Showing Compound Ceramide (FDB006397)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:07 UTC

Update date

2019-11-26 03:01:08 UTC

Primary ID

FDB006397

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ceramide

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) 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). Is key in the biosynthesis of glycosphingolipids and gangliosides. Ceramide is found in rice.

CAS Number

74713-60-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2S,3R,4E)-2-acylamino-1,3-Octadec-4-enediol	HMDB
(2S,3R,4E)-2-acylamino-1,3-octadec-4-enediol	biospider
(2S,3R,4E)-2-Acylaminooctadec-4-ene-1,3-diol	HMDB
(2S,3R,4E)-2-acylaminooctadec-4-ene-1,3-diol	biospider
C12-Ceramide	HMDB
Cer	HMDB
CER	biospider
Cer d18:1/12:0	HMDB
Cer(d18:1/12:0)	ChEBI
Cer(D18:1/12:0)	ChEBI

Showing 1 to 10 of 36 entries

Predicted Properties

Property	Value	Source
Water Solubility	7.9e-05 g/L	ALOGPS
logP	8.63	ALOGPS
logP	9.09	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	147.37 m³·mol⁻¹	ChemAxon
Polarizability	64.7 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C30H59NO3

IUPAC name

N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]dodecanamide

InChI Identifier

InChI=1S/C30H59NO3/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-29(33)28(27-32)31-30(34)26-24-22-20-17-12-10-8-6-4-2/h23,25,28-29,32-33H,3-22,24,26-27H2,1-2H3,(H,31,34)/b25-23+/t28-,29+/m0/s1

InChI Key

HXFPPRPLRSPNIB-VARSQMIESA-N

Isomeric SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCC

Average Molecular Weight

481.7944

Monoisotopic Molecular Weight

481.449494759

Classification

Description

Belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Ceramides

Direct Parent

Ceramides

Alternative Parents

Substituents

Ceramide
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acylsphingosine (CHEBI:72956 )
N-acylsphingosines (ceramides) (LMSP02010002 )

Ontology

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Poaceae

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Food and nutrition:

Biological role:

Modulator:

Insulin signaling antagonist

Molecular messenger:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Ceramide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-022i-5785598000-7031136168734e1ef5ee	Spectrum
Predicted GC-MS	Ceramide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2090000000-ae80000c40a296a1c5d8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2090000000-a13bd310025f03a29721	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2090000000-8d5084b0da3675b3f3f3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2090000000-d4824df02fcc2092417c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2090000000-f919f09dc660be85f13e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000900000-fe0f573db63b1b90fd2f	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0050900000-612b7fe1fb533df6232b	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-0090600000-9abebdbdb27db5a25cb2	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000900000-fa0543ff22d51d18b573	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0010900000-3de9968cb166260af69f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001k-0220900000-1f62f1430f619c4887d9	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000900000-2b1019f1dfd77202b1a5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000900000-2b1019f1dfd77202b1a5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0000900000-aa4c78e902645a2bb092	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000900000-5acec5af0818f408e044	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0050900000-f3ad47a5043cb0aa6c70	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-0090600000-797db203768da46183b0	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4446675

ChEMBL ID

Not Available

KEGG Compound ID

C00195

Pubchem Compound ID

5283562

Pubchem Substance ID

Not Available

ChEBI ID

16197

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04947

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

CERAMIDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Cer

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
2-hydroxyacylsphingosine 1-beta-galactosyltransferase	UGT8	Q16880
Acid ceramidase	ASAH1	Q13510
Alkaline ceramidase 1	ACER1	Q8TDN7
Alkaline ceramidase 2	ACER2	Q5QJU3
Antigen-presenting glycoprotein CD1d	CD1D	P15813
Beta-1,3-galactosyltransferase 5	B3GALT5	Q9Y2C3
Ceramide glucosyltransferase	UGCG	Q16739
Ceramide synthase 1	CERS1	P27544
Collagen type IV alpha-3-binding protein	COL4A3BP	Q9Y5P4
Epididymal secretory protein E1	NPC2	P61916