Structure Database (LMSD)

Common Name
C14 sphingosine
Systematic Name
tetradecasphing-4E-enine
Synonyms
  • (4E,d14:1) sphingosine
LM ID
LMSP01040006
Formula
C14H29NO2
Exact Mass
Calculate m/z
243.219829
Sum Composition
SPB 14:1;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Sphingoid bases [SP01]
Sphingoid base homologs and variants [SP0104]

Biological Context

Sphingosine (d14:1) is a bioactive sphingolipid that has been found in B. mori (silkworm), P. clarkii (crayfish), and A. aurita (jellyfish) extracts.1,2,3 It increases the germination rate of N. rileyi, an entomopathogenic fungus, with an EC50 value of 0.0102 ng/ml.1 Sphingosine (d14:1) inhibits protein kinase C (PKC) in vitro (IC50 = 7.3 mol%) as well as superoxide generation induced by phorbol 12-myristate 13-acetate (PMA) in neutrophils and reduces growth of CHO cells (IC50s = 19 and 8 μM, respectively).4 [Matreya, LLC. Catalog No. 1833]

This information has been provided by Cayman Chemical

References

1. Kariotoglou, D.M., and Mastronicolis, S.K. Sphingophosphonolipids, phospholipids, and fatty acids from Aegean jellyfish Aurelia aurita. Lipids 36(11), 1255-1264 (2001).
2. Moscatelli, E.A., and Gilliland, K.M. Sphingosine, a novel sphingosine base from Procambarus clarkii. Lipids 4(3), 244-245 (1969).
3. Noda, T., Ono, M., Iimure, K., et al. Characterization of a germination-accelerating factor from the silkworm (Bombyx mori Linnaeus) of entomopathogenic fungus Nomuraea rileyi (Farlow) Samson. Biosci. Biotech. Biochem. 74(6), 1226-1230 (2010).
4. Merrill, A.H., Jr., Nimkar, S., Menaldino, D., et al. Structural requirements for long-chain (shingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds. Biochemistry 28(8), 3138-3145 (1989).

String Representations

InChiKey (Click to copy)
VDRZDTXJMRRVMF-NXFSIWHZSA-N
InChi (Click to copy)
InChI=1S/C14H29NO2/c1-2-3-4-5-6-7-8-9-10-11-14(17)13(15)12-16/h10-11,13-14,16-17H,2-9,12,15H2,1H3/b11-10+/t13-,14+/m0/s1
SMILES (Click to copy)
C([C@H](N)[C@H](O)/C=C/CCCCCCCCC)O

Other Databases

CHEBI ID
83706
PubChem CID
42608342
Cayman ID
24373

Calculated Physicochemical Properties

Heavy Atoms 17
Rings 0
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 276.70
Topological Polar Surface Area 66.48
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 2
logP 3.22
Molar Refractivity 74.33

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