Bovine Metabolome Database: Showing metabocard for SM(d18:1/16:0) (BMDB0010169)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:01:13 UTC

Update Date

2020-06-04 20:40:48 UTC

BMDB ID

BMDB0010169

Secondary Accession Numbers

BMDB10169

Metabolite Identification

Common Name

SM(d18:1/16:0)

Description

(2-{[(2S,4E)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. Based on a literature review very few articles have been published on (2-{[(2S,4E)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Sphingomyelin	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-sphing-4-enine	MetBuilder
Sphingomyelin(D18:1/16:0)	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-sphingosine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-D-erythro-sphingosine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-4-sphingenine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-D-sphingosine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-sphingenine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-erythro-4-sphingenine	MetBuilder

Chemical Formula

C₃₉H₇₉N₂O₆P

Average Molecular Weight

703.043

Monoisotopic Molecular Weight

702.56757527

IUPAC Name

(2-{[(2S,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)C(O)\C=C\CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38?/m0/s1

InChI Key

RWKUXQNLWDTSLO-CKERXABUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Phosphosphingolipids

Alternative Parents

Substituents

Sphingoid-1-phosphate or derivatives
Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
N-acyl-amine
Fatty amide
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Axon
Cell membrane
Endosome
Membrane
Myelin sheath

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.12	ALOGPS
logP	6.98	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.92 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	213.94 m³·mol⁻¹	ChemAxon
Polarizability	87.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Axon
Cell membrane
Endosome
Membrane
Myelin sheath

Biospecimen Locations

All Tissues
Blood
Liver
Longissimus Thoracis Muscle
Placenta
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24630653	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 20647382	details
Blood	Detected and Quantified	68 +/- 10 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected and Quantified	22 +/- 7 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	3 +/- 1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	0.01 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.003 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.002 +/- 0.006 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.04 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.04 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.006 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.003 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.002 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.011 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.01 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.75 +/- 0.62 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	2.45 +/- 0.71 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	42 +/- 6 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for SM(d18:1/16:0) (BMDB0010169)

Structure for BMDB0010169 (SM(d18:1/16:0))