Showing Compound N-Palmitoylsphingosine (FDB022245)

Record Information

Version

1.0

Creation date

2011-09-21 00:10:48 UTC

Update date

2015-07-21 06:57:05 UTC

Primary ID

FDB022245

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-Palmitoylsphingosine

Description

N-Palmitoylsphingosine 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. Based on a literature review a significant number of articles have been published on N-Palmitoylsphingosine.

CAS Number

24696-26-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
[R-[R,S-(E)]]-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-Hexadecanamide	hmdb
D-erythro-C16-Ceramide	hmdb
D-erythro-D4-Ceramide	hmdb
N-Palmitoyl 4-sphingenine	hmdb
N-Palmitoyl-D-sphingosine	hmdb
N-Palmitoylsphingosine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	4.1e-05 g/L	ALOGPS
logP	9.49	ALOGPS
logP	10.87	ChemAxon
logS	-7.1	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	30	ChemAxon
Refractivity	165.78 m³·mol⁻¹	ChemAxon
Polarizability	73.13 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

C34H67NO3

IUPAC name

N-(1,3-dihydroxyoctadec-4-en-2-yl)hexadecanamide

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)

InChI Key

YDNKGFDKKRUKPY-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C=CCCCCCCCCCCCCC

Average Molecular Weight

537.9007

Monoisotopic Molecular Weight

537.512095015

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

a ceramide (CPD66-41 )

Ontology

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Blood

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Role

Industrial application:

Food and nutrition:

Biological role:

Modulator:

Insulin signaling antagonist

Molecular messenger:

Signaling molecule

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	N-Palmitoylsphingosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0300-4214179000-7ee0697a6268203e693f	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000090000-f294f0ced8f149249815	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-0050090000-80f4b14827e42ec58fea	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03l0-0090050000-c9f32bf831226119babd	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000090000-876883608819d763f04e	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-0050090000-22ff2434faf08fcef599	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03l0-0090050000-e6a7f6704ac5e854065c	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000090000-d2d11b266d3c5c7e73ff	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000090000-d2d11b266d3c5c7e73ff	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0000190000-6ce0a8c6d5140383d837	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000090000-15b6716e7356e06043b6	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0010090000-e14e9c0c2e28b7a12b19	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ue0-0040090000-a44d6a95bf21d0975da6	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4510097

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5353456

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00790

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

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

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Acid ceramidase	ASAH1	Q13510
Putative neutral ceramidase C	ASAH2C	P0C7U2
Alkaline ceramidase 2	ACER2	Q5QJU3
Neutral ceramidase	ASAH2	Q9NR71
Alkaline ceramidase 1	ACER1	Q8TDN7
Phosphatidylcholine:ceramide cholinephosphotransferase 2	SGMS2	Q8NHU3
Phosphatidylcholine:ceramide cholinephosphotransferase 1	SGMS1	Q86VZ5
Ganglioside GM2 activator	GM2A	P17900
Sphingosine-1-phosphate lyase 1	SGPL1	O95470
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase	PIGL	Q9Y2B2
Sphingomyelin phosphodiesterase	SMPD1	P17405
Ceramide glucosyltransferase	UGCG	Q16739
Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q	PIGQ	Q9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit A	PIGA	P37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit H	PIGH	Q14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit P	PIGP	P57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit C	PIGC	Q92535
2-hydroxyacylsphingosine 1-beta-galactosyltransferase	UGT8	Q16880
Collagen type IV alpha-3-binding protein	COL4A3BP	Q9Y5P4
T-cell surface glycoprotein CD1e, membrane-associated	CD1E	P15812
Epididymal secretory protein E1	NPC2	P61916
Ceramide synthase 1	CERS1	P27544
Antigen-presenting glycoprotein CD1d	CD1D	P15813
GPI mannosyltransferase 1	PIGM	Q9H3S5
Phosphatidylinositol-glycan biosynthesis class W protein	PIGW	Q7Z7B1
Phosphatidylinositol-glycan biosynthesis class X protein	PIGX	Q8TBF5
GPI mannosyltransferase 4	PIGZ	Q86VD9
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase	B3GNT5	Q9BYG0
Beta-1,3-galactosyltransferase 5	B3GALT5	Q9Y2C3
GPI mannosyltransferase 3	PIGB	Q92521
Phosphatidylinositol-glycan biosynthesis class F protein	PIGF	Q07326
GPI ethanolamine phosphate transferase 2	PIGG	Q5H8A4
GPI ethanolamine phosphate transferase 1	PIGN	O95427
GPI ethanolamine phosphate transferase 3	PIGO	Q8TEQ8
GPI transamidase component PIG-S	PIGS	Q96S52
GPI transamidase component PIG-T	PIGT	Q969N2
Phosphatidylinositol glycan anchor biosynthesis class U protein	PIGU	Q9H490
GPI mannosyltransferase 2	PIGV	Q9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y	PIGY	Q3MUY2
Non-lysosomal glucosylceramidase	GBA2	Q9HCG7
Protein FAN	NSMAF	Q92636
GPI-anchor transamidase	PIGK	Q92643