Showing Compound Sphingosine (FDB021919)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:10 UTC

Update date

2019-11-26 03:21:00 UTC

Primary ID

FDB021919

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Sphingosine

Description

A 18-carbon amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. (Dorland, 28th ed.) Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid. [HMDB]. Sphingosine is found in many foods, some of which are alaska blueberry, watercress, redcurrant, and rowanberry.

CAS Number

123-78-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(-)-D-Erythro-sphingosine	HMDB
(-)-D-erythro-Sphingosine	hmdb
(2S,3R)-Sphingosine	HMDB
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol	HMDB
(4E)-Sphingenine	HMDB
4-Sphingenine	HMDB
4-trans-Sphingenine	HMDB
[R-[R,s-(e)]]-2-amino-4-octadecene-1,3-diol	HMDB
[R-[R,S-(E)]]-2-amino-4-Octadecene-1,3-diol	hmdb

Showing 1 to 9 of 9 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0039 g/L	ALOGPS
logP	5.15	ALOGPS
logP	4.57	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.89 m³·mol⁻¹	ChemAxon
Polarizability	39.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H37NO2

IUPAC name

(4E)-2-aminooctadec-4-ene-1,3-diol

InChI Identifier

InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+

InChI Key

WWUZIQQURGPMPG-CCEZHUSRSA-N

Isomeric SMILES

CCCCCCCCCCCCC\C=C\C(O)C(N)CO

Average Molecular Weight

299.4919

Monoisotopic Molecular Weight

299.282429433

Classification

Description

Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,2-aminoalcohols

Alternative Parents

Substituents

Secondary alcohol
1,2-aminoalcohol
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Primary aliphatic amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

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	Sphingosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dr-9260000000-2ff04e0afd9e8b2f0851	Spectrum
Predicted GC-MS	Sphingosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-003r-8915100000-51f94df9cbd9e00dbf76	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0090000000-67307f0b7f6f858af400	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-9010000000-e66065dfabaedfa9a7f2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0api-9000000000-a5c7c01555839f61ab3d	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0092000000-c0188d9e3166e42d0a72	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02ai-2390000000-23fd78f38dca1695f653	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-6940000000-bd71a7546dbbc9a6e83b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-310f8ec2f529dd63e5b7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07d4-4090000000-3ec929924c6bbc7293e0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9030000000-c344fe4fe9af07abf710	2016-09-12	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum

External Links

ChemSpider ID

4510275

ChEMBL ID

Not Available

KEGG Compound ID

C00319

Pubchem Compound ID

5353955

Pubchem Substance ID

Not Available

ChEBI ID

16393

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00252

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34606

KNApSAcK ID

Not Available

HET ID

1SX6

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Sphingosine

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
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 synthase 1	CERS1	P27544
Epididymal secretory protein E1	NPC2	P61916
Ganglioside GM2 activator	GM2A	P17900
GPI ethanolamine phosphate transferase 1	PIGN	O95427
GPI ethanolamine phosphate transferase 2	PIGG	Q5H8A4