CHEBI:16393 - sphingosine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name sphingosine
ChEBI ID CHEBI:16393
Definition A sphing-4-enine in which the double bond is trans.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9224, CHEBI:15102, CHEBI:26741, CHEBI:207585
Supplier Information ChemicalBook:CB6134417, eMolecules:532057, eMolecules:28206777, ZINC000000025672
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Formula C18H37NO2
Net Charge 0
Average Mass 299.49190
Monoisotopic Mass 299.28243
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
InChIKey WWUZIQQURGPMPG-KRWOKUGFSA-N
SMILES CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sphingosine (CHEBI:16393) has role human metabolite (CHEBI:77746)
sphingosine (CHEBI:16393) has role mouse metabolite (CHEBI:75771)
sphingosine (CHEBI:16393) is a sphing-4-enine (CHEBI:26743)
sphingosine (CHEBI:16393) is conjugate base of sphingosine(1+) (CHEBI:57756)
sphingosine (CHEBI:16393) is enantiomer of L-erythro-sphingosine (CHEBI:46967)
Incoming α-psychosine (CHEBI:140280) has functional parent sphingosine (CHEBI:16393)
β-D-Gal-(1→3)-β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→3)]-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Sph (CHEBI:61814) has functional parent sphingosine (CHEBI:16393)
1-O-acyl-N-acylsphingosine (CHEBI:76222) has functional parent sphingosine (CHEBI:16393)
2-(2-hydroxyacyl)sphingosine (CHEBI:16456) has functional parent sphingosine (CHEBI:16393)
3-dehydrosphingosine (CHEBI:20096) has functional parent sphingosine (CHEBI:16393)
6-hydroxysphing-4E-enine (CHEBI:73900) has functional parent sphingosine (CHEBI:16393)
N,N-dimethylsphingosine (CHEBI:78759) has functional parent sphingosine (CHEBI:16393)
N-acyl-β-D-galactosylsphingosine (CHEBI:18390) has functional parent sphingosine (CHEBI:16393)
N-acylsphingosine (CHEBI:52639) has functional parent sphingosine (CHEBI:16393)
N-decanoylsphingosine 1-phosphate (CHEBI:73147) has functional parent sphingosine (CHEBI:16393)
N-docosanoylsphingosine-1-phosphate (CHEBI:73138) has functional parent sphingosine (CHEBI:16393)
N-dodecanoylsphingosine 1-phosphate (CHEBI:72718) has functional parent sphingosine (CHEBI:16393)
N-hexacosanoylsphingosine 1-phosphate (CHEBI:73135) has functional parent sphingosine (CHEBI:16393)
N-hexadecanoylsphingosine 1-phosphate (CHEBI:73145) has functional parent sphingosine (CHEBI:16393)
N-icosanoylsphingosine 1-phosphate (CHEBI:73140) has functional parent sphingosine (CHEBI:16393)
N-octadecanoylsphingosine 1-phosphate (CHEBI:73144) has functional parent sphingosine (CHEBI:16393)
N-tetracosanoylsphingosine 1-phosphate (CHEBI:73137) has functional parent sphingosine (CHEBI:16393)
N-tetradecanoylsphingosine 1-phosphate (CHEBI:73146) has functional parent sphingosine (CHEBI:16393)
D-glucosylsphingosine (CHEBI:4177) has functional parent sphingosine (CHEBI:16393)
hexosyl-(1↔1ʼ)-N-acylsphingosine (CHEBI:82917) has functional parent sphingosine (CHEBI:16393)
psychosine (CHEBI:16874) has functional parent sphingosine (CHEBI:16393)
sphinga-4E,14Z-dienine (CHEBI:73889) has functional parent sphingosine (CHEBI:16393)
sphinga-4E,8E-dienine (CHEBI:72800) has functional parent sphingosine (CHEBI:16393)
sphingosine 1-phosphate (CHEBI:37550) has functional parent sphingosine (CHEBI:16393)
sphingosine-1-phosphocholine (CHEBI:17689) has functional parent sphingosine (CHEBI:16393)
sphingosine-based sphingolipid (CHEBI:82830) has functional parent sphingosine (CHEBI:16393)
sphingosylphosphocholine acid (CHEBI:52897) has functional parent sphingosine (CHEBI:16393)
sphingosine(1+) (CHEBI:57756) is conjugate acid of sphingosine (CHEBI:16393)
L-erythro-sphingosine (CHEBI:46967) is enantiomer of sphingosine (CHEBI:16393)
IUPAC Name
(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol
Synonyms Sources
(2S,3R)-(E)-2-amino-1,3-dihydroxy-4-octadecene ChEBI
(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-ene-1-ol ChEBI
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol CBN
(2S,3R,E)-2-aminooctadec-4-ene-1,3-diol ChEMBL
(4E)-sphing-4-enine IUPAC
(4E)-sphingenine CBN
(E)-2-amino-4-octadecan-1,3-diol ChemIDplus
(E)-D-erythro-4-octadecene-1,3-diol ChEBI
2-amino-4-octadecene-1,3-diol ChEBI
C18 sphingosine ChEBI
D-(+)-erythro-1,3-dihydroxy-2-amino-4-trans-octadecene ChEBI
D-erythro-sphingosine ChEBI
Sph CBN
Sphing-4-enine KEGG COMPOUND
Sphingenine KEGG COMPOUND
Sphingoid KEGG COMPOUND
sphingosin ChEBI
Sphingosine KEGG COMPOUND
Sphingosine d18:1 ChEBI
trans-4-sphingenine CBN
trans-D-erythro-2-amino-4-octadecene-1,3-diol ChEBI
Manual Xrefs Databases
C00319 KEGG COMPOUND
DB03203 DrugBank
HMDB0000252 HMDB
LMSP01010001 LIPID MAPS
SQS PDBeChem
View more database links
Registry Numbers Types Sources
123-78-4 CAS Registry Number ChemIDplus
1727294 Reaxys Registry Number Reaxys
4676153 Beilstein Registry Number Beilstein
Citations Types Sources
10453988 PubMed citation Europe PMC
16341241 PubMed citation Europe PMC
24731183 PubMed citation Europe PMC
8482346 PubMed citation Europe PMC
Last Modified
26 February 2018