Cannabis Compound Database: Showing Compound Card for Phosphoserine (CDB004833)

Jump To Section:

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

Record Information

Version

1.0

Created at

2020-04-17 18:41:28 UTC

Updated at

2020-11-18 16:38:48 UTC

CannabisDB ID

CDB004833

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Phosphoserine

Description

Phosphoserine, also known as dexfosfoserine or fosforina, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. The L-enantiomer of O-phosphoserine. Phosphoserine is a very strong basic compound (based on its pKa). Phosphoserine exists in all living species, ranging from bacteria to humans. Within humans, phosphoserine participates in a number of enzymatic reactions. In particular, phosphoserine and oxoglutaric acid can be biosynthesized from phosphohydroxypyruvic acid and L-glutamic acid; which is catalyzed by the enzyme phosphoserine aminotransferase. In addition, phosphoserine can be converted into L-serine; which is mediated by the enzyme phosphoserine phosphatase. In humans, phosphoserine is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Phosphoserine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(+)-L-Serine dihydrogen phosphate (ester)	ChEBI
(2S)-2-Amino-3-(phosphonooxy)propanoic acid	ChEBI
(S)-2-Amino-3-hydroxypropanoic acid 3-phosphate	ChEBI
3-Phosphoserine	ChEBI
Dexfosfoserine	ChEBI
L-O-Phosphoserine	ChEBI
O-Phosphoserine	ChEBI
3-Phospho-L-serine	Kegg
(+)-L-Serine dihydrogen phosphoric acid (ester)	Generator
(2S)-2-Amino-3-(phosphonooxy)propanoate	Generator
(S)-2-Amino-3-hydroxypropanoate 3-phosphate	Generator
(S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acid	Generator
3-O-Phosphoserine	HMDB
Fosforina	HMDB
L-3-Phosphoserine	HMDB
L-O-Serine phosphate	HMDB
L-Phosphoserine	HMDB
L-Serine dihydrogen phosphate (ester)	HMDB
L-Serine phosphate	HMDB
L-Serinephosphorate	HMDB
L-Serinephosphoric acid	HMDB
L-Seryl phosphate	HMDB
Plasmenylserine	HMDB

Chemical Formula

C₃H₈NO₆P

Average Molecular Weight

185.07

Monoisotopic Molecular Weight

185.0089

IUPAC Name

(2S)-2-amino-3-(phosphonooxy)propanoic acid

Traditional Name

phosphoserine

CAS Registry Number

407-41-0

SMILES

N[C@@H](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)/t2-/m0/s1

InChI Key

BZQFBWGGLXLEPQ-REOHCLBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-phosphoserine (CHEBI:15811 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cytoplasm

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	170 - 171 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	71 mg/mL	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	13.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Phosphoserine, x TMS, GC-MS Spectrum	splash10-02u1-0930000000-c899f07d021f46de8c59	Spectrum
GC-MS	Phosphoserine, x TMS, GC-MS Spectrum	splash10-02am-0980000000-224ebb540cc8cfeee7bf	Spectrum
GC-MS	Phosphoserine, non-derivatized, GC-MS Spectrum	splash10-0k92-0943000000-2c96e781366647a38c1b	Spectrum
GC-MS	Phosphoserine, 4 TMS, GC-MS Spectrum	splash10-0rka-2965000000-6295c9d3aab0dbbdbe06	Spectrum
GC-MS	Phosphoserine, non-derivatized, GC-MS Spectrum	splash10-02u1-0930000000-c899f07d021f46de8c59	Spectrum
GC-MS	Phosphoserine, non-derivatized, GC-MS Spectrum	splash10-02am-0980000000-224ebb540cc8cfeee7bf	Spectrum
GC-MS	Phosphoserine, non-derivatized, GC-MS Spectrum	splash10-0k92-0943000000-2c96e781366647a38c1b	Spectrum
GC-MS	Phosphoserine, non-derivatized, GC-MS Spectrum	splash10-0rka-2965000000-6295c9d3aab0dbbdbe06	Spectrum
GC-MS	Phosphoserine, non-derivatized, GC-MS Spectrum	splash10-052b-0943000000-925dbf1f579400fe1275	Spectrum
GC-MS	Phosphoserine, non-derivatized, GC-MS Spectrum	splash10-03yl-0890000000-f853ba80cc56b6057d3e	Spectrum
Predicted GC-MS	Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9200000000-579f933727173ebf1101	Spectrum
Predicted GC-MS	Phosphoserine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9720000000-0c93ad0358d5840580e0	Spectrum
Predicted GC-MS	Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoserine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoserine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoserine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoserine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoserine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-07c4d8f30a6ca83b8b55	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dr-9000000000-c5a74679d970f7b6e2d5	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-1d94e50890f1499da7f4	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-3900000000-0424244742b82164682f	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9100000000-f86c85cff0432259c764	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00kr-9000000000-997762f62b3a2e22b12b	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9000000000-4732d51a493c7bf13c29	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00kf-9000000000-5d40f9a41d75ac08b4c2	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-9000000000-f653dafdf17fa74b83a5	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-9000000000-f653dafdf17fa74b83a5	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-3900000000-76c6900db1ecb22c9dc6	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9100000000-f86c85cff0432259c764	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00kr-9000000000-25381bf668ede8881af0	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9000000000-63cde6935414b6893a5f	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00kf-9000000000-5d40f9a41d75ac08b4c2	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-030fc19bab74121b9536	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9000000000-78dc68824c37b96fd97f	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8c715ebc5361358f572d	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000t-5900000000-2acd16447bafd738b8b2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-9800000000-672ba3fb65a9cac25044	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-e63c25df326283cc3b7f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-dbc8b3072add030d1711	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-9800000000-10234b7ff1b336489a5a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-8a4c753dfa69ac6720e0	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ebe13ec0e44d8c4f4771	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycine and Serine Metabolism
Dimethylglycine Dehydrogenase Deficiency		Not Available
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)		Not Available
Sarcosinemia		Not Available
Non Ketotic Hyperglycinemia		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Phosphoserine aminotransferase	PSAT1	9q21.2	Q9Y617	details
Phosphoserine phosphatase	PSPH	7p11.2	P78330	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000272

DrugBank ID

DB04522

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

3-phosphoserine

METLIN ID

5270

PubChem Compound

68841

PDB ID

Not Available

ChEBI ID

15811

References

General References

Not Available

Enzymes

Enzyme Details

1. Phosphoserine aminotransferase

General function:: Involved in metabolic process
Specific function:: Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:: PSAT1
Uniprot ID:: Q9Y617
Molecular weight:: 35188.305

Enzyme Details

2. Phosphoserine phosphatase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the last step in the biosynthesis of serine from carbohydrates. The reaction mechanism proceeds via the formation of a phosphoryl-enzyme intermediates.
Gene Name:: PSPH
Uniprot ID:: P78330
Molecular weight:: 25007.49

Showing Compound Card for Phosphoserine (CDB004833)

Structure for CDB004833 (Phosphoserine)

Enzymes