Identification
- Generic Name
- Sphingosine
- DrugBank Accession Number
- DB03203
- Background
An amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. (Dorland, 28th ed)
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Sphingosine (DB03203)
- Weight
- Average: 299.4919
Monoisotopic: 299.282429433 - Chemical Formula
- C18H37NO2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGenome polyprotein Not Available Poliovirus type 1 (strain Mahoney) UGenome polyprotein Not Available HRV-14 UGenome polyprotein Not Available SVDV UGenome polyprotein Not Available Poliovirus type 3 (strains P3/Leon/37 and P3/Leon 12A[1]B) UPoliovirus receptor Not Available Humans UGlycolipid transfer protein Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- 1,2-aminoalcohols
- Alternative Parents
- Secondary alcohols / Primary alcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- 1,2-aminoalcohol / Alcohol / Aliphatic acyclic compound / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Primary aliphatic amine / Primary amine
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- sphing-4-enine (CHEBI:16393) / Sphing-4-enines (Sphingosines) (C00319) / Sphing-4-enines (Sphingosines) (LMSP01010001)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- NGZ37HRE42
- CAS number
- 123-78-4
- InChI Key
- WWUZIQQURGPMPG-KRWOKUGFSA-N
- 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
- IUPAC Name
- (2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
- SMILES
- [H]\C(CCCCCCCCCCCCC)=C(\[H])[C@@]([H])(O)[C@@]([H])(N)CO
References
- Synthesis Reference
Dennis Liotta, Alfred H. Merrill, "Method of preparing sphingosine derivatives." U.S. Patent US5110987, issued August, 1976.
US5110987- General References
- Not Available
- External Links
- KEGG Compound
- C00319
- PubChem Compound
- 5280335
- PubChem Substance
- 46505156
- ChemSpider
- 4444047
- BindingDB
- 83205
- ChEBI
- 16393
- ChEMBL
- CHEMBL67166
- ZINC
- ZINC000008195650
- Therapeutic Targets Database
- DNC001357
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- SQS
- Wikipedia
- Sphingosine
- PDB Entries
- 3vzb / 8c6d
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 1 Completed Treatment Pancreatic Cancer / Unspecified Adult Solid Tumor, Protocol Specific 1 Not Available Recruiting Not Available Alzheimer's Disease (AD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 67 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0039 mg/mL ALOGPS logP 5.15 ALOGPS logP 4.57 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 14.12 Chemaxon pKa (Strongest Basic) 9.23 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 66.48 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 91.89 m3·mol-1 Chemaxon Polarizability 39.37 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.995 Blood Brain Barrier + 0.5839 Caco-2 permeable - 0.573 P-glycoprotein substrate Substrate 0.5295 P-glycoprotein inhibitor I Non-inhibitor 0.9155 P-glycoprotein inhibitor II Non-inhibitor 0.7564 Renal organic cation transporter Non-inhibitor 0.8759 CYP450 2C9 substrate Non-substrate 0.8247 CYP450 2D6 substrate Non-substrate 0.706 CYP450 3A4 substrate Non-substrate 0.7191 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9151 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7332 Ames test Non AMES toxic 0.7957 Carcinogenicity Non-carcinogens 0.7754 Biodegradation Ready biodegradable 0.748 Rat acute toxicity 1.6142 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8822 hERG inhibition (predictor II) Non-inhibitor 0.854
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 209.9425712 predictedDarkChem Lite v0.1.0 [M-H]- 185.61954 predictedDeepCCS 1.0 (2019) [M+H]+ 209.9055712 predictedDarkChem Lite v0.1.0 [M+H]+ 188.53503 predictedDeepCCS 1.0 (2019) [M+Na]+ 208.9045712 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.28209 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Poliovirus type 1 (strain Mahoney)
- Pharmacological action
- Unknown
- General Function
- Structural molecule activity
- Specific Function
- Capsid protein VP1: Forms an icosahedral capsid of pseudo T=3 symmetry with capsid proteins VP2 and VP3. The capsid is 300 Angstroms in diameter, composed of 60 copies of each capsid protein and en...
- Gene Name
- Not Available
- Uniprot ID
- P03300
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 246538.14 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- HRV-14
- Pharmacological action
- Unknown
- General Function
- Structural molecule activity
- Specific Function
- Capsid protein VP1: Forms an icosahedral capsid of pseudo T=3 symmetry with capsid proteins VP2 and VP3. The capsid is 300 Angstroms in diameter, composed of 60 copies of each capsid protein and en...
- Gene Name
- Not Available
- Uniprot ID
- P03303
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 242989.38 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- SVDV
- Pharmacological action
- Unknown
- General Function
- Structural molecule activity
- Specific Function
- Capsid protein VP1: Forms an icosahedral capsid of pseudo T=3 symmetry with capsid proteins VP2 and VP3. The capsid is 300 Angstroms in diameter, composed of 60 copies of each capsid protein and en...
- Gene Name
- Not Available
- Uniprot ID
- P13900
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 243363.48 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Poliovirus type 3 (strains P3/Leon/37 and P3/Leon 12A[1]B)
- Pharmacological action
- Unknown
- General Function
- Structural molecule activity
- Specific Function
- Capsid protein VP1: Forms an icosahedral capsid of pseudo T=3 symmetry with capsid proteins VP2 and VP3. The capsid is 300 Angstroms in diameter, composed of 60 copies of each capsid protein and en...
- Gene Name
- Not Available
- Uniprot ID
- P03302
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 246162.675 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Virus receptor activity
- Specific Function
- Mediates NK cell adhesion and triggers NK cell effector functions. Binds two different NK cell receptors: CD96 and CD226. These interactions accumulates at the cell-cell contact site, leading to th...
- Gene Name
- PVR
- Uniprot ID
- P15151
- Uniprot Name
- Poliovirus receptor
- Molecular Weight
- 45302.3 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Lipid binding
- Specific Function
- Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be inv...
- Gene Name
- GLTP
- Uniprot ID
- Q9NZD2
- Uniprot Name
- Glycolipid transfer protein
- Molecular Weight
- 23849.6 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Sugawara T, Kinoshita M, Ohnishi M, Tsuzuki T, Miyazawa T, Nagata J, Hirata T, Saito M: Efflux of sphingoid bases by P-glycoprotein in human intestinal Caco-2 cells. Biosci Biotechnol Biochem. 2004 Dec;68(12):2541-6. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52