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sphingosine 1-phosphate(1-)

AlkaPlorer ID: AK018807

Synonym: '26993-30-6', '(2S,3R,4E)-2-amino-4-octadecene-1,3-diol 1-(dihydrogen phosphate)', 'Sphing-4-enine 1-phosphate', 'D-erythro-sphingosine 1-phosphate', '(2S,3R,4E)-2-ammonio-3-hydroxyoctadec-4-en-1-yl phosphate', 'C18-Sphingosine 1-phosphate', 'sphingosine 1-phosphate anion', 'Sphingosine 1-phosphate', 'S1P', '(2-amino-3-hydroxy-octadec-4-enoxy)phosphonic acid', 'sphing-4-enine 1-phosphate', 'Sphingosine 1-phosphic acid', 'sphingosine-1-phosphate', 'sphingosine 1-phosphate'

IUPAC Name: [(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate

Structure

SMILES: CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O

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InChI: InChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1

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InChIKey: DUYSYHSSBDVJSM-KRWOKUGFSA-N

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Reference

PubChem CID: 10883396

CAS: 26993-30-6

LOTUS: LTS0010692

NPASS: NPC324638

Properties Information

Molecule Weight: 379.47800000000007

TPSA？: 113.01000000000002

MolLogP？: 4.041200000000004

Number of H-Donors: 4

Number of H-Acceptors: 4

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Adhesion G-protein coupled receptor F1 %Inhib (Mean) -5.29 % 10.6019/CHEMBL5209801
Homo sapiens Adhesion G-protein coupled receptor F1 %Max (Mean) 12.85 % 10.6019/CHEMBL5209801
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 44668.4 nM None
Homo sapiens Alpha-2a adrenergic receptor %Inhib (Mean) -27.92 % 10.6019/CHEMBL5209801
Homo sapiens Alpha-2a adrenergic receptor %Max (Mean) 0.68 % 10.6019/CHEMBL5209801
Homo sapiens Apelin receptor %Inhib (Mean) 6.13 % 10.6019/CHEMBL5209801
Homo sapiens Apelin receptor %Max (Mean) -2.811 % 10.6019/CHEMBL5209801
Homo sapiens Beta-2 adrenergic receptor %Inhib (Mean) -35.98 % 10.6019/CHEMBL5209801
Homo sapiens Beta-2 adrenergic receptor %Max (Mean) -1.184 % 10.6019/CHEMBL5209801
Homo sapiens Bromodomain-containing protein 4 Delta TM -0.94 C None
Homo sapiens C5a anaphylatoxin chemotactic receptor %Inhib (Mean) -43.71 % 10.6019/CHEMBL5209801
Homo sapiens C5a anaphylatoxin chemotactic receptor %Max (Mean) -2.296 % 10.6019/CHEMBL5209801
Homo sapiens Casein kinase I delta Delta TM 0.07 C None
Homo sapiens C-X3-C chemokine receptor 1 %Inhib (Mean) -25.44 % 10.6019/CHEMBL5209801
Homo sapiens C-X3-C chemokine receptor 1 %Max (Mean) -2.24 % 10.6019/CHEMBL5209801
Homo sapiens Cyclin-dependent kinase 2 Delta TM 0.77 C None
Homo sapiens Fibroblast Growth Rate -0.68 None 10.6019/CHEMBL5058564
Homo sapiens Fibroblast Growth Rate -0.13 None 10.6019/CHEMBL5058564
Homo sapiens Fibroblast Growth Rate 0.17 None 10.6019/CHEMBL5058564
Homo sapiens Fibroblast Growth Rate 0.19 None 10.6019/CHEMBL5058564
Homo sapiens Fibroblast Growth Rate 0.53 None 10.6019/CHEMBL5058564
Homo sapiens Fibroblast Growth Rate 0.63 None 10.6019/CHEMBL5058564
Homo sapiens Fibroblast Growth Rate 0.82 None 10.6019/CHEMBL5058564
Homo sapiens Fibroblast growth factor receptor 3 Delta TM 0.28 C None
Homo sapiens Glucagon-like peptide 1 receptor %Inhib (Mean) -18.51 % 10.6019/CHEMBL5209801
Homo sapiens Glucagon-like peptide 1 receptor %Max (Mean) -2.829 % 10.6019/CHEMBL5209801
Homo sapiens Glucose-dependent insulinotropic receptor %Inhib (Mean) -5.61 % 10.6019/CHEMBL5209801
Homo sapiens Glucose-dependent insulinotropic receptor %Max (Mean) -1.212 % 10.6019/CHEMBL5209801
Homo sapiens Glycogen synthase kinase-3 beta Delta TM -0.18 C None
Homo sapiens G-protein coupled receptor 120 %Inhib (Mean) -14.8 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 120 %Max (Mean) -0.5299 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 35 %Inhib (Mean) -30.35 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 35 %Max (Mean) 1.964 % 10.6019/CHEMBL5209801
Homo sapiens HEK-293T Growth Rate -0.22 None 10.6019/CHEMBL5058564
Homo sapiens HEK-293T Growth Rate -0.17 None 10.6019/CHEMBL5058564
Homo sapiens HEK-293T Growth Rate 0.04 None 10.6019/CHEMBL5058564
Homo sapiens HEK-293T Growth Rate 0.22 None 10.6019/CHEMBL5058564
Homo sapiens HEK-293T Growth Rate 0.27 None 10.6019/CHEMBL5058564
Homo sapiens HEK-293T Growth Rate 0.48 None 10.6019/CHEMBL5058564
Homo sapiens HEK-293T Growth Rate 0.52 None 10.6019/CHEMBL5058564
Homo sapiens Lipoxin A4 receptor %Inhib (Mean) -21.02 % 10.6019/CHEMBL5209801
Homo sapiens Lipoxin A4 receptor %Max (Mean) -2.681 % 10.6019/CHEMBL5209801
Homo sapiens MAP kinase ERK2 Delta TM 0.22 C None
Homo sapiens Peregrin Delta TM -0.67 C None
Homo sapiens Serine/threonine-protein kinase Aurora-A Delta TM -0.03 C None
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Activity 60.0 % 10.1021/acs.jmedchem.6b00089
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Activity 90.0 % 10.1021/acs.jmedchem.6b00089
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Activity 100.0 % 10.1021/acs.jmedchem.6b00089
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Activity nan None 10.1016/j.bmc.2014.06.038
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Activity nan None 10.1016/j.bmcl.2015.10.026
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Activity nan None 10.1021/jm502021d
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Activity nan None 10.1038/nchembio.173
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 0.027 nM 10.1016/j.bmcl.2010.02.006
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 0.062 nM 10.1021/ml500389m
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 0.1 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 0.55 nM 10.1016/j.bmcl.2006.10.014
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 0.9 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 2.8 nM 10.1016/j.bmcl.2015.11.090
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 4.25 nM 10.1021/ml400194r
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 4.5 nM 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 4.5 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 5.6 nM 10.1016/j.bmcl.2010.02.098
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 5.6 nM 10.1016/j.bmcl.2012.11.053
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 7.9 nM 10.1016/j.bmcl.2008.11.072
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 18.0 nM 10.1016/j.bmcl.2011.10.085
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 20.0 nM 10.1016/j.bmcl.2004.07.030
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 EC50 25.3 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Efficacy 91.0 % 10.1016/j.bmcl.2011.10.085
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Emax 1.0 None 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 IC50 0.16 nM 10.1016/j.bmcl.2004.02.106
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 IC50 0.47 nM 10.1016/j.bmcl.2008.11.072
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 IC50 0.67 nM 10.1021/jm0492507
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 IC50 0.78 nM 10.1016/j.bmcl.2010.02.098
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 IC50 1.4 nM 10.1016/j.bmcl.2017.12.010
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 IC50 1.4 nM 10.1039/d1md00357g
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 Inhibition nan % 10.1038/nchembio.173
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 %Inhib (Mean) -56.85 % 10.6019/CHEMBL5209801
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 %Max (Mean) 43.49 % 10.6019/CHEMBL5209801
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 Activity nan None 10.1021/jm502021d
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 0.2 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 0.449 nM 10.1016/j.bmcl.2010.02.006
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 0.7 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 1.1 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 1.2 nM 10.1016/j.bmcl.2004.07.030
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 1.6 nM 10.1016/j.bmcl.2006.10.014
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 2.4 nM 10.1016/j.bmcl.2010.02.098
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 2.4 nM 10.1016/j.bmcl.2012.11.053
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 3.0 nM 10.1016/j.bmcl.2008.11.072
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 3.94 nM 10.1021/ml400194r
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 8.7 nM 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 8.7 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 EC50 79.0 nM 10.1016/j.bmcl.2015.11.090
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 Emax 1.0 None 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 IC50 0.04 nM 10.1016/j.bmcl.2004.02.106
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 IC50 0.26 nM 10.1021/jm0492507
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 IC50 0.4 nM 10.1016/j.bmcl.2017.12.010
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 IC50 0.4 nM 10.1039/d1md00357g
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 IC50 0.66 nM 10.1016/j.bmcl.2008.11.072
Homo sapiens Sphingosine 1-phosphate receptor Edg-3 IC50 0.92 nM 10.1016/j.bmcl.2010.02.098
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 EC50 0.7 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 EC50 1.3 nM 10.1021/ml400194r
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 EC50 2.2 nM 10.1016/j.bmcl.2004.07.030
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 EC50 2.9 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 EC50 8.3 nM 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 EC50 8.3 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 EC50 43.9 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 Emax 1.0 None 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 IC50 0.23 nM 10.1016/j.bmcl.2004.02.106
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 IC50 0.35 nM 10.1021/jm0492507
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 IC50 3.6 nM 10.1016/j.bmcl.2017.12.010
Homo sapiens Sphingosine 1-phosphate receptor Edg-5 IC50 3.6 nM 10.1039/d1md00357g
Homo sapiens Sphingosine 1-phosphate receptor Edg-5/Sphingosine 1-phosphate receptor Edg-3 Activity nan None 10.1016/j.bmcl.2014.08.045
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 EC50 7.9 nM 10.1016/j.bmcl.2006.10.014
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 EC50 13.0 nM 10.1021/ml400194r
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 EC50 37.0 nM 10.1016/j.bmcl.2004.07.030
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 EC50 164.0 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 EC50 270.0 nM 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 EC50 270.0 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 EC50 nan nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 Emax 1.0 None 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 IC50 1.04 nM 10.1016/j.bmcl.2010.02.098
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 IC50 2.4 nM 10.1016/j.bmcl.2008.11.072
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 IC50 2.9 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 IC50 23.0 nM 10.1016/j.bmcl.2004.02.106
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 IC50 34.0 nM 10.1021/jm0492507
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 IC50 151.0 nM 10.1016/j.bmcl.2017.12.010
Homo sapiens Sphingosine 1-phosphate receptor Edg-6 IC50 151.0 nM 10.1039/d1md00357g
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 EC50 0.2 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 EC50 0.91 nM 10.1016/j.bmcl.2006.10.014
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 EC50 1.7 nM 10.1016/j.bmcl.2004.07.030
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 EC50 1.8 nM 10.1021/ml400194r
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 EC50 9.2 nM 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 EC50 9.2 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 EC50 43.9 nM 10.1016/s0960-894x(03)00812-6
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 EC50 121.0 nM 10.1021/jm100181s
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 Emax 1.0 None 10.1016/j.bmcl.2005.05.097
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 IC50 0.55 nM 10.1021/jm0492507
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 IC50 1.1 nM 10.1016/j.bmcl.2008.11.072
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 IC50 2.0 nM 10.1016/j.bmcl.2010.02.098
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 IC50 3.1 nM 10.1016/j.bmcl.2017.12.010
Homo sapiens Sphingosine 1-phosphate receptor Edg-8 IC50 3.1 nM 10.1039/d1md00357g
Homo sapiens Transcription intermediary factor 1-alpha Delta TM -0.59 C None
Homo sapiens Type-1 angiotensin II receptor %Inhib (Mean) -23.16 % 10.6019/CHEMBL5209801
Homo sapiens Type-1 angiotensin II receptor %Max (Mean) 1.42 % 10.6019/CHEMBL5209801
Homo sapiens Tyrosine-protein kinase ABL Delta TM 0.54 C None
Homo sapiens U2OS Growth Rate 0.31 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.88 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.89 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.95 None 10.6019/CHEMBL5058564
Homo sapiens U2OS Growth Rate 0.99 None 10.6019/CHEMBL5058564
None NON-PROTEIN TARGET Migration 6.0 % 10.1016/S0960-894X(00)80600-9
None NON-PROTEIN TARGET Migration 8.0 % 10.1016/S0960-894X(00)80600-9
None NON-PROTEIN TARGET Migration 10.0 % 10.1016/S0960-894X(00)80600-9
None NON-PROTEIN TARGET Migration 12.0 % 10.1016/S0960-894X(00)80600-9
None NON-PROTEIN TARGET Migration 17.0 % 10.1016/S0960-894X(00)80600-9
None NON-PROTEIN TARGET Migration 34.0 % 10.1016/S0960-894X(00)80600-9
None NON-PROTEIN TARGET Migration 41.0 % 10.1016/S0960-894X(00)80600-9
None NON-PROTEIN TARGET Migration 82.0 % 10.1016/S0960-894X(00)80600-9
None NON-PROTEIN TARGET Migration 122.0 % 10.1016/S0960-894X(00)80600-9
None Unchecked EC50 2.1 nM 10.1021/ml500389m
None Unchecked EC50 2.1 nM 10.1021/ml500422m
None Unchecked EC50 4.5 nM 10.1016/j.bmcl.2005.07.057
None Unchecked EC50 8.3 nM 10.1016/j.bmcl.2005.07.057
None Unchecked EC50 8.7 nM 10.1016/j.bmcl.2005.07.057
None Unchecked EC50 9.2 nM 10.1016/j.bmcl.2005.07.057
None Unchecked EC50 270.0 nM 10.1016/j.bmcl.2005.07.057
None Unchecked Potency 14125.4 nM None
None Unchecked Ratio EC50 0.4 None 10.1016/j.bmcl.2008.11.072
None Unchecked Ratio EC50 0.9 None 10.1021/ml400194r

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT008674 CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO>>CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O RXN3DJ-11417
AKRT008676 CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O>>CCCCCCCCCCCCC/C=C/C=O RXN3DJ-11230
AKRT008677 CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O>>CCCCCCCCCCCCC/C=C/C=O.NCCOP(=O)(O)O None
AKRT008678 CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O>>CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO RXN3DJ-25
AKRT008679 CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O>>CCCCCCCCCCCCCCCC=O MNXR134666
AKRT008680 CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O>>NCCOP(=O)(O)O RXN3DJ-11230
AKRT008682 CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)OCC[N+](C)(C)C>>CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O 38919
AKRT008922 CCCCCCCCCCCCCCCC(=O)O.NCCOP(=O)(O)O>>CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(=O)(O)O MNXR104366