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
CHEMBL225155
CAS Number
26993-30-6
TTD ID
D07UGA
VARIDT ID
DR00118
INTEDE ID
DR1811
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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]
CCN family member 2 (CCN2) OTC39NSU CCN2_HUMAN Gene/Protein Processing [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 [10]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [11]
Laminin subunit alpha-3 (LAMA3) OTFME7HT LAMA3_HUMAN Gene/Protein Processing [12]
Laminin subunit beta-3 (LAMB3) OTFPU6W8 LAMB3_HUMAN Gene/Protein Processing [12]
Laminin subunit gamma-2 (LAMC2) OTJMTM72 LAMC2_HUMAN Gene/Protein Processing [12]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [13]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [13]
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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
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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 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.
10 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.
11 Phospholipase D activation by sphingosine 1-phosphate regulates interleukin-8 secretion in human bronchial epithelial cells. J Biol Chem. 2002 Aug 16;277(33):30227-35. doi: 10.1074/jbc.M111078200. Epub 2002 May 30.
12 Increase of laminin 5 synthesis in human keratinocytes by acute wound fluid, inflammatory cytokines and growth factors, and lysophospholipids. Br J Dermatol. 2004 Nov;151(5):961-70. doi: 10.1111/j.1365-2133.2004.06175.x.
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.