P. aeruginosa Metabolome Database: 3-phospho-L-serine (PAMDB110633)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110633

Identification

Name:

3-phospho-L-serine

Description:

An O-phosphonatooxyserine(2−) that is the conjugate base of O-phospho-L-serine.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

O-phospho-L-serine
L-serine phosphate
phosphoryl-L-serine
L-seryl phosphate
L-serine-3P
L-serine 3-phosphate
3-phospho-L-serine

Chemical Formula:

C₃H₆NO₆P

Average Molecular Weight:

183.06

Monoisotopic Molecular Weight:

186.0167485367

InChI Key:

BZQFBWGGLXLEPQ-REOHCLBHSA-L

InChI:

InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/p-2/t2-/m0/s1

CAS number:

407-41-0

IUPAC Name:

(2S)-2-azaniumyl-3-(phosphonatooxy)propanoate

Traditional IUPAC Name:

phosphoserine

SMILES:

C(OP([O-])([O-])=O)C([N+])C([O-])=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organic acids and derivatives

Sub Class

Carboxylic acids and derivatives

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 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

170 - 171 °C

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
Water Solubility	19.9 mg/mL	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	13.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

Pathways:

Glycine and Serine Metabolism pae00260

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)	splash10-02u1-0930000000-c899f07d021f46de8c59	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)	splash10-02am-0980000000-224ebb540cc8cfeee7bf	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0k92-0943000000-2c96e781366647a38c1b	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0rka-2965000000-6295c9d3aab0dbbdbe06	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-07c4d8f30a6ca83b8b55	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dr-9000000000-c5a74679d970f7b6e2d5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-1d94e50890f1499da7f4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-3900000000-0424244742b82164682f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9100000000-f86c85cff0432259c764	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00kr-9000000000-997762f62b3a2e22b12b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9000000000-4732d51a493c7bf13c29	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00kf-9000000000-5d40f9a41d75ac08b4c2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-9000000000-f653dafdf17fa74b83a5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
Molina JA, Jimenez-Jimenez FJ, Gomez P, Vargas C, Navarro JA, Orti-Pareja M, Gasalla T, Benito-Leon J, Bermejo F, Arenas J: Decreased cerebrospinal fluid levels of neutral and basic amino acids in patients with Parkinson's disease. J Neurol Sci. 1997 Sep 10;150(2):123-7. [9268238 ]

Synthesis Reference:

Barruel, Elena Mery. Biosynthesis of phosphoserine in vitro. Anales Fac. Quim. y Farm. (1960), 12 228-33.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CAS	407-41-0
CAS	17885-08-4
ChEBI	57524
ChemSpider	5415612
HMDB	HMDB00272
IAF1260	36594
KEGG	C01005
PubChem	7059387

3-phospho-L-serine (PAMDB110633)

Structure for 3-phospho-L-serine (PAMDB110633)