadecasphinganine

Synonyms

N-(2R-hydroxytetracosanoyl)-4R-hydroxysphinganine
N-(2R-hydroxytetracosanoyl)-phytoceramide

LM ID

LMSP02030026

Formula

C₄₂H₈₅NO₅

Exact Mass

Calculate m/z

683.642774

Sum Composition

Cer 42:0;O4

Abbrev Chains

Cer 18:0;O3/24:0;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

C24 (2’(R)-hydroxy) Phytoceramide is a naturally occurring sphingolipid that has been found in adlay seed hull.¹ It inhibits LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages (IC50 = 19 μg/ml), as well as increases in COX-2 and inducible nitric oxide synthase (iNOS) levels. It increases production of chemokine (C-X-C motif) ligand 8 (CXCL8), CXCL1, chemokine (C-C motif) ligand 2 (CCL2), and CCL20 in human umbilical vein endothelial cells (HUVECs) in a concentration-dependent manner.² C24 (2’(R)-hydroxy) Phytoceramide is a hydroxylated form of C24 phytoceramide . [Matreya, LLC. Catalog No. 2094]

This information has been provided by Cayman Chemical

References

1. Huang, D.-W., Chung, C.-P., Kuo, Y.-H., et al. Identification of compounds in adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) seed hull extracts that inhibit lipopolysaccharide-induced inflammation in RAW 264.7 macrophages. J. Agric. Food Chem. 57(22), 10651-10657 (2009).

2. Sekiya, M., Ueda, K., Okazaki, K., et al. A phytoceramide analog stimulates the production of chemokines through CREB activation in human endothelial cells. Int. Immunopharmacol. 11(10), 1497-1503 (2011).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Russula cyanoxantha (#5403)

Agaricomycetes (#155619)

A new ceramide from the basidiomycete Russula cyanoxantha.,
Lipids, 2001

Pubmed ID: 11269698

String Representations

InChiKey (Click to copy)

ZFUXWVVVWGWGPQ-QLLOZFISSA-N

InChi (Click to copy)

InChI=1S/C42H85NO5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-40(46)42(48)43-38(37-44)41(47)39(45)35-33-31-29-27-25-16-14-12-10-8-6-4-2/h38-41,44-47H,3-37H2,1-2H3,(H,43,48)/t38-,39+,40+,41-/m0/s1

SMILES (Click to copy)

[C@@]([C@]([H])(O)[C@H](O)CCCCCCCCCCCCCC)(CO)([H])NC([C@H](O)CCCCCCCCCCCCCCCCCCCCCC)=O