Structure Database (LMSD)

Common Name
C17 Sphinganine
Systematic Name
heptadecasphinganine
Synonyms
LM ID
LMSP01040003
Formula
C17H37NO2
Exact Mass
Calculate m/z
287.282429
Sum Composition
SPB 17:0;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

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

Biological Context

Sphinganine (d17:0) is a synthetic bioactive sphingolipid.1 It is active against C. glabrata and C. albicans with a minimum fungicidal concentration (MFC) value of 0.5 µg/ml for both. Sphinganine (d17:0) has commonly been used as an internal standard for the detection of sphingolipids in chromatographic and mass spectrometry applications.2,3

This information has been provided by Cayman Chemical

References

1. Thevissen, K., Hillaert, U., Meert, E.M., et al. Fungicidal activity of truncated analogues of dihydrosphingosine. Bioorg. Med. Chem. Lett. 18(13), 3728-3730 (2008).
2. Spassieva, S., Bielawski, J., Anelli, V., et al. Combination of C17 sphingoid base homologues and mass spectrometry analysis as a new approach to study sphingolipid metabolism. Methods Enzymol. 434, 233-241 (2007).
3. Qu, F., Wu, C.S., Hou, J.F., et al. Sphingolipids as new biomarkers for assessment of delayed-type hypersensitivity and response to triptolide. PLoS One 7(12), e52454 (2012).

String Representations

InChiKey (Click to copy)
KFQUQCFJDMSIJF-DLBZAZTESA-N
InChi (Click to copy)
InChI=1S/C17H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)16(18)15-19/h16-17,19-20H,2-15,18H2,1H3/t16-,17+/m0/s1
SMILES (Click to copy)
OC[C@]([H])(N)[C@]([H])(O)CCCCCCCCCCCCCC

Other Databases

CHEBI ID
137124
PubChem CID
3247037
Cayman ID
22510
Avanti ID
LM2001

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 331.24
Topological Polar Surface Area 66.48
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 2
logP 4.62
Molar Refractivity 88.28

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Updated at
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