Sphingosine

Details

• Internal ID: 9a7d629c-6390-4be7-b641-c1f4d0574534
• Taxonomy: Organic nitrogen compounds > Organonitrogen compounds > Amines > Alkanolamines > 1,2-aminoalcohols
• IUPAC Name: (E,2S,3R)-2-aminooctadec-4-ene-1,3-diol
• SMILES (Canonical): CCCCCCCCCCCCCC=CC(C(CO)N)O
• SMILES (Isomeric): CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
• InChI: InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
• InChI Key: WWUZIQQURGPMPG-KRWOKUGFSA-N
• Popularity: 12,306 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₇NO₂
• Molecular Weight: 299.50 g/mol
• Exact Mass: 299.282429423 g/mol
• Topological Polar Surface Area (TPSA): 66.50 Ų
• XlogP: 5.30

Synonyms

• D-erythro-Sphingosine
• 123-78-4
• 4-Sphingenine
• D-Sphingosine
• Sphing-4-enine
• Sphingenine
• 4-trans-Sphingenine
• (4E)-Sphingenine
• (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol
• trans-D-erythro-2-Amino-4-octadecene-1,3-diol
• D-erythro-Sphingosine (synthetic)
• trans-4-Sphingenine
• dl-Erythro-sphingosine
• Erythro-dl-sphingosine
• Sphingoid
• (E,2S,3R)-2-aminooctadec-4-ene-1,3-diol
• c18-erythro-sphingenine
• (2S,3R)-Sphingosine
• (2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
• 4-octadecene-1,3-diol, 2-amino-, (2S,3R,4E)-
• C18-Sphingosine
• D-erythro-C18-Sphingosine
• (-)-D-erythro-Sphingosine
• (-)-Sphingosine
• (E)-2-Amino-4-octadecan-1,3-diol
• CCRIS 6899
• erythro-4-Sphingenine
• 2-Aminooctadec-4-ene-1,3-diol
• (2S,3R)-2-aminooctadec-4-ene-1,3-diol
• (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol
• 2S-Amino-4E-octadecene-1,3R-diol
• UNII-NGZ37HRE42
• NGZ37HRE42
• UNII-0Y6SVQ612Q
• 0Y6SVQ612Q
• 4-Octadecene-1,3-diol, 2-amino-, (R-(R*,S*-(E)))-
• CHEBI:16393
• EINECS 204-651-3
• 4-Octadecene-1,3-diol, 2-amino-, (E)-dl-erythro-
• 4-Octadecene-1,3-diol, 2-amino-, (R*,S*-(E))-
• 4-Octadecene-1,3-diol, 2-amino-, (2R,3S,4E)-rel-
• (E)-D-erythro-4-octadecene-1,3-diol
• (2S,3R)-2-Amino-4-octadecene-1,3-diol
• MLS-0412588.0001
• sphingosin
• 2733-29-1
• (4E)-sphing-4-enine
• 4-Octadecene-1,3-diol, 2-amino-, (R*,S*-(E))-(+)-
• SMR000857107
• erythro-C18-Sphingosine
• CHEMBL67166
• MFCD00036751
• 4-Octadecene-1,3-diol, 2-amino-, [R-[R*,S*-(E)]]-
• C18 sphingosine
• D-erythrosphingosine
• Sphingosine d18:1
• D-Erythro-spinghosine
• D-Sphingosine, synthetic
• Sphingosine, C18 chain
• BiomolKI_000034
• SPHINGOSINE [MI]
• BiomolKI2_000042
• bmse000850
• D0L0YG
• (2S,3R,E)-2-Amino-4-octadecene-1,3-diol
• Lopac0_001049
• SCHEMBL19398
• BSPBio_001526
• MLS001332469
• MLS001332470
• MLS002172450
• Erythrosphingosine; erythro-C18-Sphingosine; trans-4-Sphingenine
• BMK1-D10
• BML3-C09
• GTPL2452
• SCHEMBL1471985
• BDBM83205
• CHEBI:26743
• cid_5280335
• DTXSID90861763
• HMS1361M08
• HMS1791M08
• HMS1989M08
• HMS2232M04
• HMS3402M08
• HMS3650M05
• D-(+)-erytho-4-trans-Sphingenine
• DL-ERYTHRO-SPHINGOSINE [MI]
• EX-A1428
• EI-155
• HB0239
• LMSP01010001
• s2210
• D-Sphingosine, >=98.0% (TLC)
• AKOS024458590
• CCG-100638
• DB03203
• ERYTHRO-SPHINGOSINE, (+/-)-
• IDI1_033996
• NCGC00024697-02
• NCGC00024697-03
• NCGC00024697-04
• NCGC00024697-05
• NCGC00024697-06
• NCGC00024697-07
• AC-28329
• AS-66175
• HY-101047
• CS-0020759
• S0874
• (E,2S,3R)-2-amino-4-octadecene-1,3-diol
• (E,2S,3R)-2-azanyloctadec-4-ene-1,3-diol
• C00319
• F20671
• Q46298
• D-Sphingosine, from bovine brain, ~99% (TLC)
• A901185
• SR-01000597656
• (2S,3R)-(E)-2-amino-1,3-dihydroxy-4-octadecene
• (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-ene-1-ol
• J-004983
• Sphingosine (d18:1), D-erythro-sphingosine, powder
• SR-01000597656-1
• [R-[R*,S*-(E)]]-2-amino-4-Octadecene-1,3-diol
• E66DE871-3B37-406A-891B-A804BDC7ABF9
• 4-Octadecene-1,3-diol, 2-amino-, (2S,3R,4E)- (9CI)
• 4-OCTADECENE-1,3-DIOL, 2-AMINO-, (E)-D-ERYTHRO-
• 4-Octadecene-1,3-diol, 2-amino-, (E)-D-erythro- (8CI)
• 4-Octadecene-1,3-diol, 2-amino-, (R-(R*,S*-(E)))
• D-(+)-erythro-1,3-dihydroxy-2-amino-4-trans-octadecene
• 4-Octadecene-1,3-diol, 2-amino-, [R*,S*-(E)]-(.+.)-
• 4-OCTADECENE-1,3-DIOL, 2-AMINO-, (R*,S*-(E))-(+/-)-
• Brain Sphingosine, D-erythro-Sphingosine (Brain, Porcine), powder
• 89164-20-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2524	P06280	Alpha-galactosidase A	4466.8 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	44668.4 nM; 44668.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4423	P51684	C-C chemokine receptor type 6	20900 nM	IC50	via CMAUP
CHEMBL1075315	P32302	C-X-C chemokine receptor type 5	32494 nM	IC50	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	35481.3 nM	Potency	via CMAUP
CHEMBL1293278	O75496	Geminin	15848.9 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	22387.2 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	5011.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	3860 nM	IC50	PMID: 19467599
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	1560 nM	IC50	PMID: 19467599
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	631 nM; 631 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	0.9 nM	Potency	via Super-PRED
CHEMBL6089	P61088	Ubiquitin-conjugating enzyme E2 N	6425 nM; 6200 nM	IC50; IC50	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	98.06%	97.29%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.93%	92.86%
CHEMBL230	P35354	Cyclooxygenase-2	95.96%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.37%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.31%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.68%	92.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.55%	96.09%
CHEMBL2885	P07451	Carbonic anhydrase III	94.42%	87.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.79%	93.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.34%	100.00%
CHEMBL1907	P15144	Aminopeptidase N	87.31%	93.31%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.40%	96.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.39%	89.34%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	83.55%	91.81%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.48%	91.11%
CHEMBL2664	P23526	Adenosylhomocysteinase	83.26%	86.67%
CHEMBL299	P17252	Protein kinase C alpha	82.89%	98.03%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	82.85%	85.94%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.98%	96.00%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	81.12%	94.01%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.63%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.24%	90.17%
CHEMBL4581	P52732	Kinesin-like protein 1	80.22%	93.18%

Plants that contains it

• Glycine max
• Pogostemon cablin

Cross-Links

• PubChem: 5280335
• NPASS: NPC55068
• ChEMBL: CHEMBL67166
• LOTUS: LTS0151451
• wikiData: Q46298