Bovine Metabolome Database: Showing metabocard for PS(18:2(9Z,12Z)/18:2(9Z,12Z)) (BMDB0012402)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-10-03 18:37:47 UTC

Update Date

2020-05-21 16:28:20 UTC

BMDB ID

BMDB0012402

Secondary Accession Numbers

BMDB12402

Metabolite Identification

Common Name

PS(18:2(9Z,12Z)/18:2(9Z,12Z))

Description

PS(18:2(9Z,12Z)/18:2(9Z,12Z)), also known as ps(18:2(9z,12z)/18:2(9z,12z)) or PS(18:2/18:2), 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. Thus, PS(18:2(9Z,12Z)/18:2(9Z,12Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:2(9Z,12Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:2(9Z,12Z)/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:2(9Z,12Z)/18:2(9Z,12Z)) can be biosynthesized from PC(18:2(9Z,12Z)/18:2(9Z,12Z)) and L-serine; which is mediated by the enzyme phosphatidylserine synthase. Furthermore, PS(18:2(9Z,12Z)/18:2(9Z,12Z)) can be converted into PE(18:2(9Z,12Z)/18:2(9Z,12Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Finally, PS(18:2(9Z,12Z)/18:2(9Z,12Z)) can be converted into PE(18:2(9Z,12Z)/18:2(9Z,12Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/18:2(9Z,12Z)) pathway and phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dilinoleoyl-rac-glycero-3-phosphoserine	HMDB
Phosphatidylserine(18:2/18:2)	HMDB
Phosphatidylserine(18:2n6/18:2n6)	HMDB
Phosphatidylserine(18:2W6/18:2W6)	HMDB
Phosphatidylserine(36:4)	HMDB
PS(18:2/18:2)	HMDB
PS(18:2N6/18:2N6)	HMDB
PS(18:2W6/18:2W6)	HMDB
PS(36:4)	HMDB
pSer(18:2/18:2)	HMDB
pSer(18:2n6/18:2n6)	HMDB
pSer(18:2W6/18:2W6)	HMDB
pSer(36:4)	HMDB
1,2-Di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phosphoserine	HMDB
PS(18:2(9Z,12Z)/18:2(9Z,12Z))	Lipid Annotator

Chemical Formula

C₄₂H₇₄NO₁₀P

Average Molecular Weight

784.0114

Monoisotopic Molecular Weight

783.505034105

IUPAC Name

(2S)-2-amino-3-({[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]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/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)C(O)=O

InChI Identifier

InChI=1S/C42H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,38-39H,3-10,15-16,21-37,43H2,1-2H3,(H,46,47)(H,48,49)/b13-11-,14-12-,19-17-,20-18-/t38-,39+/m1/s1

InChI Key

ZTNFQEXYTMNFHG-SOFXVBFTSA-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 (LMGP03010023 )

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	4.79	ALOGPS
logP	9.82	ChemAxon
logS	-7	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	40	ChemAxon
Refractivity	219.7 m³·mol⁻¹	ChemAxon
Polarizability	90.72 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	splash10-000i-9020130400-d5e0aa01492a4bd96148	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9010000000-d993d70970ba7f4fc3a7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-9023021100-74dbf6084ed89c1f3616	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03gi-2190032300-f17a6981ab121514c69b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-5290110100-cd9972765519661caa8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9110100000-50ac89deeca60f5f4e3c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udq-0000040900-0e7a4f3fdcae58803c49	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6y-0400040900-5e8d61708e9836d6fb43	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6y-0400040900-5e8d61708e9836d6fb43	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-0000010690-5a9e0fb6c24df326a527	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000000290-493620f05d7e59a6c200	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0090011310-c12792ef4795d12ecae6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-2f4aa19fa103b88ee08f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0000001900-66dbd27d004f199196ef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00nb-0160709600-774b40cf2068e79b724a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000010900-0f4be97706923cd4a4a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-0001091400-ec6e84b16d42bd1b9f5e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0001091100-f201f398eeaaf58ec483	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

All Tissues
Brain
Heart
Kidney
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))		Not Available

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

HMDB0012402

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029018

KNApSAcK ID

Not Available

Chemspider ID

7826036

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9547086

PDB ID

Not Available

ChEBI ID

88488

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Phosphatidylserine decarboxylase proenzyme, mitochondrial

General function:: Not Available
Specific function:: Catalyzes the formation of phosphatidylethanolamine (PtdEtn) from phosphatidylserine (PtdSer). Plays a central role in phospholipid metabolism and in the interorganelle trafficking of phosphatidylserine.
Gene Name:: PISD
Uniprot ID:: Q58DH2
Molecular weight:: 47244.0

Reactions

PS(18:2(9Z,12Z)/18:2(9Z,12Z)) → PE(18:2(9Z,12Z)/18:2(9Z,12Z)) + Carbon dioxide	details

Enzyme Details

2. Phosphatidylserine synthase 1

General function:: Not Available
Specific function:: Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:: PTDSS1
Uniprot ID:: Q2KHY9
Molecular weight:: 55416.0

Reactions

PC(18:2(9Z,12Z)/18:2(9Z,12Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/18:2(9Z,12Z))	details

Showing metabocard for PS(18:2(9Z,12Z)/18:2(9Z,12Z)) (BMDB0012402)

Structure for BMDB0012402 (PS(18:2(9Z,12Z)/18:2(9Z,12Z)))

Enzymes

Reactions

Reactions