Bovine Metabolome Database: Showing metabocard for Galactosylceramide (d18:1/16:0) (BMDB0010708)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:12:16 UTC

Update Date

2020-05-21 16:28:59 UTC

BMDB ID

BMDB0010708

Secondary Accession Numbers

BMDB10708

Metabolite Identification

Common Name

Galactosylceramide (d18:1/16:0)

Description

Galactosylceramide (d18:1/16:0), also known as a-galcer or cerebroside, belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. Galactosylceramide (d18:1/16:0) is an extremely weak basic (essentially neutral) compound (based on its pKa). Galactosylceramide (d18:1/16:0) is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
a-GalCer	HMDB
alpha-GalCer	HMDB
Cerebroside	HMDB
D-Galactosyl-N-acylsphingosine	HMDB
D-Galactosylceramide	HMDB
delta-Galactosyl-N-acylsphingosine	HMDB
delta-Galactosylceramide	HMDB
Gal-b-cer	HMDB
Gal-beta-1-1'cer	HMDB
Gal-beta-cer	HMDB
Galactocerebroside	HMDB
Galactosylceramide	HMDB
GalCer	HMDB
N-(Hexadecanoyl)-1-b-galactosyl-sphing-4-enine	HMDB
N-(Hexadecanoyl)-1-beta-galactosyl-sphing-4-enine	HMDB

Chemical Formula

C₄₀H₇₇NO₈

Average Molecular Weight

700.0413

Monoisotopic Molecular Weight

699.564918445

IUPAC Name

N-[(4Z)-3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexadecanamide

Traditional Name

N-[(4Z)-3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexadecanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)NC(CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)\C=C/CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C40H77NO8/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(43)33(32-48-40-39(47)38(46)37(45)35(31-42)49-40)41-36(44)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,33-35,37-40,42-43,45-47H,3-26,28,30-32H2,1-2H3,(H,41,44)/b29-27-/t33?,34?,35-,37+,38+,39-,40-/m1/s1

InChI Key

VJLLLMIZEJJZTE-DQVPDRNHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosyl-N-acylsphingosines

Alternative Parents

Substituents

Glycosyl-n-acylsphingosine
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty amide
Fatty acyl
Monosaccharide
N-acyl-amine
Oxane
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Carbonyl group
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endosome
Membrane
Mitochondria

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
logP	7.7	ALOGPS
logP	9.09	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	0.019	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	148.71 Å²	ChemAxon
Rotatable Bond Count	33	ChemAxon
Refractivity	198.19 m³·mol⁻¹	ChemAxon
Polarizability	87.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0030009000-1282a249578ef3221467	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0030009010-332e724e00f7ab11142c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gx0-0100659300-d2cbd2dd6da8dbaa9059	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-0350493000-0868daf2869165821a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dm-3980230000-15ecbee9ee334060b380	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1300259000-2ac083e72ea2f4fd8e25	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03gi-4930455000-644c996c644cb72ca5ac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9331000000-e833827c8f7d7ca3c897	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-3100095800-caef332a980acf7e4187	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-2220193200-c8dd5cfe42a5062a250d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-7191210000-3f1adb45d7f91a2684b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000009000-2978eacc43b2095a745c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-3100139000-c6d87f301eff13e5888d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052k-8293300000-a386569d1b8551f01a57	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endosome
Membrane
Mitochondria

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Sphingolipid Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0010708

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027858

KNApSAcK ID

Not Available

Chemspider ID

24765744

KEGG Compound ID

C02686

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53480652

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

Enzyme Details

1. Galactosylceramide sulfotransferase

General function:: Involved in galactosylceramide sulfotransferase activity
Specific function:: Catalyzes the sulfation of membrane glycolipids. Seems to prefer beta-glycosides at the non-reducing termini of sugar chains attached to a lipid moiety. Catalyzes the synthesis of HSO3-3-galactosylceramide (sulfatide), a major lipid component of the myelin sheath and of HSO3-3-monogalactosylalkylacylglycerol (seminolipid), present in spermatocytes. Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro) (By similarity).
Gene Name:: GAL3ST1
Uniprot ID:: A6QNK1
Molecular weight:: 48754.0

Reactions

Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate → 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate	details

Enzyme Details

2. Arylsulfatase A

General function:: Inorganic ion transport and metabolism
Specific function:: Hydrolyzes cerebroside sulfate.
Gene Name:: ARSA
Uniprot ID:: Q08DD1
Molecular weight:: 53807.0

Reactions

3-O-Sulfogalactosylceramide (d18:1/24:0) + Water → Galactosylceramide (d18:1/16:0) + Sulfate	details

Enzyme Details

3. UDP-glucuronosyltransferase 3A1

General function:: Carbohydrate transport and metabolism
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
Gene Name:: UGT3A1
Uniprot ID:: Q1LZI1
Molecular weight:: 59682.0

Reactions

Ceramide (d18:1/18:0) → Galactosylceramide (d18:1/16:0)	details

Enzyme Details

4. Alpha-N-acetylgalactosaminidase

General function:: Not Available
Specific function:: Removes terminal alpha-N-acetylgalactosamine residues from glycolipids and glycopeptides. Required for the breakdown of glycolipids (By similarity).
Gene Name:: NAGA
Uniprot ID:: Q58DH9
Molecular weight:: 46533.0

Reactions

Galactosylceramide (d18:1/16:0) + D-Galactose → Galabiosylceramide (d18:1/22:0)	details

Enzyme Details

5. Galactosylceramidase

General function:: Not Available
Specific function:: Not Available
Gene Name:: GALC
Uniprot ID:: E1B7K0
Molecular weight:: 77833.0

Reactions

Galactosylceramide (d18:1/16:0) → Ceramide (d18:1/18:0)	details

Showing metabocard for Galactosylceramide (d18:1/16:0) (BMDB0010708)

Structure for BMDB0010708 (Galactosylceramide (d18:1/16:0))

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions