MiMeDB: Showing metabocard for Cer(d18:1/16:0) (MMDBc0000607)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:59 UTC

Update Date

2025-01-15 20:38:48 UTC

Metabolite ID

MMDBc0000607

Metabolite Identification

Common Name

Cer(d18:1/16:0)

Description

Ceramides, also known as N-acylsphingosines, consist of a sphingoid base linked to a fatty acid chain via the amine group. Ceramides are one of the hydrolysis byproducts of sphingomyelin via the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase, E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis and many other tissues (PMID: 25935 ). They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID: 14998372 ). Ceramides are key to the biosynthesis of glycosphingolipids and gangliosides. Cer(d18:1/16:0), in particular, consists of a monounsaturated 18-carbon dihydroxylated sphingoid base linked to one chain of palmitic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3R,4E)-2-Acylamino-1,3-octadec-4-enediol	ChEBI
(2S,3R,4E)-2-Acylaminooctadec-4-ene-1,3-diol	ChEBI
C16 Cer	ChEBI
C16 Ceramide	ChEBI
C16-0(Palmitoyl)ceramide	ChEBI
Ceramide (D18:1/16:0)	ChEBI
N-(Hexadecanoyl)-sphing-4-enine	ChEBI
N-(Hexadecanoyl)ceramide	ChEBI
N-(Hexadecanoyl)sphing-4-enine	ChEBI
N-(Palmitoyl)ceramide	ChEBI
N-Hexadecanoyl-D-erythro-sphingosine	ChEBI
N-Hexadecanoylsphing-4-enine	ChEBI
N-Palmitoyl-sphingosine	ChEBI
N-Palmitoylsphing-4-enine	ChEBI
N-Palmitoylsphingosine	ChEBI
Cer	HMDB
Ceramide	HMDB
N-Acylsphingosine	HMDB
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamide	HMDB
C16-Ceramide	HMDB
NFA(C16)cer	HMDB
Palmitoylceramide	HMDB
C(16)-Ceramide	HMDB
N-Palmitoylsphingosine, (r,s-(e))-(+-)	HMDB
C16-Palmitoylceramide	HMDB
N-Palmitoylsphingosine, R-(r,s-(e))	HMDB
PCer CPD	HMDB
Ceramide-C16	HMDB
(2S,3R,4E)-2-N-Palmitoyloctadecasphinga-4-ene	HMDB
C16:0-Ceramide	HMDB
Ceramide (D18:1,C16:0)	HMDB
Ceramide 16	HMDB
Ceramide(D18:1/16:0)	HMDB
D-Erythro-C16-ceramide	HMDB
D-Erythro-N-hexadecanoylsphingenine	HMDB
D-Erythro-N-palmitoylsphingosine	HMDB
D-Erythro-delta4-ceramide	HMDB
D-Erythro-δ4-ceramide	HMDB
N-Hexadecanoyl-D-erythro-ceramide	HMDB
N-Hexadecanoylsphingosine	HMDB
N-Palmitoyl 4-sphingenine	HMDB
N-Palmitoyl ceramide	HMDB
N-Palmitoyl-D-erythro-sphingosine	HMDB
N-Palmitoyl-D-sphingosine	HMDB
N-(Hexadecanoyl)-sphingosine	MetBuilder
N-(Hexadecanoyl)-D-erythro-sphingosine	MetBuilder
N-(Hexadecanoyl)-4-sphingenine	MetBuilder
N-(Hexadecanoyl)-D-sphingosine	MetBuilder
N-(Hexadecanoyl)-sphingenine	MetBuilder
N-(Hexadecanoyl)-erythro-4-sphingenine	MetBuilder
Cer(D18:1/16:0)	ChEBI

Molecular Formula

C₃₄H₆₇NO₃

Average Mass

537.9007

Monoisotopic Mass

537.512095

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+/t32-,33+/m0/s1

InChI Key

YDNKGFDKKRUKPY-TURZORIXSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191837	Isovaleryl-CoA dehydrogenase, mitochondrial	Unknown	P26440	Homo sapiens
MMDBp0191901	Lipid phosphate phosphohydrolase 2	Unknown	O43688	Homo sapiens
MMDBp0191907	Lipid phosphate phosphohydrolase 1	Unknown	O14494	Homo sapiens
MMDBp0191912	Lipid phosphate phosphohydrolase 3	Unknown	O14495	Homo sapiens
MMDBp0191985	Galactocerebrosidase	Enzyme	P54803	Homo sapiens
MMDBp0192033	Lactase-phlorizin hydrolase	Enzyme	P09848	Homo sapiens
MMDBp0192100	Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1	Unknown	Q8N5D6	Homo sapiens
MMDBp0192162	Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial	Enzyme	Q9HCC0	Homo sapiens
MMDBp0192164	Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial	Enzyme	Q96RQ3	Homo sapiens
MMDBp0192203	N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase	Enzyme	Q9Y2B2	Homo sapiens
MMDBp0192238	Probable leucine--tRNA ligase, mitochondrial	Enzyme	Q15031	Homo sapiens
MMDBp0192289	Leucine--tRNA ligase, cytoplasmic	Enzyme	Q9P2J5	Homo sapiens
MMDBp0192391	Phosphatidylcholine:ceramide cholinephosphotransferase 2	Enzyme	Q8NHU3	Homo sapiens
MMDBp0192395	Phosphatidylcholine:ceramide cholinephosphotransferase 1	Enzyme	Q86VZ5	Homo sapiens
MMDBp0192396	Sphingomyelin phosphodiesterase	Enzyme	P17405	Homo sapiens
MMDBp0192465	Ceramide glucosyltransferase	Enzyme	Q16739	Homo sapiens
MMDBp0192558	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q	Enzyme	Q9BRB3	Homo sapiens
MMDBp0192559	Phosphatidylinositol N-acetylglucosaminyltransferase subunit A	Enzyme	P37287	Homo sapiens
MMDBp0192560	Phosphatidylinositol N-acetylglucosaminyltransferase subunit H	Enzyme	Q14442	Homo sapiens
MMDBp0192561	Phosphatidylinositol N-acetylglucosaminyltransferase subunit P	Enzyme	P57054	Homo sapiens
MMDBp0192562	Phosphatidylinositol N-acetylglucosaminyltransferase subunit C	Enzyme	Q92535	Homo sapiens
MMDBp0192594	Methylglutaconyl-CoA hydratase, mitochondrial	Enzyme	Q13825	Homo sapiens
MMDBp0192661	Sphingosine-1-phosphate lyase 1	Enzyme	O95470	Homo sapiens
MMDBp0192688	Sphingosine kinase 1	Unknown	Q9NYA1	Homo sapiens
MMDBp0192690	Acid ceramidase	Enzyme	Q13510	Homo sapiens
MMDBp0192695	Ectonucleotide pyrophosphatase/phosphodiesterase family member 7	Unknown	Q6UWV6	Homo sapiens
MMDBp0192696	Sphingomyelin phosphodiesterase 2	Unknown	O60906	Homo sapiens
MMDBp0192707	2-hydroxyacylsphingosine 1-beta-galactosyltransferase	Enzyme	Q16880	Homo sapiens
MMDBp0192889	Collagen type IV alpha-3-binding protein	Enzyme	Q9Y5P4	Homo sapiens
MMDBp0192976	Ceramide kinase	Unknown	Q8TCT0	Homo sapiens
MMDBp0193223	Ganglioside GM2 activator	Enzyme	P17900	Homo sapiens
MMDBp0193267	Glucosylceramidase	Enzyme	P04062	Homo sapiens
MMDBp0193531	T-cell surface glycoprotein CD1e, membrane-associated	Enzyme	P15812	Homo sapiens
MMDBp0193636	Epididymal secretory protein E1	Enzyme	P61916	Homo sapiens
MMDBp0193670	Ceramide synthase 1	Enzyme	P27544	Homo sapiens
MMDBp0193673	Antigen-presenting glycoprotein CD1d	Enzyme	P15813	Homo sapiens
MMDBp0193742	GPI mannosyltransferase 1	Enzyme	Q9H3S5	Homo sapiens
MMDBp0193755	Phosphatidylinositol-glycan biosynthesis class W protein	Enzyme	Q7Z7B1	Homo sapiens
MMDBp0193805	Phosphatidylinositol-glycan biosynthesis class X protein	Enzyme	Q8TBF5	Homo sapiens
MMDBp0193806	GPI mannosyltransferase 4	Enzyme	Q86VD9	Homo sapiens
MMDBp0194033	Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase	Enzyme	Q9BYG0	Homo sapiens
MMDBp0194037	Sphingomyelin phosphodiesterase 3	Unknown	Q9NY59	Homo sapiens
MMDBp0194044	Beta-1,3-galactosyltransferase 5	Enzyme	Q9Y2C3	Homo sapiens
MMDBp0194119	GPI mannosyltransferase 3	Enzyme	Q92521	Homo sapiens
MMDBp0194120	Phosphatidylinositol-glycan biosynthesis class F protein	Enzyme	Q07326	Homo sapiens
MMDBp0194121	GPI ethanolamine phosphate transferase 2	Enzyme	Q5H8A4	Homo sapiens
MMDBp0194122	GPI ethanolamine phosphate transferase 1	Enzyme	O95427	Homo sapiens
MMDBp0194123	GPI ethanolamine phosphate transferase 3	Enzyme	Q8TEQ8	Homo sapiens
MMDBp0194124	GPI transamidase component PIG-S	Enzyme	Q96S52	Homo sapiens
MMDBp0194125	GPI transamidase component PIG-T	Enzyme	Q969N2	Homo sapiens
MMDBp0194126	Phosphatidylinositol glycan anchor biosynthesis class U protein	Enzyme	Q9H490	Homo sapiens
MMDBp0194127	GPI mannosyltransferase 2	Enzyme	Q9NUD9	Homo sapiens
MMDBp0194128	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y	Enzyme	Q3MUY2	Homo sapiens
MMDBp0194133	Pleckstrin homology domain-containing family A member 8	Unknown	Q96JA3	Homo sapiens
MMDBp0195538	Sphingomyelin phosphodiesterase 4	Unknown	Q9NXE4	Homo sapiens
MMDBp0195879	Putative neutral ceramidase C	Enzyme	P0C7U2	Homo sapiens
MMDBp0195880	Alkaline ceramidase 2	Enzyme	Q5QJU3	Homo sapiens
MMDBp0195881	Neutral ceramidase	Enzyme	Q9NR71	Homo sapiens
MMDBp0195885	Non-lysosomal glucosylceramidase	Enzyme	Q9HCG7	Homo sapiens
MMDBp0196227	Alkaline ceramidase 1	Enzyme	Q8TDN7	Homo sapiens
MMDBp0196313	Killer cell lectin-like receptor subfamily B member 1	Unknown	Q12918	Homo sapiens
MMDBp0196460	Protein FAN	Enzyme	Q92636	Homo sapiens
MMDBp0196494	Ceramide synthase 5	Unknown	Q8N5B7	Homo sapiens
MMDBp0196495	ATP-binding cassette sub-family A member 7	Unknown	Q8IZY2	Homo sapiens
MMDBp0196528	GPI-anchor transamidase	Enzyme	Q92643	Homo sapiens
MMDBp0196556	Glycosylphosphatidylinositol anchor attachment 1 protein	Unknown	O43292	Homo sapiens
MMDBp0196557	Protein PLEKHA9	Unknown	O95397	Homo sapiens
MMDBp0196558	Glycolipid transfer protein domain-containing protein 2	Unknown	A6NH11	Homo sapiens
MMDBp0196559	Putative uncharacterized protein PLEKHA8	Unknown	B5MDU3	Homo sapiens
MMDBp0196560	T-cell surface glycoprotein CD1a	Unknown	P06126	Homo sapiens
MMDBp0196561	Glycolipid transfer protein domain-containing protein 1	Unknown	Q5TA50	Homo sapiens
MMDBp0196562	T-cell surface glycoprotein CD1c	Unknown	P29017	Homo sapiens
MMDBp0196563	Lipopolysaccharide-binding protein	Unknown	P18428	Homo sapiens
MMDBp0196564	Putative uncharacterized protein DKFZp434L0435	Unknown	Q9UFH6	Homo sapiens
MMDBp0196565	T-cell surface glycoprotein CD1b	Unknown	P29016	Homo sapiens
MMDBp0196566	Glycolipid transfer protein	Unknown	Q9NZD2	Homo sapiens

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.008	0.001	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.012	0.001	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.022	0.001	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.036	0.002	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.040	0.002	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.061	0.0007	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.128	0.012	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.145	0.007	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.271	0.013	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.281	0.033	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.331	0.029	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	1.00	0.029	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	1.22	0.046	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	3.00	0.107	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Brain	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Thyroid gland	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

References

General References

Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. doi: 10.1111/1523-1747.ep12543516. [PubMed:25935 ]
Dunn HG, Dolman CL, Farrell DF, Tischler B, Hasinoff C, Woolf LI: Krabbe's leukodystrophy without globoid cells. Neurology. 1976 Nov;26(11):1035-41. doi: 10.1212/wnl.26.11.1035. [PubMed:988509 ]
Ogawa-Goto K, Funamoto N, Abe T, Nagashima K: Different ceramide compositions of gangliosides between human motor and sensory nerves. J Neurochem. 1990 Nov;55(5):1486-93. doi: 10.1111/j.1471-4159.1990.tb04930.x. [PubMed:2213006 ]
Ogawa-Goto K, Ohta Y, Kubota K, Funamoto N, Abe T, Taki T, Nagashima K: Glycosphingolipids of human peripheral nervous system myelins isolated from cauda equina. J Neurochem. 1993 Oct;61(4):1398-403. doi: 10.1111/j.1471-4159.1993.tb13633.x. [PubMed:7690848 ]
Ghadially R, Brown BE, Sequeira-Martin SM, Feingold KR, Elias PM: The aged epidermal permeability barrier. Structural, functional, and lipid biochemical abnormalities in humans and a senescent murine model. J Clin Invest. 1995 May;95(5):2281-90. doi: 10.1172/JCI117919. [PubMed:7738193 ]
Marchesini S, Demasi L, Cestone P, Preti A, Agmon V, Dagan A, Navon R, Gatt S: Sulforhodamine GM1-ganglioside: synthesis and physicochemical properties. Chem Phys Lipids. 1994 Aug 8;72(2):143-52. doi: 10.1016/0009-3084(94)90098-1. [PubMed:7954976 ]
Tojo K, Oota M, Honda H, Shibasaki T, Sakai O: Possible thyroidal involvement in a case of Fabry disease. Intern Med. 1994 Mar;33(3):172-6. doi: 10.2169/internalmedicine.33.172. [PubMed:8061397 ]
Holleran WM, Ginns EI, Menon GK, Grundmann JU, Fartasch M, McKinney CE, Elias PM, Sidransky E: Consequences of beta-glucocerebrosidase deficiency in epidermis. Ultrastructure and permeability barrier alterations in Gaucher disease. J Clin Invest. 1994 Apr;93(4):1756-64. doi: 10.1172/JCI117160. [PubMed:8163674 ]
Schafer A, Harzer K, Kattner E, Schafer HJ, Stoltenburg G, Lietz H: [Disseminated lipogranulomatosis (Farber disease) with hydrops fetalis]. Pathologe. 1996 Mar;17(2):145-9. doi: 10.1007/s002920050148. [PubMed:8650144 ]
Sando GN, Howard EJ, Madison KC: Induction of ceramide glucosyltransferase activity in cultured human keratinocytes. Correlation with culture differentiation. J Biol Chem. 1996 Sep 6;271(36):22044-51. doi: 10.1074/jbc.271.36.22044. [PubMed:8703011 ]
Futerman AH: The roles of ceramide in the regulation of neuronal growth and development. Biochemistry (Mosc). 1998 Jan;63(1):74-83. [PubMed:9526098 ]
Watanabe R, Wu K, Paul P, Marks DL, Kobayashi T, Pittelkow MR, Pagano RE: Up-regulation of glucosylceramide synthase expression and activity during human keratinocyte differentiation. J Biol Chem. 1998 Apr 17;273(16):9651-5. doi: 10.1074/jbc.273.16.9651. [PubMed:9545298 ]
Ohnishi Y, Okino N, Ito M, Imayama S: Ceramidase activity in bacterial skin flora as a possible cause of ceramide deficiency in atopic dermatitis. Clin Diagn Lab Immunol. 1999 Jan;6(1):101-4. doi: 10.1128/CDLI.6.1.101-104.1999. [PubMed:9874672 ]
Gill JS, Windebank AJ: Suramin induced ceramide accumulation leads to apoptotic cell death in dorsal root ganglion neurons. Cell Death Differ. 1998 Oct;5(10):876-83. doi: 10.1038/sj.cdd.4400410. [PubMed:10203686 ]
Herr I, Martin-Villalba A, Kurz E, Roncaioli P, Schenkel J, Cifone MG, Debatin KM: FK506 prevents stroke-induced generation of ceramide and apoptosis signaling. Brain Res. 1999 May 1;826(2):210-9. doi: 10.1016/s0006-8993(99)01288-3. [PubMed:10224298 ]
Di Marzio L, Cinque B, De Simone C, Cifone MG: Effect of the lactic acid bacterium Streptococcus thermophilus on ceramide levels in human keratinocytes in vitro and stratum corneum in vivo. J Invest Dermatol. 1999 Jul;113(1):98-106. doi: 10.1046/j.1523-1747.1999.00633.x. [PubMed:10417626 ]
Farina F, Cappello F, Todaro M, Bucchieri F, Peri G, Zummo G, Stassi G: Involvement of caspase-3 and GD3 ganglioside in ceramide-induced apoptosis in Farber disease. J Histochem Cytochem. 2000 Jan;48(1):57-62. doi: 10.1177/002215540004800106. [PubMed:10653586 ]
Bektas M, Orfanos CE, Geilen CC: Different vitamin D analogues induce sphingomyelin hydrolysis and apoptosis in the human keratinocyte cell line HaCaT. Cell Mol Biol (Noisy-le-grand). 2000 Feb;46(1):111-9. [PubMed:10726977 ]
Garcia-Ruiz C, Mari M, Morales A, Colell A, Ardite E, Fernandez-Checa JC: Human placenta sphingomyelinase, an exogenous acidic pH-optimum sphingomyelinase, induces oxidative stress, glutathione depletion, and apoptosis in rat hepatocytes. Hepatology. 2000 Jul;32(1):56-65. doi: 10.1053/jhep.2000.8267. [PubMed:10869289 ]
Tanno O, Ota Y, Kitamura N, Katsube T, Inoue S: Nicotinamide increases biosynthesis of ceramides as well as other stratum corneum lipids to improve the epidermal permeability barrier. Br J Dermatol. 2000 Sep;143(3):524-31. doi: 10.1111/j.1365-2133.2000.03705.x. [PubMed:10971324 ]
van Lijnschoten G, Groener JE, Maas SM, Ben-Yoseph Y, Dingemans KP, Offerhaus GJ: Intrauterine fetal death due to Farber disease: case report. Pediatr Dev Pathol. 2000 Nov-Dec;3(6):597-602. doi: 10.1007/s100240010107. [PubMed:11000338 ]
Grether-Beck S, Bonizzi G, Schmitt-Brenden H, Felsner I, Timmer A, Sies H, Johnson JP, Piette J, Krutmann J: Non-enzymatic triggering of the ceramide signalling cascade by solar UVA radiation. EMBO J. 2000 Nov 1;19(21):5793-800. doi: 10.1093/emboj/19.21.5793. [PubMed:11060030 ]
Maurer BJ, Melton L, Billups C, Cabot MC, Reynolds CP: Synergistic cytotoxicity in solid tumor cell lines between N-(4-hydroxyphenyl)retinamide and modulators of ceramide metabolism. J Natl Cancer Inst. 2000 Dec 6;92(23):1897-909. doi: 10.1093/jnci/92.23.1897. [PubMed:11106681 ]
Sugiki H, Hozumi Y, Maeshima H, Katagata Y, Mitsuhashi Y, Kondo S: C2-ceramide induces apoptosis in a human squamous cell carcinoma cell line. Br J Dermatol. 2000 Dec;143(6):1154-63. doi: 10.1046/j.1365-2133.2000.03882.x. [PubMed:11122015 ]
Poliak S, Gollan L, Salomon D, Berglund EO, Ohara R, Ranscht B, Peles E: Localization of Caspr2 in myelinated nerves depends on axon-glia interactions and the generation of barriers along the axon. J Neurosci. 2001 Oct 1;21(19):7568-75. [PubMed:11567047 ]
Yarosh DB, Both D, Brown D: Liposomal ursolic acid (merotaine) increases ceramides and collagen in human skin. Horm Res. 2000;54(5-6):318-21. doi: 10.1159/000053280. [PubMed:11595826 ]
Vielhaber G, Pfeiffer S, Brade L, Lindner B, Goldmann T, Vollmer E, Hintze U, Wittern KP, Wepf R: Localization of ceramide and glucosylceramide in human epidermis by immunogold electron microscopy. J Invest Dermatol. 2001 Nov;117(5):1126-36. doi: 10.1046/j.0022-202x.2001.01527.x. [PubMed:11710923 ]
Uchida Y, Behne M, Quiec D, Elias PM, Holleran WM: Vitamin C stimulates sphingolipid production and markers of barrier formation in submerged human keratinocyte cultures. J Invest Dermatol. 2001 Nov;117(5):1307-13. doi: 10.1046/j.0022-202x.2001.01555.x. [PubMed:11710949 ]
Kirby RJ, Zheng S, Tso P, Howles PN, Hui DY: Bile salt-stimulated carboxyl ester lipase influences lipoprotein assembly and secretion in intestine: a process mediated via ceramide hydrolysis. J Biol Chem. 2002 Feb 8;277(6):4104-9. doi: 10.1074/jbc.M107549200. Epub 2001 Dec 3. [PubMed:11733511 ]
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Bouwstra JA, Honeywell-Nguyen PL, Gooris GS, Ponec M: Structure of the skin barrier and its modulation by vesicular formulations. Prog Lipid Res. 2003 Jan;42(1):1-36. doi: 10.1016/s0163-7827(02)00028-0. [PubMed:12467638 ]
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Showing metabocard for Cer(d18:1/16:0) (MMDBc0000607)

MOL for #<Metabolite:0x00007fb7dae7c590>

3D MOL for #<Metabolite:0x00007fb7dae7c590>

3D SDF for #<Metabolite:0x00007fb7dae7c590>

3D-SDF for #<Metabolite:0x00007fb7dae7c590>

PDB for #<Metabolite:0x00007fb7dae7c590>

3D PDB for #<Metabolite:0x00007fb7dae7c590>

SMILES for #<Metabolite:0x00007fb7dae7c590>

INCHI for #<Metabolite:0x00007fb7dae7c590>

Structure for #<Metabolite:0x00007fb7dae7c590>

3D Structure for #<Metabolite:0x00007fb7dae7c590>