Structure Database (LMSD)

Common Name
Safingol ( L-threo-sphinganine)
Systematic Name
2S-aminooctadecane-1,3R-diol
Synonyms
LM ID
LMSP01080055
Formula
C18H39NO2
Exact Mass
Calculate m/z
301.298079
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Sphingoid bases [SP01]
Sphingoid base analogs [SP0108]

Biological Context

Safingol is the L-threo diastereomer of D-erythro-sphinganine and a dual inhibitor of PKC and sphingosine kinase (SPHK).1,2 It inhibits PKC by binding at the regulatory phorbol-binding domain (IC50 = 24 µM).1 Safingol also inhibits SPHK (Ki = ~5 µM).2 Safingol (0.2-6 µM) restores sensitivity to cisplatin in resistant AGScis5 cells and N87 gastric cancer cells in a concentration-dependent manner.3 [Matreya, LLC. Catalog No. 1807]

This information has been provided by Cayman Chemical

References

1. Baek, D.J., Macritchie, N., Anthony, N.G., et al. Structure-activity relationships and molecular modeling of sphingosine kinase inhibitors. J. Med. Chem. 56(22), 9310-9327 (2013).
2. Matula, K., Collie-Dugid, E., Murray, G., et al. Regulation of cellular sphingosine-1-phosphate by sphingosine kinase 1 and sphingosine-1-phopshate lyase determines chemotherapy resistance in gastroesophageal cancer. BMC Cancer 15:762, (2015).
3. Wilson, E., Olcott, M.C., Bell, R.M., et al. Inhibition of the oxidative burst in human neutrophils by sphingoid long-chain bases. Role of protein kinase C in activation of the burst. The Journal of Biological Chemisty 261(27), 12616-12623 (1986).

String Representations

InChiKey (Click to copy)
OTKJDMGTUTTYMP-ROUUACIJSA-N
InChi (Click to copy)
InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18-/m0/s1
SMILES (Click to copy)
OC[C@]([H])(N)[C@@]([H])(O)CCCCCCCCCCCCCCC

Other Databases

Wikipedia
Safingol
CHEBI ID
179060
PubChem CID
3058739
Cayman ID
18624

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 348.54
Topological Polar Surface Area 66.48
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 2
logP 5.01
Molar Refractivity 92.89

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Updated at
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