Details of the Drug

General Information of Drug (ID: DMJCQKA)

Drug Name
Sphingosine-1-phosphate
Synonyms
Sphingosine 1-phosphate; sphingosine-1-phosphate; 26993-30-6; D-erythro-Sphingosine-1-phosphate; C18-Sphingosine 1-phosphate; Sphing-4-enine 1-phosphate; S1P; CHEBI:37550; D-erythro-sphingosine 1-phosphate; UNII-YVE187NJ1U; Sphingosine 1-phosphic acid; (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl dihydrogen phosphate; Sphing-4-enine-1-phosphate; YVE187NJ1U; CHEMBL225155; DUYSYHSSBDVJSM-KRWOKUGFSA-N; 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (2S,3R,4E)-; (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(Dihydroge
Indication
Disease Entry ICD 11 Status REF
Acne vulgaris ED80 Phase 1 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 379.5
Logarithm of the Partition Coefficient (xlogp) 1.9
Rotatable Bond Count (rotbonds) 17
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C18H38NO5P
IUPAC Name
[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate
Canonical SMILES
CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O
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
InChIKey
DUYSYHSSBDVJSM-KRWOKUGFSA-N
Cross-matching ID
PubChem CID
5283560
ChEBI ID
CHEBI:37550
CAS Number
26993-30-6
TTD ID
D07UGA
VARIDT ID
DR00118
INTEDE ID
DR1811

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sphingosine-1-phosphate receptor 1 (S1PR1) TT9JZCK S1PR1_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Protein spinster homolog 2 (SLC63A2) DT3Q1UO SPNS2_HUMAN Substrate [3]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [4]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Sphingosine kinase 1 (SPHK1) DELSNWC SPHK1_HUMAN Substrate [6]
Phospholipid phosphatase 1 (PLPP1) DE6WXTH PLPP1_HUMAN Substrate [7]
Sphingosine kinase 2 (SPHK2) DES1RUQ SPHK2_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4 (PLCB4) OTPA0QHW PLCB4_HUMAN Gene/Protein Processing [8]
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [9]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [10]
C-X-C chemokine receptor type 1 (CXCR1) OT5512B2 CXCR1_HUMAN Gene/Protein Processing [11]
CCN family member 2 (CCN2) OTC39NSU CCN2_HUMAN Gene/Protein Processing [12]
Cyclic AMP-responsive element-binding protein 1 (CREB1) OT1MDLA1 CREB1_HUMAN Post-Translational Modifications [13]
Epidermal growth factor receptor (EGFR) OTAPLO1S EGFR_HUMAN Post-Translational Modifications [9]
Guanine nucleotide-binding protein G(q) subunit alpha (GNAQ) OTOODWTU GNAQ_HUMAN Gene/Protein Processing [8]
Heat shock factor protein 1 (HSF1) OTYNJ4KP HSF1_HUMAN Gene/Protein Processing [14]
Hepatocyte growth factor (HGF) OTGHUA23 HGF_HUMAN Gene/Protein Processing [15]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Acne vulgaris
ICD Disease Classification ED80
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
P-glycoprotein 1 (ABCB1) DTP P-GP 7.23E-01 -8.20E-02 -3.22E-01
Breast cancer resistance protein (ABCG2) DTP BCRP 9.93E-01 -1.09E-01 -5.77E-01
Protein spinster homolog 2 (SLC63A2) DTP SPNS2 7.71E-01 1.32E-01 3.22E-01
Sphingosine kinase 2 (SPHK2) DME SPHK2 3.76E-01 -1.13E-01 -3.06E-01
Sphingosine kinase 1 (SPHK1) DME SPHK1 7.97E-01 -1.10E-01 -2.17E-01
Phospholipid phosphatase 1 (PLPP1) DME PLPP1 2.26E-01 -9.22E-02 -2.63E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 911).
2 Exploration of amino alcohol derivatives as novel, potent, and highly selective sphingosine-1-phosphate receptor subtype-1 agonists. Bioorg Med Chem Lett. 2010 Apr 15;20(8):2520-4.
3 The ABCs of membrane transporters in health and disease (SLC series): Introduction. Molecular Aspects of Medicine, 2013, 34(2-3):95-107. (GeneName=SLC63A2)
4 Estradiol induces export of sphingosine 1-phosphate from breast cancer cells via ABCC1 and ABCG2. J Biol Chem. 2010 Apr 2;285(14):10477-86.
5 Lipid dependence of ABC transporter localization and function. Chem Phys Lipids. 2009 Oct;161(2):57-64.
6 Phosphorylation of the immunomodulatory drug FTY720 by sphingosine kinases. J Biol Chem. 2003 Nov 28;278(48):47408-15.
7 Lipid phosphate phosphatase 3 regulates adipocyte sphingolipid synthesis, but not developmental adipogenesis or diet-induced obesity in mice. PLoS One. 2018 Jun 11;13(6):e0198063.
8 A natural piper-amide-like compound NED-135 exhibits a potent inhibitory effect on the invasive breast cancer cells. Chem Biol Interact. 2015 Jul 25;237:58-65. doi: 10.1016/j.cbi.2015.05.006. Epub 2015 May 14.
9 Taurocholate induces cyclooxygenase-2 expression via the sphingosine 1-phosphate receptor 2 in a human cholangiocarcinoma cell line. J Biol Chem. 2015 Dec 25;290(52):30988-1002.
10 Sphingosine kinase 1 and sphingosine-1-phosphate in oxidative stress evoked by 1-methyl-4-phenylpyridinium (MPP+) in human dopaminergic neuronal cells. Mol Neurobiol. 2014 Aug;50(1):38-48. doi: 10.1007/s12035-013-8622-4. Epub 2014 Jan 9.
11 Neutrophil sphingosine 1-phosphate and lysophosphatidic acid receptors in pneumonia. Am J Respir Cell Mol Biol. 2006 Feb;34(2):233-41. doi: 10.1165/rcmb.2005-0126OC. Epub 2005 Oct 13.
12 Actin polymerization-enhancing drugs promote ovarian follicle growth mediated by the Hippo signaling effector YAP. FASEB J. 2015 Jun;29(6):2423-30. doi: 10.1096/fj.14-267856. Epub 2015 Feb 17.
13 Prostacyclin induction by high-density lipoprotein (HDL) in vascular smooth muscle cells depends on sphingosine 1-phosphate receptors: effect of simvastatin. Thromb Haemost. 2008 Jul;100(1):119-26.
14 A Gene Expression Biomarker Predicts Heat Shock Factor 1 Activation in a Gene Expression Compendium. Chem Res Toxicol. 2021 Jul 19;34(7):1721-1737. doi: 10.1021/acs.chemrestox.0c00510. Epub 2021 Jun 25.
15 Arsenic requires sphingosine-1-phosphate type 1 receptors to induce angiogenic genes and endothelial cell remodeling. Am J Pathol. 2009 May;174(5):1949-58. doi: 10.2353/ajpath.2009.081016. Epub 2009 Apr 6.