Compound Detail

CHEMBL67166

SPHINGOSINE

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CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL67166
Name	SPHINGOSINE
Phase	Preclinical
Structure Type	MOL
InChI Key	WWUZIQQURGPMPG-KRWOKUGFSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

299.5

MW (Da)

3.92

ALogP

HBA

HBD

66.5

PSA (Å²)

0.32

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C18H37NO2
MW	299.50
Aromatic Rings	0
Heavy Atoms	21
NP-Likeness	1.48

Activity Summary

IC50 21 meas. best 7.01

EC50 3 meas. best 5.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
cAMP-dependent protein kinase catalytic subunit alpha CHEMBL3390	IC50	7.01	7.01	98.0	1
Streptococcus sp. 'group A' CHEMBL612389	EC50	5.82	5.82	1519.0	1
Sphingosine kinase 2 CHEMBL3023	IC50	5.81	5.81	1560.0	1
Jurkat CHEMBL397	IC50	5.7	5.5425	2010.0	4
Streptokinase A CHEMBL1293228	EC50	5.59	5.59	2560.0	1
FL5.12 CHEMBL4296414	IC50	5.44	5.44	3600.0	1
Sphingosine kinase 1 CHEMBL4394	IC50	5.41	5.41	3860.0	1
Canis familiaris CHEMBL373	IC50	5.38	5.38	4200.0	1
Ubiquitin-conjugating enzyme E2 N CHEMBL6089	IC50	5.21	5.2	6200.0	2
Protein kinase C (PKC) CHEMBL2094266	IC50	5.17	4.745	6700.0	6
Streptococcus CHEMBL612313	EC50	5.09	5.09	8099.0	1
Cholesteryl ester transfer protein CHEMBL3572	IC50	4.94	4.94	11500.0	1
C-C chemokine receptor type 6 CHEMBL4423	IC50	4.68	4.68	20900.0	1
C-X-C chemokine receptor type 5 CHEMBL1075315	IC50	4.49	4.49	32494.0	1
Protein kinase C, PKC; classical CHEMBL2097168	IC50	4.24	4.24	57000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
cAMP-dependent protein kinase catalytic subunit alpha	IC50	=	98.0	nM	7.01	Inhibition of cAMP-dependent kinase PKA(Protein kinase A) catalytic subunit at 1...	1895309
Streptococcus sp. 'group A'	EC50	=	1519.0	nM	5.82	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden...	-
Sphingosine kinase 2	IC50	=	1560.0	nM	5.81	Inhibition of SphK2	19467599
Jurkat	IC50	=	2010.0	nM	5.7	Inhibition of wild type human Jurkat cells after 18 hrs by MTT assay	17400555
Streptokinase A	EC50	=	2560.0	nM	5.59	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden...	-
Jurkat	IC50	=	2880.0	nM	5.54	Inhibition of 2-amino-4-(4-heptyloxyphenyl)-2-methylbutanol-resistant human Jurk...	17400555
Jurkat	IC50	=	3380.0	nM	5.47	Inhibition of human 2-amino-4-(4-heptyloxyphenyl)-2-methylbutanol-resistant huma...	17400555
Jurkat	IC50	=	3480.0	nM	5.46	Inhibition of 2-amino-4-(4-heptyloxyphenyl)-2-methylbutanol-resistant human Jurk...	17400555
FL5.12	IC50	=	3600.0	nM	5.44	Cytotoxicity against mouse FL5.12A cells after 48 hrs by DAPI staining-based flo...	27475534
Sphingosine kinase 1	IC50	=	3860.0	nM	5.41	Inhibition of SphK1	19467599
Canis familiaris	IC50	=	4200.0	nM	5.38	Inhibition of PKC-dependent neutrophil superoxide burst in dogs	-
Ubiquitin-conjugating enzyme E2 N	IC50	=	6200.0	nM	5.21	PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS for the identification of U...	-
Ubiquitin-conjugating enzyme E2 N	IC50	=	6425.0	nM	5.19	PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS for the identification of U...	-
Protein kinase C (PKC)	IC50	=	6700.0	nM	5.17	Inhibitory concentration required against Protein kinase C (isolated from rat br...	-
Streptococcus	EC50	=	8099.0	nM	5.09	PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify...	-
Protein kinase C (PKC)	IC50	=	10000.0	nM	5.0	Inhibition of rat brain PKC	1874734
Cholesteryl ester transfer protein	IC50	=	11500.0	nM	4.94	Compound was measured for its inhibitory activity against cholesteryl ester tran...	-
C-C chemokine receptor type 6	IC50	=	20900.0	nM	4.68	PUBCHEM_BIOASSAY: SAR analysis of small molecule antagonists of the CCR6 recepto...	-
Protein kinase C (PKC)	IC50	=	23000.0	nM	4.64	Displacement of [3H]PDBU from protein kinase C	8289196
Protein kinase C (PKC)	IC50	=	23400.0	nM	4.63	Inhibition of Protein kinase C isolated from rat brain	-

Literature References

PubMed	DOI	Target Context	# Activities
19525967	10.1038/nchembio.191	Endoglycoceramidase II	42
12127527	10.1016/s0960-894x(02)00367-0	Nakaseomyces glabratus	10
17400555	10.1074/jbc.m609124200	Jurkat	7
19525967	10.1038/nchembio.191	Unchecked	3
27475534	10.1016/j.bmc.2016.07.038	FL5.12	3
-	10.1016/S0960-894X(00)80600-9	NON-PROTEIN TARGET	3
18778047	10.1021/jm800345u	Staphylococcus aureus	2
-	10.1016/0960-894X(95)00428-V	Mus musculus	2
10636242	10.1016/s0960-894x(99)00574-0	Leukemia 60 cell line	2
8289196	10.1021/jm00027a025	Protein kinase C (PKC)	2
-	10.1016/0960-894X(95)00427-U	Protein kinase C (PKC)	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
9644076	10.1021/np970527y	Ulva	2
1895309	10.1021/jm00113a038	Protein kinase C, PKC; classical	1
9644076	10.1021/np970527y	Brachiomonas submarina	1
9644076	10.1021/np970527y	Anagnostidinema amphibium	1
17070046	10.1016/j.bmcl.2006.10.014	Sphingosine kinase 2	1
17070046	10.1016/j.bmcl.2006.10.014	Sphingosine kinase 1	1
1895309	10.1021/jm00113a038	cAMP-dependent protein kinase catalytic subunit alpha	1
-	10.1016/0960-894X(95)00427-U	Mus musculus	1

Data from ChEMBL 36 via Core Engine