Bovine Metabolome Database: Showing metabocard for PS(18:3(9Z,12Z,15Z)/14:1(9Z)) (BMDB0012408)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:37:55 UTC

Update Date

2020-05-11 20:26:41 UTC

BMDB ID

BMDB0012408

Secondary Accession Numbers

BMDB12408

Metabolite Identification

Common Name

PS(18:3(9Z,12Z,15Z)/14:1(9Z))

Description

PS(18:3(9Z,12Z,15Z)/14:1(9Z)) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PS(18:3(9Z,12Z,15Z)/14:1(9Z)), in particular, consists of one 9Z,12Z,15Z-octadecatrienoyl chain to the C-1 atom, and one 9Z-tetradecenoyl to the C-2 atom. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-a-Linolenoyl-2-myristoleoyl-sn-glycero-3-phosphoserine	HMDB
1-alpha-Linolenoyl-2-myristoleoyl-sn-glycero-3-phosphoserine	HMDB
Phosphatidylserine(18:3/14:1)	HMDB
Phosphatidylserine(18:3n3/14:1n5)	HMDB
Phosphatidylserine(18:3W3/14:1W5)	HMDB
Phosphatidylserine(32:4)	HMDB
PS(18:3/14:1)	HMDB
PS(18:3N3/14:1N5)	HMDB
PS(18:3W3/14:1W5)	HMDB
PS(32:4)	HMDB
pSer(18:3/14:1)	HMDB
pSer(18:3n3/14:1n5)	HMDB
pSer(18:3W3/14:1W5)	HMDB
pSer(32:4)	HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphoserine	HMDB
PS(18:3(9Z,12Z,15Z)/14:1(9Z))	Lipid Annotator

Chemical Formula

C₃₈H₆₆NO₁₀P

Average Molecular Weight

727.9051

Monoisotopic Molecular Weight

727.442433849

IUPAC Name

(2S)-2-amino-3-({hydroxy[(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[hydroxy(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxyphosphoryl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCC)C(O)=O

InChI Identifier

InChI=1S/C38H66NO10P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-19-14-12-10-8-6-4-2/h5,7,10-13,16-17,34-35H,3-4,6,8-9,14-15,18-33,39H2,1-2H3,(H,42,43)(H,44,45)/b7-5-,12-10-,13-11-,17-16-/t34-,35+/m1/s1

InChI Key

FMGPGIMIGMLEBQ-JHJZYHDZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoserines

Direct Parent

Phosphatidylserines

Alternative Parents

Substituents

Diacyl-glycerol-3-phosphoserine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Primary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoserines (LMGP03010400 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Intracellular membrane
Membrane

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	4.09	ALOGPS
logP	8.05	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	171.68 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	201.3 m³·mol⁻¹	ChemAxon
Polarizability	82.2 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

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001q-0000099900-9e6c17982fdc56ae95aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000y-0900099900-9299a72e76027c634b6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000y-0900099900-9299a72e76027c634b6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000010900-493f985a37752f287013	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-0011291400-634c65e493fd1880dc96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0011291100-7c41102f37878514a2c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-d749c423e348de08a1c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000001900-916d75e720d968676f93	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0195506400-ce2c3932ceff062849d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0w29-0000016900-1f49f2701902cb8f4836	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000002900-0b50db78a93d891fe455	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0090033100-6a94b8c704edb16eb4a5	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Brain
Heart
Kidney
Liver

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
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Heart	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0012408

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029024

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

52925510

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 PS(18:3(9Z,12Z,15Z)/14:1(9Z)) (BMDB0012408)

Structure for BMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))