Identification

Name
Sphingosine
Accession Number
DB03203  (EXPT02945)
Type
Small Molecule
Groups
Experimental
Description

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)

Structure
Thumb
Synonyms
Not Available
Categories
UNII
NGZ37HRE42
CAS number
123-78-4
Weight
Average: 299.4919
Monoisotopic: 299.282429433
Chemical Formula
C18H37NO2
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])[[email protected]@]([H])(O)[[email protected]@]([H])(N)CO

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlycolipid transfer proteinNot AvailableHuman
UGenome polyproteinNot AvailablePoliovirus type 1 (strain Mahoney)
UGenome polyproteinNot AvailableHRV-14
UGenome polyproteinNot AvailableSVDV
UGenome polyproteinNot AvailablePoliovirus type 3 (strains P3/Leon/37 and P3/Leon 12A[1]B)
UPoliovirus receptorNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
LumacaftorThe serum concentration of Sphingosine can be decreased when it is combined with Lumacaftor.Approved
RanolazineThe serum concentration of Sphingosine can be increased when it is combined with Ranolazine.Approved, Investigational
Food Interactions
Not Available

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
Therapeutic Targets Database
DNC001357
IUPHAR
2452
Guide to Pharmacology
GtP Drug Page
HET
SQS
PDB Entries
3vzb

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)67 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0039 mg/mLALOGPS
logP5.15ALOGPS
logP4.57ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.89 m3·mol-1ChemAxon
Polarizability39.37 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.5839
Caco-2 permeable-0.573
P-glycoprotein substrateSubstrate0.5295
P-glycoprotein inhibitor INon-inhibitor0.9155
P-glycoprotein inhibitor IINon-inhibitor0.7564
Renal organic cation transporterNon-inhibitor0.8759
CYP450 2C9 substrateNon-substrate0.8247
CYP450 2D6 substrateNon-substrate0.706
CYP450 3A4 substrateNon-substrate0.7191
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9151
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7332
Ames testNon AMES toxic0.7957
CarcinogenicityNon-carcinogens0.7754
BiodegradationReady biodegradable0.748
Rat acute toxicity1.6142 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8822
hERG inhibition (predictor II)Non-inhibitor0.854
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0udi-1690000000-901fd6e5629da37ac9f1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0590000000-9720cbb900a4b9086b5c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0690000000-9ed3190e406f4e0b00e8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0091000000-2b5eca8b8e37ffe56f2c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0gx0-3490000000-3e9102bddf33795a737a

Taxonomy

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
Secondary alcohol / 1,2-aminoalcohol / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Primary alcohol / Organooxygen compound / Primary aliphatic amine / Alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
sphing-4-enine (CHEBI:16393) / Sphing-4-enines (Sphingosines) (C00319) / Sphing-4-enines (Sphingosines) (LMSP01010001)

Targets

Kind
Protein
Organism
Human
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
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
  1. 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. [PubMed:10592235]
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
  1. 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. [PubMed:10592235]
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
  1. 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. [PubMed:10592235]
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
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10592235]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:15618625]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:24