Bovine Metabolome Database: Showing metabocard for DL-O-Phosphoserine (BMDB0001721)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:58 UTC

Update Date

2020-05-11 20:55:44 UTC

BMDB ID

BMDB0001721

Secondary Accession Numbers

BMDB01721

Metabolite Identification

Common Name

DL-O-Phosphoserine

Description

DL-O-Phosphoserine, also known as DL-O-phosphorylserine or DL-O-serine phosphate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). DL-O-Phosphoserine is a very strong basic compound (based on its pKa). DL-O-Phosphoserine exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-3-(phosphonooxy)propanoic acid	ChEBI
DL-Serine dihydrogen phosphate	ChEBI
DL-Serine, dihydrogen phosphate (ester)	ChEBI
Phosphoserine	ChEBI
2-Amino-3-(phosphonooxy)propanoate	Generator
DL-Serine dihydrogen phosphoric acid	Generator
DL-Serine, dihydrogen phosphoric acid (ester)	Generator
3-Phospho-1-serine	HMDB
3-Phospho-serine	HMDB
3-Phosphoserine	HMDB
DL-O-Phosphorylserine	HMDB
DL-O-Serine phosphate	HMDB
DL-Serine monophosphorate	HMDB
DL-Serine monophosphoric acid	HMDB
Energoserina	HMDB
O-Phospho-DL-serine	HMDB
O-Phospho-L-serine	HMDB
O-Phosphonoserine	HMDB
p-Serine	HMDB
Phosphorylserine	HMDB
Serine phosphate	HMDB
Serine-3-phosphate	HMDB
Serophen	HMDB
Phosphate, seryl	HMDB
Seryl phosphate	HMDB
Phosphate, serine	HMDB

Chemical Formula

C₃H₈NO₆P

Average Molecular Weight

185.0725

Monoisotopic Molecular Weight

185.008923505

IUPAC Name

2-amino-3-(phosphonooxy)propanoic acid

Traditional Name

P-serine

CAS Registry Number

17885-08-4

SMILES

NC(COP(O)(O)=O)C(O)=O

InChI Identifier

InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)

InChI Key

BZQFBWGGLXLEPQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Phosphoethanolamine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:37712 )
O-phosphoamino acid (CHEBI:37712 )
serine derivative (CHEBI:37712 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	228 °C	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	-2.3	ALOGPS
logP	-3.2	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Acidic)	1.2	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	130.08 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	32.91 m³·mol⁻¹	ChemAxon
Polarizability	14.01 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

Cytoplasm

Biospecimen Locations

Epidermis
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001721

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022700

KNApSAcK ID

Not Available

Chemspider ID

104

KEGG Compound ID

C01005

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

37712

References

Synthesis Reference

Lacombe J M; Andriamanampisoa F; Pavia A A Solid-phase synthesis of peptides containing phosphoserine using phosphate tert.-butyl protecting group. International journal of peptide and protein research (1990), 36(3), 275-80.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 14-3-3 protein zeta/delta

General function:: Involved in protein domain specific binding
Specific function:: Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Activates the ADP-ribosyltransferase (exoS) activity of bacterial origin. Induces ARHGEF7 activity on RAC1 as well as lamellipodia and membrane ruffle formation (By similarity). In neurons, regulates spine maturation through the modulation of ARHGEF7 activity (By similarity).
Gene Name:: YWHAZ
Uniprot ID:: P63103
Molecular weight:: 27745.0

Enzyme Details

2. 14-3-3 protein eta

General function:: Involved in protein domain specific binding
Specific function:: Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Negatively regulates the kinase activity of PDPK1 (By similarity).
Gene Name:: YWHAH
Uniprot ID:: P68509
Molecular weight:: 28212.0

Enzyme Details

3. 14-3-3 protein gamma

General function:: Involved in insulin-like growth factor receptor binding
Specific function:: Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner.
Gene Name:: YWHAG
Uniprot ID:: P68252
Molecular weight:: 28253.0

Enzyme Details

4. 14-3-3 protein beta/alpha

General function:: Involved in protein domain specific binding
Specific function:: Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Negative regulator of osteogenesis. Blocks the nuclear translocation of the phosphorylated form (by AKT1) of SRPK2 and antagonizes its stimulatory effect on cyclin D1 expression resulting in blockage of neuronal apoptosis elicited by SRPK2. Negative regulator of signaling cascades that mediate activation of MAP kinases via AKAP13.
Gene Name:: YWHAB
Uniprot ID:: P68250
Molecular weight:: 28081.0

Enzyme Details

5. Phosphoserine aminotransferase

General function:: Coenzyme transport and metabolism
Specific function:: Not Available
Gene Name:: PSAT1
Uniprot ID:: A6QR28
Molecular weight:: 40529.0

Enzyme Details

6. 14-3-3 protein theta

General function:: Involved in protein domain specific binding
Specific function:: Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Negatively regulates the kinase activity of PDPK1 (By similarity).
Gene Name:: YWHAQ
Uniprot ID:: Q3SZI4
Molecular weight:: 27764.0

Enzyme Details

7. 14-3-3 protein epsilon

General function:: Not Available
Specific function:: Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways (PubMed:7931346). Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif (PubMed:7931346). Binding generally results in the modulation of the activity of the binding partner (PubMed:7931346). Positively regulates phosphorylated protein HSF1 nuclear export to the cytoplasm (By similarity).
Gene Name:: YWHAE
Uniprot ID:: P62261
Molecular weight:: 29174.0

Enzyme Details

8. 14-3-3 protein sigma

General function:: Involved in protein domain specific binding
Specific function:: Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. When bound to KRT17, regulates protein synthesis and epithelial cell growth by stimulating Akt/mTOR pathway. May also regulate MDM2 autoubiquitination and degradation and thereby activate p53/TP53 (By similarity).
Gene Name:: SFN
Uniprot ID:: Q0VC36
Molecular weight:: 27849.0

Showing metabocard for DL-O-Phosphoserine (BMDB0001721)

Structure for BMDB0001721 (DL-O-Phosphoserine)

Enzymes