Showing Compound DL-O-Phosphoserine (FDB022700)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:10 UTC

Update date

2020-09-17 15:40:30 UTC

Primary ID

FDB022700

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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). A serine derivative that is serine substituted at the oxygen atom by a phosphono group. 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.

CAS Number

17885-08-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
(±)-Phosphoserine	manual
2-amino-3-(Onooxy)propanoate	Generator
2-amino-3-(Onooxy)propanoic acid	ChEBI
3-O-1-Serine	HMDB
3-O-Serine	HMDB
DL-O-Orylserine	HMDB
DL-O-Oserine	HMDB
DL-O-Phosphoserine	hmdb
DL-O-Serine ate	HMDB
DL-Serine dihydrogen ate	ChEBI
DL-Serine dihydrogen ic acid	Generator
DL-Serine monoorate	HMDB
DL-Serine monooric acid	HMDB
DL-Serine, dihydrogen ate (ester)	ChEBI
DL-Serine, dihydrogen ic acid (ester)	Generator
Foserin	db_source
Monoserina	db_source
Neuroserina	db_source
O-O-DL-Serine	HMDB
O-Onoserine	HMDB
Orylserine	HMDB
P-Serine	HMDB
Serine ate	HMDB
Serine-3-ate	HMDB
Serinfosfan	db_source
Serophen?	db_source

Predicted Properties

Property	Value	Source
Water Solubility	19.9 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C3H8NO6P

IUPAC name

2-amino-3-(phosphonooxy)propanoic acid

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

Isomeric SMILES

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

Average Molecular Weight

185.0725

Monoisotopic Molecular Weight

185.008923505

Classification

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

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Epidermis

Organ and components:

Testicle

Subcellular:

Cytoplasm

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	DL-O-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9200000000-579f933727173ebf1101	Spectrum
Predicted GC-MS	DL-O-Phosphoserine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-6900000000-fbaee5e7f89c1dcb6669	Spectrum
Predicted GC-MS	DL-O-Phosphoserine, non-derivatized, 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	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dr-9000000000-c5a74679d970f7b6e2d5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-1d94e50890f1499da7f4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0002-9000000000-64c49953b5b27ea372c6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9300000000-2adf6419e88c778446e9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9200000000-04bb0aee57d7fffbcaa7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9100000000-2fb2869ecf3634b54a39	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9000000000-2c6e3412bb661c65ec10	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-9800000000-672ba3fb65a9cac25044	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-e63c25df326283cc3b7f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-dbc8b3072add030d1711	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-9800000000-10234b7ff1b336489a5a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-8a4c753dfa69ac6720e0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ebe13ec0e44d8c4f4771	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-5900000000-0165c58c1b2c713290ed	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0005-9300000000-8c803e99e72e9cb59913	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-9000000000-6ed59f8b5f83d923a8b4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9000000000-68e2a2413db514aab39e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum