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Structure Database (LMSD)

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Common Name

Cer(t18:0/16:0)

Systematic Name

N-(hexadecanoyl)-4R-hydroxysphinganine

Synonyms

N-(hexadecanoyl)-phytoceramide
N-(palmitoyl)-phytoceramide
Cer[NP]

LM ID

LMSP02030001

Formula

C₃₄H₆₉NO₄

Exact Mass

Calculate m/z

555.522659

Sum Composition

Cer 34:0;O3

Abbrev Chains

Cer 18:0;O3/16:0

Status

Curated

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Classification

Biological Context

C16 Phytoceramide (t18:0/16:0) is a phytoceramide, which is a family of sphingolipids found in the intestine, kidney, and extracellular spaces of the stratum corneum of the mammalian epidermis.^1,2,3 C16 Phytoceramide (t18:0/16:0) is composed of a phytosphingosine backbone amine-linked to a C16 fatty acid chain. The levels of C16 phytoceramide (t18:0/16:0) increase following heat stress in S. cerevisiae.⁴ It has been used with other ceramides to create stratum corneum substitutes to study percutaneous penetration and psoriasis in vitro.^5,6 [Matreya, LLC. Catalog No. 2035]

This information has been provided by Cayman Chemical

References

1. Montefusco, D.J., Chen, L., Matmati, N., et al. Distinct signaling roles of ceramide species in yeast revealed through systematic perturbation and systems biology analyses. Sci. Signal 6(299), rs14 (2013).

2. de Jager, M., Groenink, W., van der Spek, J., et al. Preparation and characterization of a stratum corneum substitute for in vitro percutaneous penetration studies. Biochim. Biophys. Acta 1758(5), 636-644 (2006).

3. Basse, L.H., Groen, D., and Bouwstra, J.A. Permeability and lipid organization of a novel psoriasis stratum corneum substitute. Int. J. Pharm. 457(1), 275-282 (2013).

4. Crossman, M.W., and Hirschberg, C.B. Biosynthesis of phytosphingosine by the rat. The Journal of Biological Chemisty 252(16), 5815-5819 (1977).

5. Mizutani, Y., Kihara, A., and Igarashi, Y. Identification of the human sphingolipid C4-hydroxylase, hDES2, and its up-regulation during keratinocyte differentiation. FEBS Lett. 563(1-3), 93-97 (2004).

6. Omae, F., Miyazaki, M., Enomoto, A., et al. DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine. Biochem J. 379(Pt. 3), 687-695 (2004).

String Representations

InChiKey (Click to copy)

IVBULNXGVIHEKN-MVIDNBQJSA-N

InChi (Click to copy)

InChI=1S/C34H69NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(38)35-31(30-36)34(39)32(37)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h31-32,34,36-37,39H,3-30H2,1-2H3,(H,35,38)/t31-,32+,34-/m0/s1

SMILES (Click to copy)

OC[C@]([H])(NC(=O)CCCCCCCCCCCCCCC)[C@]([H])(O)[C@H](O)CCCCCCCCCCCCCC