Structure Database (LMSD)
Common Name
C16 Sphingosine
Systematic Name
Hexadecasphing-4E-enine
Synonyms
- Hexadecasphingosine
LM ID
LMSP01040008
Formula
Exact Mass
Calculate m/z
271.251129
Sum Composition
Status
Curated
3D model of C16 Sphingosine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Sphingosine (d16:1) is an atypical sphingolipid formed by a series of enzymatic steps beginning with the condensation of myristoyl-CoA and serine via serine palmitoyltransferase long-chain base subunit 3 (SPTLC3), an SPT subunit that prefers myristoyl-CoA over palmitoyl-CoA.1,2 Sphingosine d16:1 is present in its free form at low levels in human plasma and as the sphingoid base in a variety of plasma sphingolipid species, including sphingosine-1-phosphate, ceramides, and sphingomyelins, as well as brain cerebrosides, at lower levels compared with the typical d18:1 sphingoid base.3,4,5,6 Sphingosine (d16:1) inhibits PKC in a mixed micelle activity assay.7 It reduces the production of superoxide induced by phorbol 12-myristate 13-acetate (PMA) in isolated human neutrophils and reduces the growth of CHO cells (IC50s = 1 and 3.2 µM, respectively). Plasma levels of sphingolipids containing sphingosine (d16:1) are associated with dietary intake of saturated fatty acids and protein in ethnic Chinese individuals.3 Plasma levels of sphingolipids containing sphingosine (d16:1) are decreased in patients with type 2 diabetes.8
This information has been provided by Cayman Chemical
References
1. 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).
3. Hornemann, T., Penno, A., Rütti, M.F., et al. The SPTLC3 subunit of serine palmitoyltransferase generates short chain sphingoid bases. The Journal of Biological Chemisty 284(39), 26322-26330 (2009).
4. Lai, M.K.P., Chew, W.S., Torta, F., et al. Biological effects of naturally occurring sphingolipids, uncommon variants, and their analogs. Neuromolecular Med. 18(3), 396-414 (2016).
7. Quehenberger, O., Armando, A.M., Brown, A.H., et al. Lipidomics reveals a remarkable diversity of lipids in human plasma. J. Lipid Res. 51(11), 3299-3305 (2010).
String Representations
InChiKey (Click to copy)
BTUSGZZCQZACPT-YYZTVXDQSA-N
InChi (Click to copy)
InChI=1S/C16H33NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-16(19)15(17)14-18/h12-13,15-16,18-19H,2-11,14,17H2,1H3/b13-12+/t15-,16+/m0/s1
SMILES (Click to copy)
OC[C@]([H])(N)[C@]([H])(O)/C=C/CCCCCCCCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
19
Rings
0
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
311.30
Topological Polar Surface Area
66.48
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
2
logP
4.00
Molar Refractivity
83.57
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Updated at
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