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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H37NO2
Molecular Weight 299.4919
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SPHINGOSINE

SMILES

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

InChI

InChIKey=WWUZIQQURGPMPG-KRWOKUGFSA-N
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+/t17-,18+/m0/s1

HIDE SMILES / InChI
Molecular Formula C18H37NO2
Molecular Weight 299.4919
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Sphingosine harbors two chiral centers and therefore exhibits four stereoisomers, only one of which, the D-erythro (2S,3R) is known to exist naturally. ERYTHRO-SPHINGOSINE, (±)- is a mixture of two isomers: inactive ERYTHRO-SPHINGOSINE, (+)- and the active ERYTHRO-SPHINGOSINE, (-), also known as D-erythro (2S,3R)-SPHINGOSINE or D-erythro –SPHINGOSINE. It was found, that D-erythro –SPHINGOSINE acts as a potent inhibitor of protein kinase C and of transient receptor potential melastatin 7 (TRPM7). Besides, was shown, that sphingosine may be efficacious against alveolar rhabdomyosarcoma, irrespective of TP53 mutation status. It also could evolve as alternative treatment options for aggressive lymphomas via PKC inhibition, apoptosis, and autophagy.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
http://www.uniprot.org/uniprot/W0FXB0
2
Target ID: http://www.uniprot.org/uniprot/W0FXB0
Inhibitor
8504
Transient receptor potential cation channel subfamily M member 7
6
Target ID: Q96QT4
Gene ID: 54822.0
Gene Symbol: TRPM7
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels.
2013-03
Pharmacologic manipulation of sphingosine kinase in retinal endothelial cells: implications for angiogenic ocular diseases.
2006-11
Activation of the melastatin-related cation channel TRPM3 by D-erythro-sphingosine [corrected].
2005-03
ACTH regulates steroidogenic gene expression and cortisol biosynthesis in the human adrenal cortex via sphingolipid metabolism.
2004-11
Modulation by sphingosine of phosphorylation of substrate proteins by protein kinase C in nuclei from cow mammary gland.
2004-10
Inhibition of arachidonic acid release and cytosolic phospholipase A2 alpha activity by D-erythro-sphingosine.
2004-01-19
Role of human sphingosine-1-phosphate phosphatase 1 in the regulation of intra- and extracellular sphingosine-1-phosphate levels and cell viability.
2003-09-05
Sphingosine in apoptosis signaling.
2002-12-30
Ursodeoxycholic acid enhances glucocorticoid-induced tyrosine aminotransferase-gene expression in cultured rat hepatocytes.
1997-11-26
Use of D-erythro-sphingosine as a pharmacological inhibitor of protein kinase C in human platelets.
1991-09-01
Protein kinase C and platelet inhibition by D-erythro-sphingosine: comparison with N,N-dimethylsphingosine and commercial preparation.
1990-10-30
A novel mechanism of action of corticotropin releasing factor in rat Leydig cells.
1990-02-05
A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes.
1989-08
Patents

Patents

CN103992985A
2
JP1016708A
2
JP2000026271A
2
JP2000109409A
2
JP2000125887A
2
JP2000191496A
2
JP2000256188A
2
JP2001039859A
3
JP2001057890A
2
JP2001064150A
3
JP2001078712A
2
JP2001158735A
2
JP2001158736A
2
JP2001213858A
2
JP2002243737A
2
JP2002326920A
3
JP2002510320A
4
JP2002533379A
53
JP2002544135A
4
JP2002544218A
14
JP2003171229A
2
JP2003171269A
2
JP2003192525A
2
JP2003221369A
2
JP2003252765A
2
JP2003261794A
2
JP2003321393A
7
JP2004196665A
6
JP2004196666A
4
JP2004231616A
2
JP2004256471A
3
JP2004269374A
2
JP2004331594A
2
JP2005002016A
2
JP2005002017A
2
JP2005002018A
2
JP2005002019A
2
JP2005002020A
2
JP2005002021A
2
JP2005002022A
2
JP2005002023A
2
JP2005023068A
2
JP2005220030A
2
JP2005220031A
2
JP2005295994A
2
JP2005529879A
4
JP2005531285A
2
JP2006028196A
2
JP2006045113A
3
JP2006062968A
2
JP2006257069A
2
JP2006515309A
16

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Exogenous addition of D-erythro-sphingosine inhibited the responses in a concentration-dependent manner in the two cell lines: PC12 and L929. D-erythro-sphingosine significantly inhibited mastoparan-, but not Na3VO4-, stimulated arachidonic acid release in PC12 cells. D-erythro-S1P showed no effect on the responses. Production of prostaglandin F2alpha was suppressed by D-erythro-sphingosine (10 microM) in PC12 cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:56:35 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:35 GMT 2025
Record UNII
NGZ37HRE42
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(-)-D-ERYTHRO-SPHINGOSINE
Preferred Name English
SPHINGOSINE
MI  
Systematic Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (2S,3R,4E)-
Systematic Name English
(2S,3R)-SPHINGOSINE
Systematic Name English
ERYTHRO-4-SPHINGENINE
Common Name English
D-SPHINGOSINE
Common Name English
(-)-SPHINGOSINE
Systematic Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (E)-D-ERYTHRO-
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (R-(R*,S*-(E)))-
Common Name English
SPHINGENINE
Common Name English
C18-SPHINGOSINE
Common Name English
(4E)-SPHINGENINE
Common Name English
4-TRANS-SPHINGENINE
Common Name English
4-SPHINGENINE
Common Name English
(2S,3R,4E)-2-AMINO-4-OCTADECENE-1,3-DIOL
Systematic Name English
SPHINGOSINE [MI]
Common Name English
Code System Code Type Description
CHEBI
16393
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID90861763
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
FDA UNII
NGZ37HRE42
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
MESH
D013110
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
WIKIPEDIA
SPHINGOSINE
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
PUBCHEM
5280335
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
CHEBI
26743
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
DRUG BANK
DB03203
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
CAS
123-78-4
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
MERCK INDEX
m10144
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
204-651-3
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
CHEBI
45719
Created by admin on Mon Mar 31 17:56:35 GMT 2025 , Edited by admin on Mon Mar 31 17:56:35 GMT 2025
PRIMARY
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DERIVATIVE -> PARENT
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Structure of SPHINGOSINE 1-PHOSPHATE
METABOLITE -> PARENT
NIH
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