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Compound Detail

CHEMBL322333

DIMETHYLSPINGOSINE
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CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL322333
Name DIMETHYLSPINGOSINE
Phase Preclinical
Structure Type MOL
InChI Key YRXOQXUDKDCXME-YIVRLKKSSA-N
4
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

327.6
MW (Da)
4.53
ALogP
3
HBA
2
HBD
43.7
PSA (Ų)
0.32
QED
0
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H41NO2
MW 327.55
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness 1.10

Activity Summary

IC50 11 meas. best 6.1
Ki 6 meas. best 5.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
FL5.12
CHEMBL4296414
 IC50 6.1 6.1 800.0 1
Sphingosine kinase 1
CHEMBL4394
 IC50 5.66 4.8517 2170.0 6
Lethal factor
CHEMBL4372
 IC50 5.64 5.64 2300.0 1
Sphingosine kinase 1
CHEMBL4394
 Ki 5.3 5.1067 5000.0 3
Sphingosine kinase 2
CHEMBL3023
 Ki 4.92 4.89 12000.0 3
Sphingosine kinase 2
CHEMBL3023
 IC50 4.79 4.69 16300.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
FL5.12 IC50 = 800.0 nM 6.1 Cytotoxicity against mouse FL5.12A cells after 48 hrs by DAPI staining-based flo... 27475534
Sphingosine kinase 1 IC50 = 2170.0 nM 5.66 Inhibition of SphK1 19467599
Lethal factor IC50 = 2300.0 nM 5.64 Protection against Bacillus anthracis lethal toxin-mediated cytotoxicity in mous... 17485504
Sphingosine kinase 1 Ki = 5000.0 nM 5.3 Inhibition of SphK1 (unknown origin) 24471412
Sphingosine kinase 1 IC50 = 5700.0 nM 5.24 Inhibition of EGFP-fused human SPHK1 expressed in CHO cells 19469544
Sphingosine kinase 1 IC50 = 5700.0 nM 5.24 Inhibition of human sphingosine kinase 1 by off chip mobility shift assay 19800228
Sphingosine kinase 1 Ki = 6000.0 nM 5.22 Inhibition of EGFP-fused human SPHK1 expressed in CHO cells using D-erythro-sphi... 19469544
Sphingosine kinase 2 Ki = 12000.0 nM 4.92 Inhibition of SphK2 (unknown origin) 24471412
Sphingosine kinase 2 Ki = 12500.0 nM 4.9 Inhibition of human cloned SPHK2 expressed in CHO cells using D-erythro-sphingos... 19469544
Sphingosine kinase 2 Ki = 14000.0 nM 4.85 Inhibition of His-tagged full length human recombinant SPHK2 expressed in baculo... 27255176
Sphingosine kinase 1 Ki = 16000.0 nM 4.8 Inhibition of His-tagged full length human recombinant SPHK1 expressed in baculo... 27255176
Sphingosine kinase 2 IC50 = 16300.0 nM 4.79 Inhibition of human recombinant SphK2 preincubated for 5 mins followed by substr... -
Sphingosine kinase 2 IC50 = 20000.0 nM 4.7 Inhibition of recombinant human SphK2 using NBD-sphingosine as substrate after 2... 28408190
Sphingosine kinase 2 IC50 = 26290.0 nM 4.58 Inhibition of GST-tagged full length human recombinant SPHK2 expressed in baculo... 27255176
Sphingosine kinase 1 IC50 = 35790.0 nM 4.45 Inhibition of human recombinant SphK1 preincubated for 5 mins followed by substr... -
Sphingosine kinase 1 IC50 = 50560.0 nM 4.3 Inhibition of GST-tagged full length human recombinant SPHK1 expressed in baculo... 27255176
Sphingosine kinase 1 IC50 = 60000.0 nM 4.22 Inhibition of recombinant human SphK1 using NBD-sphingosine as substrate after 2... 28408190

Literature References

PubMed DOI Target Context # Activities
19469544 10.1021/jm900121d Sphingosine kinase 1 5
19469544 10.1021/jm900121d Sphingosine kinase 2 4
27475534 10.1016/j.bmc.2016.07.038 FL5.12 3
19469544 10.1021/jm900121d U-937 2
21868240 10.1016/j.bmc.2011.07.061 Protein kinase C beta type 2
27255176 10.1016/j.bmc.2016.05.047 Sphingosine kinase 2 2
21868240 10.1016/j.bmc.2011.07.061 Protein kinase C eta type 2
27255176 10.1016/j.bmc.2016.05.047 Sphingosine kinase 1 2
17485504 10.1128/aac.01184-06 Lethal factor 2
17485504 10.1128/aac.01184-06 Unchecked 1
10560747 10.1016/s0960-894x(99)00554-5 Unchecked 1
19469544 10.1021/jm900121d Protein kinase C alpha type 1
19467599 10.1016/j.bmcl.2009.05.035 Sphingosine kinase 1 1
19467599 10.1016/j.bmcl.2009.05.035 Sphingosine kinase 2 1
19800228 10.1016/j.bmcl.2009.09.022 Sphingosine kinase 1 1
9644076 10.1021/np970527y Prorocentrum micans 1
21868240 10.1016/j.bmc.2011.07.061 Protein kinase C zeta type 1
21868240 10.1016/j.bmc.2011.07.061 Protein kinase C theta type 1
9644076 10.1021/np970527y Brachiomonas submarina 1
9644076 10.1021/np970527y Anagnostidinema amphibium 1

Data from ChEMBL 36 via Core Engine