ChemFOnt: Showing chemical card for N-hexadecanoylsphinganine-1-phosphocholine (CFc000043077)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:57 UTC

Chemfont ID

CFc000043077

Molecule Identification

Common Name

N-hexadecanoylsphinganine-1-phosphocholine

Definition

N-hexadecanoylsphinganine-1-phosphocholine is also known as Palmitoyl dihydrosphingomyelin or SM(18:0/16:0). N-hexadecanoylsphinganine-1-phosphocholine is considered to be practically insoluble (in water) and acidic. N-hexadecanoylsphinganine-1-phosphocholine is a phosphosphingolipid lipid molecule

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3R)-3-Hydroxy-2-(palmitoylamino)octadecyl 2-(trimethylazaniumyl)ethyl phosphate	HMDB, ChEBI
(2S,3R)-3-Hydroxy-2-(palmitoylamino)octadecyl 2-(trimethylazaniumyl)ethyl phosphoric acid	HMDB, Generator
C16 Dihydrosphingomyelin	HMDB, ChEBI
N-(Hexadecanoyl)-sphinganine-1-phosphocholine	HMDB, ChEBI
N-Hexadecanoyl-sphinganine-1-phosphocholine	HMDB, ChEBI
N-Hexadecanoyldihydroceramide-1-phosphocholine	HMDB, ChEBI
N-Palmitoyldihydroceramide-1-phosphocholine	HMDB, ChEBI
N-Palmitoylsphinganine-1-phosphocholine	HMDB, ChEBI
Palmitoyl dihydrosphingomyelin	HMDB, ChEBI
Palmitoyl dihydrosphingomyelin (d18:0/16:0)	HMDB, ChEBI
SM(18:0/16:0)	HMDB, ChEBI
SM(d18:0/16:0)	HMDB, ChEBI
Sphingomyelin (d18:0/16:0)	HMDB, ChEBI
{[(2S,3R)-2-hexadecanamido-3-hydroxyoctadecyl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinate	HMDB, Generator
{[(2S,3R)-2-hexadecanamido-3-hydroxyoctadecyl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid	HMDB, ChEBI
N-Palmitoyldihydrosphingomyelin	HMDB
Palmitoyldihydrosphingomyelin	HMDB
Sphingomyelin	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(d18:0/16:0)	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(Hexadecanoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder
16:0 Dihydrosphingomyelin	HMDB
C16-Dihydrosphingomyelin	HMDB
Dihydrosphingomyelin C16:0	HMDB
SM d18:0/16:0	HMDB
Sphingomyelin (d18:0,C16:0)	HMDB

Chemical Formula

C₃₉H₈₁N₂O₆P

Average Molecular Weight

705.059

Monoisotopic Molecular Weight

704.583225334

IUPAC Name

(2-{[(2S,3R)-2-hexadecanamido-3-hydroxyoctadecyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R)-2-hexadecanamido-3-hydroxyoctadecyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

60322-02-3

SMILES

[H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCCCCCCCCCCCCC)[C@H](O)CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C39H81N2O6P/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/h37-38,42H,6-36H2,1-5H3,(H-,40,43,44,45)/t37-,38+/m0/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acylsphinganine-1-phosphocholine (CHEBI:78647 )
sphingomyelin 34:0 (CHEBI:78647 )
Ceramide phosphocholines (sphingomyelins) (LMSP03010004 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062665)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.1e-05 g/L	ALOGPS
logP	5.12	ALOGPS
logP	7.18	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	-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	37	ChemAxon
Refractivity	212.98 m³·mol⁻¹	ChemAxon
Polarizability	89.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010168

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027351

KNApSAcK ID

Not Available

Chemspider ID

8115586

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9939965

PDB ID

Not Available

ChEBI ID

78647

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-hexadecanoylsphinganine-1-phosphocholine (CFc000043077)

MOL for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

3D MOL for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

3D SDF for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

3D-SDF for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

PDB for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

3D PDB for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

SMILES for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

INCHI for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

Structure for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)

3D Structure for CFc000043077 (N-hexadecanoylsphinganine-1-phosphocholine)