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Showing Compound Phytosphingosine (FDB023381)

Record Information
Version1.0
Creation date2011-09-21 00:29:03 UTC
Update date2020-09-17 15:39:19 UTC
Primary IDFDB023381
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhytosphingosine
DescriptionPhytosphingosine, also known as SP(t18:0), belongs to the class of organic compounds known as 1,3-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 C3 atom. Thus, phytosphingosine is considered to be a sphingoid base lipid molecule. Phytosphingosine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Phytosphingosine exists in all eukaryotes, ranging from yeast to humans. Phytosphingosine is a sphingoid base, a fundamental building block of more complex sphingolipids.
CAS Number554-62-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-D-HydroxysphinganineChEBI
4-R-HydroxyoctadecasphinganineChEBI
(+)-D-Ribo-phytosphingosineHMDB
4-D-Hydroxy-sphinganineHMDB
4D-HydroxysphinganineHMDB
C18-PhytosphingosineHMDB
D-Ribo-1,3,4-trihydroxy-2-aminooctadecaneHMDB
D-Ribo-2-amino-1,3,4-octadecanetriolHMDB
[2S-(2R*,3R*,4S*)]-2-amino-1,3,4-octadecanetriolHMDB
8-(Z-e)-C18-PhytosphingenineHMDB
(2S,3S,4R)-2-Amino-1,3,4-octadecanetriolHMDB
(2S,3S,4R)-2-Amino-1,3,4-trihydroxyoctadecaneHMDB
D-Ribo-phytosphingosineHMDB
SP(t18:0)HMDB
PhytosphingosineHMDB
(+)-D-ribo-Phytosphingosinehmdb
[2S-(2R*,3R*,4S*)]-2-amino-1,3,4-Octadecanetriolhmdb
4-D-hydroxy-Sphinganinehmdb
D-ribo-1,3,4-Trihydroxy-2-aminooctadecanehmdb
D-ribo-2-amino-1,3,4-Octadecanetriolhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP3.96ALOGPS
logP3.7ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)13.45ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity92.29 m³·mol⁻¹ChemAxon
Polarizability41.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H39NO3
IUPAC name(2S,3S,4R)-2-aminooctadecane-1,3,4-triol
InChI IdentifierInChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1
InChI KeyAERBNCYCJBRYDG-KSZLIROESA-N
Isomeric SMILESCCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO
Average Molecular Weight317.5072
Monoisotopic Molecular Weight317.292994119
Classification
Description Belongs to the class of organic compounds known as 1,3-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 C3 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,3-aminoalcohols
Alternative Parents
Substituents
  • 1,3-aminoalcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Polyol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPhytosphingosine, non-derivatized, GC-MS Spectrumsplash10-001i-1910000000-6a156f8b67eb8d2e2af8Spectrum
GC-MSPhytosphingosine, non-derivatized, GC-MS Spectrumsplash10-0udi-0590000000-55f1259ff17447451d03Spectrum
GC-MSPhytosphingosine, non-derivatized, GC-MS Spectrumsplash10-001i-1910000000-6a156f8b67eb8d2e2af8Spectrum
GC-MSPhytosphingosine, non-derivatized, GC-MS Spectrumsplash10-0udi-0590000000-55f1259ff17447451d03Spectrum
Predicted GC-MSPhytosphingosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08fu-9240000000-f0c822bc0197665bc676Spectrum
Predicted GC-MSPhytosphingosine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pxr-8498250000-59c3446ba7cde2700251Spectrum
Predicted GC-MSPhytosphingosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhytosphingosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-9025000000-41591a03203ebe6783ab2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-03yi-9055000000-c534f58f04d1f008079f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-014i-0009000000-2467642b22875f4e99a12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-014i-0009000000-94b30bf1ae7ab25e566e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-03xr-9037000000-2e7ea43f8d534e10f1d42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-03di-9020000000-ac9c04a9082abb540f222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-03di-9010000000-e1fe657c8693bf3f19e72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 26V, positivesplash10-03di-9000000000-f71f3038d0b8478d679c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-03di-9000000000-795a4947f722e8f616202020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 38V, positivesplash10-03di-9000000000-e62d8c5bcb55aa1666032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 44V, positivesplash10-03di-9000000000-cb05f289ecdcd16de4e72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 52V, positivesplash10-03di-9000000000-e898ac84341e318b58622020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 60V, positivesplash10-08fr-9000000000-b048fe168eacee2593942020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 72V, positivesplash10-0900-9000000000-d72ddb3ba2da45266fab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, positivesplash10-0udi-0039000000-33d42068332d814a2c832020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, positivesplash10-06yt-6940000000-fdeb46044349d9fcc9962020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, positivesplash10-0006-9000000000-981a59d4f1dd5e03c5ac2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, positivesplash10-0ik9-0190000000-d31bcfd06b73972a43002020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, positivesplash10-03di-2290000000-b7855c3c2203ca25bab32020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1029000000-ea43e68bb4fffc9657b12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9121000000-cce64d1dcf28012d72f82016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9520000000-d95a37794c98d95dd2b02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2097000000-1f5b8c8eefe1a491d0c92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-9060000000-7550c32b4e1dfcbc45932016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9020000000-5cbe1fbb421cacd42e982016-09-12View Spectrum
NMRNot Available
ChemSpider ID108921
ChEMBL IDCHEMBL236036
KEGG Compound IDC12144
Pubchem Compound ID122121
Pubchem Substance IDNot Available
ChEBI ID46961
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04610
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Acid ceramidaseASAH1Q13510
Alkaline ceramidase 2ACER2Q5QJU3
Alkaline ceramidase 1ACER1Q8TDN7
Ganglioside GM2 activatorGM2AP17900
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit PPIGPP57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
T-cell surface glycoprotein CD1e, membrane-associatedCD1EP15812
Epididymal secretory protein E1NPC2P61916
Antigen-presenting glycoprotein CD1dCD1DP15813
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseB3GNT5Q9BYG0
Beta-1,3-galactosyltransferase 5B3GALT5Q9Y2C3
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Non-lysosomal glucosylceramidaseGBA2Q9HCG7
GPI-anchor transamidasePIGKQ92643
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
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References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference