Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1811)
Drug Name
YP-005
Synonyms
D-erythro-Sphingosine-1-phosphate; D-erythro-sphingosine 1-phosphate; DUYSYHSSBDVJSM-KRWOKUGFSA-N; Sphing-4-enine 1-phosphate; Sphing-4-enine-1-phosphate; Sphingosine 1-phosphate; Sphingosine 1-phosphic acid; YVE187NJ1U; sphingosine-1-phosphate; (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl dihydrogen phosphate; 26993-30-6; 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (2S,3R,4E)-; C18-Sphingosine 1-phosphate; CHEBI:37550; CHEMBL225155; S1P; UNII-YVE187NJ1U
Indication Acne vulgaris [ICD11: ED80] Phase 1 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 379.5 Topological Polar Surface Area 113
Heavy Atom Count 25 Rotatable Bond Count 17
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5283560
PubChem SID
8381 ; 841938 ; 3153153 ; 4266347 ; 11039024 ; 11538026 ; 14853517 ; 14902393 ; 24893757 ; 24899853 ; 26754964 ; 26754965 ; 26759550 ; 29214822 ; 39316963 ; 47736194 ; 50069271 ; 53790239 ; 56310719 ; 56314086 ; 56314115 ; 57358934 ; 79196702 ; 85230694 ; 91616005 ; 99431555 ; 103513044 ; 104045126 ; 104046551 ; 112629138 ; 113860431 ; 123055038 ; 135061792 ; 135651563 ; 137123351 ; 141225271 ; 144107094 ; 162223883 ; 163687305 ; 164808502 ; 175443701 ; 179205494 ; 226395983 ; 228659508 ; 241182370 ; 241375387 ; 250135272 ; 252467313
ChEBI ID
CHEBI:37550
CAS Number
26993-30-6
TTD Drug ID
D07UGA
Formula
C18H38NO5P
Canonical SMILES
CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Hexadecenal DM003597
5280541
Unclear 1 [5]
Phosphoethanolamine DM003594
1015
Unclear 1 [5]
Sphingosine DM003599
5280335
Unclear 1 [2]
CDP-ethanolamine DM003595
123727
Unclear 2 [6]
Ceramide DM020006 N. A. Unclear 2 [6]
Hexadecanal DM003541
984
Unclear 2 [6]
Palmitate DM003598
985
Unclear 3 [6]
Phosphatidylethanolamine DM003596
5327011
Unclear 3 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013166 YP-005 Phosphoethanolamine Unclear SGPL1 [5]
MR013169 YP-005 Hexadecenal Unclear SGPL1 [5]
MR013172 YP-005 Sphingosine Unclear ASAH2 [2]
MR013170 Hexadecenal Hexadecanal Unclear Unclear [6]
MR013167 Phosphoethanolamine CDP-ethanolamine Unclear Unclear [6]
MR013173 Sphingosine Ceramide Unclear Unclear [6]
MR013168 CDP-ethanolamine Phosphatidylethanolamine Unclear Unclear [6]
MR013171 Hexadecanal Palmitate Unclear Unclear [6]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Neutral ceramidase (ASAH2) DMEN143 Homo sapiens
ASAH2_HUMAN
3.5.1.-
[2]
Phospholipid phosphatase 1 (PLPP1) DME0444 Homo sapiens
PLPP1_HUMAN
3.1.3.4
[3]
Sphingosine kinase 1 (SPHK1) DME0484 Homo sapiens
SPHK1_HUMAN
2.7.1.91
[4]
Sphingosine kinase 2 (SPHK2) DME0483 Homo sapiens
SPHK2_HUMAN
2.7.1.91
[4]
Sphingosine-1-phosphate lyase 1 (SGPL1) DMEN142 Homo sapiens
SGPL1_HUMAN
4.1.2.27
[5]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Sphingosine kinase 1 (SPHK1) DME0484 Km = 0.014 microM
SPHK1_HUMAN
[4]
Sphingosine kinase 2 (SPHK2) DME0483 Km = 0.014 microM
SPHK2_HUMAN
[4]
References
1 ClinicalTrials.gov (NCT01466322) A Study to Assess the Relative Bioavailability of Different Formulations of GSK2018682, a Sphingosine-1-phosphate Receptor Subtype 1 Agonist, in Healthy Volunteers..
2 Sphingosine-1-Phosphate Metabolism in the Regulation of Obesity/Type 2 Diabetes
3 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.
4 Phosphorylation of the immunomodulatory drug FTY720 by sphingosine kinases. J Biol Chem. 2003 Nov 28;278(48):47408-15.
5 Sphingosine-1-phosphate metabolism: A structural perspective
6 Ceramide/sphingosine/sphingosine 1-phosphate metabolism on the cell surface and in the extracellular space

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