Milk Composition Database: Showing metabocard for SM(d18:0/18:1(9Z)) (BMDB0012089)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:32:05 UTC

Update Date

2020-06-04 19:56:12 UTC

MCDB ID

BMDB0012089

Secondary Accession Numbers

BMDB12089

Metabolite Identification

Common Name

SM(d18:0/18:1(9Z))

Description

SM(D18:0/18:1(9Z)), also known as C18:1DH sphingomyelin, 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. Thus, SM(D18:0/18:1(9Z)) is considered to be a phosphosphingolipid lipid molecule. SM(D18:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Sphingomyelin	MetBuilder
N-(9Z-Octadecenoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(D18:0/18:1(9Z))	MetBuilder
N-(9Z-Octadecenoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(9Z-Octadecenoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder

Chemical Formula

C₄₁H₈₃N₂O₆P

Average Molecular Weight

731.097

Monoisotopic Molecular Weight

730.598875399

IUPAC Name

(2-{[(2S)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadecyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadecyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,39-40,44H,6-19,22-38H2,1-5H3,(H-,42,45,46,47)/b21-20-/t39-,40?/m0/s1

InChI Key

XYLWKHKCYHMVMA-RUMIPHAVSA-N

Chemical Taxonomy

Classification

Not classified

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	5.41	ALOGPS
logP	7.71	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	38	ChemAxon
Refractivity	223.3 m³·mol⁻¹	ChemAxon
Polarizability	92.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001s-6030190400-17b9b53a12286d3eaba2	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2080191000-a473081811027a912f97	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-6090012000-25e7d04950bfc0c25559	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0010004900-ee6bea26269be0778389	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1051039200-806fdf085b442284c250	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-9182020000-e2a17725e2416df31a52	2019-02-23	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	1.04 +/- 0.02 uM	PMID: 30994344	details
Detected and Quantified	1.09 +/- 0.03 uM	PMID: 30994344	details
Detected and Quantified	1.19 +/- 0.02 uM	PMID: 30994344	details
Detected and Quantified	1.13 +/- 0.01 uM	PMID: 30994344	details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for SM(d18:0/18:1(9Z)) (BMDB0012089)

Structure for BMDB0012089 (SM(d18:0/18:1(9Z)))