Human Metabolome Database Version 3.5

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Showing metabocard for Cer(d18:0/25:0) (HMDB11770)

enzymes (66)

Blood
Urine

Record Information

Version

3.5

Creation Date

2009-03-24 10:16:38 -0600

Update Date

2013-02-08 17:27:20 -0700

HMDB ID

HMDB11770

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cer(d18:0/25:0)

Description

Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935 Link_out

) and many other tissues. 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 Link_out

). Is key in the biosynthesis of glycosphingolipids and gangliosides.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Chemical Formula

C₄₃H₈₇NO₃

Average Molecular Weight

666.1558

Monoisotopic Molecular Weight

665.668595655

IUPAC Name

N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]pentacosanamide

Traditional IUPAC Name

N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]pentacosanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C43H87NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-43(47)44-41(40-45)42(46)38-36-34-32-30-28-26-16-14-12-10-8-6-4-2/h41-42,45-46H,3-40H2,1-2H3,(H,44,47)/t41-,42+/m0/s1

InChI Key

HCDLRJUFVJOBJP-ACEXITHZSA-N

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Lipids

Class

Sphingolipids

Sub Class

Ceramides

Other Descriptors

Aliphatic Acyclic Compounds

Substituents

Carboxamide Group
N Acyl Amine
Primary Alcohol
Secondary Alcohol
Secondary Carboxylic Acid Amide

Direct Parent

Ceramides

Ontology

Status

Expected and Not Quantified

Origin

Endogenous

Food

Biofunction

Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability

Application

Nutrients
Stabilizers
Surfactants and Emulsifiers

Cellular locations

Extracellular
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.040E-05 g/L	ALOGPS
LogP	10.31	ALOGPS
LogP	15.07	ChemAxon
LogS	-7.51	ALOGPS
pKa (strongest acidic)	13.83	ChemAxon
pKa (strongest basic)	0.034	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 A²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	206.22	ChemAxon
Polarizability	93	ChemAxon
Formal Charge	0	ChemAxon
Physiological Charge	0	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB028440

KNApSAcK ID

Not Available

Chemspider ID

24765765

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

NuGOwiki Link

HMDB11770

Metagene Link

HMDB11770

METLIN ID

Not Available

PubChem Compound

53481050

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Name:	Galactocerebrosidase
Reactions:	D-galactosyl-N-acylsphingosine + H2O = D-galactose + N-acylsphingosine [RN:R03617]
Gene Name:	GALC
Uniprot ID:	P54803
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1
Reactions:
Gene Name:	GBGT1
Uniprot ID:	Q8N5D6
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase
Reactions:	6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O = 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate [RN:R03482 R05917]
Gene Name:	PIGL
Uniprot ID:	Q9Y2B2
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylcholine:ceramide cholinephosphotransferase 2
Reactions:	a ceramide + a phosphatidylcholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol [RN:R08969]
Gene Name:	SGMS2
Uniprot ID:	Q8NHU3
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylcholine:ceramide cholinephosphotransferase 1
Reactions:	a ceramide + a phosphatidylcholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol [RN:R08969]
Gene Name:	SGMS1
Uniprot ID:	Q86VZ5
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Sphingomyelin phosphodiesterase
Reactions:	sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541]
Gene Name:	SMPD1
Uniprot ID:	P17405
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Ceramide glucosyltransferase
Reactions:	UDP-glucose + an N-acylsphingosine = UDP + a D-glucosyl-N-acylsphingosine [RN:R01497 R06275]
Gene Name:	UGCG
Uniprot ID:	Q16739
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
Reactions:	UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916]
Gene Name:	PIGQ
Uniprot ID:	Q9BRB3
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
Reactions:	UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916]
Gene Name:	PIGA
Uniprot ID:	P37287
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol N-acetylglucosaminyltransferase subunit H
Reactions:	UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916]
Gene Name:	PIGH
Uniprot ID:	Q14442
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol N-acetylglucosaminyltransferase subunit P
Reactions:	UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916]
Gene Name:	PIGP
Uniprot ID:	P57054
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol N-acetylglucosaminyltransferase subunit C
Reactions:	UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916]
Gene Name:	PIGC
Uniprot ID:	Q92535
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Sphingosine-1-phosphate lyase 1
Reactions:	sphinganine 1-phosphate = phosphoethanolamine + palmitaldehyde [RN:R02464]
Gene Name:	SGPL1
Uniprot ID:	O95470
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Sphingosine kinase 1
Reactions:	ATP + sphinganine = ADP + sphinganine 1-phosphate [RN:R02976]
Gene Name:	SPHK1
Uniprot ID:	Q9NYA1
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Acid ceramidase
Reactions:	N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
Gene Name:	ASAH1
Uniprot ID:	Q13510
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Ectonucleotide pyrophosphatase/phosphodiesterase family member 7
Reactions:	sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541]
Gene Name:	ENPP7
Uniprot ID:	Q6UWV6
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Sphingomyelin phosphodiesterase 2
Reactions:	sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541]
Gene Name:	SMPD2
Uniprot ID:	O60906
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	2-hydroxyacylsphingosine 1-beta-galactosyltransferase
Reactions:	UDP-galactose + 2-(2-hydroxyacyl)sphingosine = UDP + 1-(beta-D-galactosyl)-2-(2-hydroxyacyl)sphingosine [RN:R04322]
Gene Name:	UGT8
Uniprot ID:	Q16880
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Collagen type IV alpha-3-binding protein
Reactions:
Gene Name:	COL4A3BP
Uniprot ID:	Q9Y5P4
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Ceramide kinase
Reactions:	ATP + ceramide = ADP + ceramide 1-phosphate [RN:R01495]
Gene Name:	CERK
Uniprot ID:	Q8TCT0
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Ganglioside GM2 activator
Reactions:
Gene Name:	GM2A
Uniprot ID:	P17900
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Glucosylceramidase
Reactions:	D-glucosyl-N-acylsphingosine + H2O = D-glucose + N-acylsphingosine [RN:R01498]
Gene Name:	GBA
Uniprot ID:	P04062
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	T-cell surface glycoprotein CD1e, membrane-associated
Reactions:
Gene Name:	CD1E
Uniprot ID:	P15812
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Epididymal secretory protein E1
Reactions:
Gene Name:	NPC2
Uniprot ID:	P61916
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	LAG1 longevity assurance homolog 1
Reactions:
Gene Name:	LASS1
Uniprot ID:	P27544
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Antigen-presenting glycoprotein CD1d
Reactions:
Gene Name:	CD1D
Uniprot ID:	P15813
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI mannosyltransferase 1
Reactions:
Gene Name:	PIGM
Uniprot ID:	Q9H3S5
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol-glycan biosynthesis class W protein
Reactions:
Gene Name:	PIGW
Uniprot ID:	Q7Z7B1
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol-glycan biosynthesis class X protein
Reactions:
Gene Name:	PIGX
Uniprot ID:	Q8TBF5
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI mannosyltransferase 4
Reactions:
Gene Name:	PIGZ
Uniprot ID:	Q86VD9
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	UDP-GlcNAc:betaGal beta-1,3-N-acetylglucosaminyltransferase 5
Reactions:
Gene Name:	B3GNT5
Uniprot ID:	Q9BYG0
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Sphingomyelin phosphodiesterase 3
Reactions:	sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541]
Gene Name:	SMPD3
Uniprot ID:	Q9NY59
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Beta-1,3-galactosyltransferase 5
Reactions:
Gene Name:	B3GALT5
Uniprot ID:	Q9Y2C3
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI mannosyltransferase 3
Reactions:
Gene Name:	PIGB
Uniprot ID:	Q92521
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol-glycan biosynthesis class F protein
Reactions:
Gene Name:	PIGF
Uniprot ID:	Q07326
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI ethanolamine phosphate transferase 2
Reactions:
Gene Name:	PIGG
Uniprot ID:	Q5H8A4
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI ethanolamine phosphate transferase 1
Reactions:
Gene Name:	PIGN
Uniprot ID:	O95427
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI ethanolamine phosphate transferase 3
Reactions:
Gene Name:	PIGO
Uniprot ID:	Q8TEQ8
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI transamidase component PIG-S
Reactions:
Gene Name:	PIGS
Uniprot ID:	Q96S52
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI transamidase component PIG-T
Reactions:
Gene Name:	PIGT
Uniprot ID:	Q969N2
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol glycan anchor biosynthesis class U protein
Reactions:
Gene Name:	PIGU
Uniprot ID:	Q9H490
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI mannosyltransferase 2
Reactions:
Gene Name:	PIGV
Uniprot ID:	Q9NUD9
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y
Reactions:
Gene Name:	PIGY
Uniprot ID:	Q3MUY2
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Pleckstrin homology domain-containing family A member 8
Reactions:
Gene Name:	PLEKHA8
Uniprot ID:	Q96JA3
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Sphingomyelin phosphodiesterase 4
Reactions:	sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541]
Gene Name:	SMPD4
Uniprot ID:	Q9NXE4
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Putative neutral ceramidase C
Reactions:	N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
Gene Name:	ASAH2C
Uniprot ID:	P0C7U2
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Alkaline ceramidase 2
Reactions:	N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
Gene Name:	ACER2
Uniprot ID:	Q5QJU3
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Neutral ceramidase
Reactions:	N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
Gene Name:	ASAH2
Uniprot ID:	Q9NR71
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Non-lysosomal glucosylceramidase
Reactions:	D-glucosyl-N-acylsphingosine + H2O = D-glucose + N-acylsphingosine [RN:R01498]
Gene Name:	GBA2
Uniprot ID:	Q9HCG7
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Alkaline ceramidase 1
Reactions:	N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
Gene Name:	ACER1
Uniprot ID:	Q8TDN7
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Killer cell lectin-like receptor subfamily B member 1
Reactions:
Gene Name:	KLRB1
Uniprot ID:	Q12918
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Protein FAN
Reactions:
Gene Name:	NSMAF
Uniprot ID:	Q92636
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	LAG1 longevity assurance homolog 5
Reactions:
Gene Name:	LASS5
Uniprot ID:	Q8N5B7
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	ATP-binding cassette sub-family A member 7
Reactions:
Gene Name:	ABCA7
Uniprot ID:	Q8IZY2
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	GPI-anchor transamidase
Reactions:
Gene Name:	PIGK
Uniprot ID:	Q92643
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Glycosylphosphatidylinositol anchor attachment 1 protein
Reactions:
Gene Name:	GPAA1
Uniprot ID:	O43292
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Protein PLEKHA9
Reactions:
Gene Name:	PLEKHA9
Uniprot ID:	O95397
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Glycolipid transfer protein domain-containing protein 2
Reactions:
Gene Name:	GLTPD2
Uniprot ID:	A6NH11
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Putative uncharacterized protein PLEKHA8
Reactions:
Gene Name:	PLEKHA8
Uniprot ID:	B5MDU3
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	T-cell surface glycoprotein CD1a
Reactions:
Gene Name:	CD1A
Uniprot ID:	P06126
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Glycolipid transfer protein domain-containing protein 1
Reactions:
Gene Name:	GLTPD1
Uniprot ID:	Q5TA50
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	T-cell surface glycoprotein CD1c
Reactions:
Gene Name:	CD1C
Uniprot ID:	P29017
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Lipopolysaccharide-binding protein
Reactions:
Gene Name:	LBP
Uniprot ID:	P18428
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Putative uncharacterized protein DKFZp434L0435
Reactions:
Gene Name:	DKFZp434L0435
Uniprot ID:	Q9UFH6
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	T-cell surface glycoprotein CD1b
Reactions:
Gene Name:	CD1B
Uniprot ID:	P29016
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Glycolipid transfer protein
Reactions:
Gene Name:	GLTP
Uniprot ID:	Q9NZD2
Protein Sequence:	FASTA
Gene Sequence:	FASTA