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
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
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 |
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1898331 |
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Target ID: http://www.uniprot.org/uniprot/W0FXB0 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14729377 |
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Target ID: Q96QT4 Gene ID: 54822.0 Gene Symbol: TRPM7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23145923 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes. | 1989 Aug |
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A novel mechanism of action of corticotropin releasing factor in rat Leydig cells. | 1990 Feb 5 |
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Protein kinase C and platelet inhibition by D-erythro-sphingosine: comparison with N,N-dimethylsphingosine and commercial preparation. | 1990 Oct 30 |
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Use of D-erythro-sphingosine as a pharmacological inhibitor of protein kinase C in human platelets. | 1991 Sep 1 |
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Ursodeoxycholic acid enhances glucocorticoid-induced tyrosine aminotransferase-gene expression in cultured rat hepatocytes. | 1997 Nov 26 |
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Sphingosine in apoptosis signaling. | 2002 Dec 30 |
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Inhibition of arachidonic acid release and cytosolic phospholipase A2 alpha activity by D-erythro-sphingosine. | 2004 Jan 19 |
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Activation of the melastatin-related cation channel TRPM3 by D-erythro-sphingosine [corrected]. | 2005 Mar |
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Pharmacologic manipulation of sphingosine kinase in retinal endothelial cells: implications for angiogenic ocular diseases. | 2006 Nov |
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Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels. | 2013 Mar |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14729377
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
Edited
Fri Dec 15 15:24:16 UTC 2023
by
admin
on
Fri Dec 15 15:24:16 UTC 2023
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Record UNII |
NGZ37HRE42
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Record Status |
Validated (UNII)
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Record Version |
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