U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H37NO2
Molecular Weight 299.4919
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ERYTHRO-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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
http://www.uniprot.org/uniprot/W0FXB0
2
Target ID: http://www.uniprot.org/uniprot/W0FXB0
Inhibitor
8297
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
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes.
1989 Aug
A novel mechanism of action of corticotropin releasing factor in rat Leydig cells.
1990 Feb 5
Protein kinase C and platelet inhibition by D-erythro-sphingosine: comparison with N,N-dimethylsphingosine and commercial preparation.
1990 Oct 30
Ursodeoxycholic acid enhances glucocorticoid-induced tyrosine aminotransferase-gene expression in cultured rat hepatocytes.
1997 Nov 26
Activation of the melastatin-related cation channel TRPM3 by D-erythro-sphingosine [corrected].
2005 Mar
Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels.
2013 Mar
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 Sat Dec 16 01:34:35 GMT 2023
Edited
by admin
on Sat Dec 16 01:34:35 GMT 2023
Record UNII
0Y6SVQ612Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERYTHRO-SPHINGOSINE, (±)-
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (E)-DL-ERYTHRO-
Common Name English
DL-ERYTHRO-SPHINGOSINE [MI]
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (2R,3S,4E)-REL-
Common Name English
DL-ERYTHRO-SPHINGOSINE
MI  
Common Name English
C18-ERYTHRO-SPHINGENINE
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (R*,S*-(E))-(±)-
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (R*,S*-(E))-
Common Name English
ERYTHRO-DL-SPHINGOSINE
Common Name English
Code System Code Type Description
CAS
2733-29-1
Created by admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
PRIMARY
MERCK INDEX
m10144
Created by admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
PRIMARY Merck Index
FDA UNII
0Y6SVQ612Q
Created by admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
PRIMARY
PUBCHEM
5280335
Created by admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
PRIMARY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966