创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-09-14 15:20:01 UTC
描述
Phosphoserine is the phosphoric acid ester of the amino acid serine. It is found in essentially all living organisms ranging from microbes to plants to mammals. Phosphoserine is a component of many proteins as the result of posttranslational modifications to the native protein’s serine residue(s). The phosphorylation of the hydroxyl functional group in serine to produce phosphoserine is catalyzed by various types of kinases. Serine is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Free phosphoserine is found in many biofluids and likely arises from the proteolysis of proteins containing phosphoserine residues (PMID: 7693088).
同义词
1:(+)-L-Serine dihydrogen phosphate (ester)
2:(2S)-2-Amino-3-(phosphonooxy)propanoic acid
3:(S)-2-Amino-3-hydroxypropanoic acid 3-phosphate
4:3-Phosphoserine
5:Dexfosfoserine
6:L-O-Phosphoserine
7:O-Phosphoserine
8:3-Phospho-L-serine
9:(+)-L-Serine dihydrogen phosphoric acid (ester)
10:(2S)-2-Amino-3-(phosphonooxy)propanoate
11:(S)-2-Amino-3-hydroxypropanoate 3-phosphate
12:(S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acid
13:3-O-Phosphoserine
14:Fosforina
15:L-3-Phosphoserine
16:L-O-Serine phosphate
17:L-Phosphoserine
18:L-Serine dihydrogen phosphate (ester)
19:L-Serine phosphate
20:L-Serinephosphorate
21:L-Serinephosphoric acid
22:L-Seryl phosphate
23:Plasmenylserine
化学名称
(2S)-2-amino-3-(phosphonooxy)propanoic acid
代谢物结构字符串
N[C@@H](COP(O)(O)=O)C(O)=O
inchi标识符
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
印记键
BZQFBWGGLXLEPQ-REOHCLBHSA-N
分类学
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.
description:L-alpha-amino acids
kingdom:Organic compounds
super_class:Organic acids and derivatives
class:Carboxylic acids and derivatives
sub_class:Amino acids, peptides, and analogues
molecular_framework:Aliphatic acyclic compounds
1:Amino acids
2:Carbonyl compounds
3:Carboxylic acids
4:Hydrocarbon derivatives
5:Monoalkyl phosphates
6:Monoalkylamines
7:Monocarboxylic acids and derivatives
8:Organic oxides
9:Organopnictogen compounds
10:Phosphoethanolamines
11:Aliphatic acyclic compound
12:Alkyl phosphate
13:Amine
14:Amino acid
15:Carbonyl group
16:Carboxylic acid
17:Hydrocarbon derivative
18:L-alpha-amino acid
19:Monoalkyl phosphate
20:Monocarboxylic acid or derivatives
21:Organic nitrogen compound
22:Organic oxide
23:Organic oxygen compound
24:Organic phosphoric acid derivative
25:Organonitrogen compound
26:Organooxygen compound
27:Organopnictogen compound
28:Phosphoethanolamine
29:Phosphoric acid ester
30:Primary aliphatic amine
31:Primary amine
32:O-phosphoserine
本体论
term:Disposition
definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.
parent_id:
level:1
type:parent
term:Source
definition:Natural or synthetic origin of a chemical.
parent_id:7724
*level:2
type:parent
term:Endogenous
definition:
parent_id:7735
**level:3
type:child
term:Biological location
definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.
parent_id:7724
*level:2
type:parent
term:Organ and components
definition:An anatomical organizational level including multiple tissues or substructures, which enables a common biological function.
parent_id:7725
**level:3
type:parent
term:Prostate
definition:The male reproductive accessory gland that produces prostatic fluid and is located adjacent to or around the urethra distal to the urinary bladder in mammals. (nci).
parent_id:7727
***level:4
type:child
synonym:Prostate gland
term:Biofluid and excreta
definition:A liquid, semi-solid or solid material originating in the body.
parent_id:7725
**level:3
type:parent
term:Urine
definition:Excretion in liquid state processed by the kidney.
parent_id:7731
***level:4
type:child
term:Blood
definition:A liquid tissue with the primary function of transporting oxygen and carbon dioxide (nci). it supplies the tissues with nutrients, removes waste products, and contains various components of the immune system defending the body against infection.
parent_id:7731
***level:4
type:child
term:Cerebrospinal fluid
definition:The fluid that is contained within the brain ventricles, the subarachnoid space and the central canal of the spinal cord. (nci).
parent_id:7731
***level:4
type:child
synonym:Csf
term:Subcellular
definition:An anatomical organizational level including a component within a biological cell .
parent_id:7725
**level:3
type:parent
term:Cytoplasm
definition:The portion of the cell contained within the plasma membrane but excluding the nucleus.
parent_id:7730
***level:4
type:child
synonym:Cytoplasma
term:Process
definition:Biological or chemical events, or a series thereof, leading to a known function or end-product.
parent_id:
level:1
type:parent
term:Naturally occurring process
definition:Naturally-occurring molecular events or a series thereof, leading to a known function or end-product.
parent_id:7659
*level:2
type:parent
term:Biological process
definition:Biological or chemical events or a series thereof, leading to a known function or end-product within an organism.
parent_id:7660
**level:3
type:parent
term:Biochemical pathway
definition:A linked series of chemical reactions that occur in a defined order within or between organism cells, and lead to a known function or end product.
parent_id:7661
***level:4
type:parent
term:Role
definition:The purpose or function assumed by a chemical, either naturally or as intended by humans .
parent_id:
level:1
type:parent
term:Industrial application
definition:The assumed function of a chemical utilized by human.
parent_id:7671
*level:2
type:parent
term:Pharmaceutical industry
definition:A pharmacologic activity for which a chemical substance is utilized owing to its biological role.
parent_id:7678
**level:3
type:parent
term:Pharmaceutical
definition:
parent_id:7679
***level:4
type:child
实验性质
1:
kind:water_solubility
value:71 mg/mL
source:
2:
kind:melting_point
value:170 - 171 °C
source:
预测性质
1:
kind:logp
value:-2.32
source:ALOGPS
2:
kind:logs
value:-0.97
source:ALOGPS
3:
kind:solubility
value:19.9 g/L
source:ALOGPS
4:
kind:logp
value:-3.2
source:ChemAxon
5:
kind:pka_strongest_acidic
value:1.2
source:ChemAxon
6:
kind:pka_strongest_basic
value:9.39
source:ChemAxon
7:
kind:iupac
value:(2S)-2-amino-3-(phosphonooxy)propanoic acid
source:ChemAxon
8:
kind:average_mass
value:185.0725
source:ChemAxon
9:
kind:mono_mass
value:185.008923505
source:ChemAxon
10:
kind:smiles
value:N[C@@H](COP(O)(O)=O)C(O)=O
source:ChemAxon
11:
kind:formula
value:C3H8NO6P
source:ChemAxon
12:
kind:inchi
value: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
source:ChemAxon
13:
kind:inchikey
value:BZQFBWGGLXLEPQ-REOHCLBHSA-N
source:ChemAxon
14:
kind:polar_surface_area
value:130.08
source:ChemAxon
15:
kind:refractivity
value:32.91
source:ChemAxon
16:
kind:polarizability
value:13.97
source:ChemAxon
17:
kind:rotatable_bond_count
value:4
source:ChemAxon
18:
kind:acceptor_count
value:6
source:ChemAxon
19:
kind:donor_count
value:4
source:ChemAxon
20:
kind:physiological_charge
value:-2
source:ChemAxon
21:
kind:formal_charge
value:0
source:ChemAxon
22:
kind:number_of_rings
value:0
source:ChemAxon
23:
kind:bioavailability
value:Yes
source:ChemAxon
24:
kind:rule_of_five
value:Yes
source:ChemAxon
25:
kind:ghose_filter
value:No
source:ChemAxon
26:
kind:veber_rule
value:No
source:ChemAxon
27:
kind:mddr_like_rule
value:No
source:ChemAxon
1:
type:Specdb::NmrTwoD
spectrum_id:1251
2:
type:Specdb::CMs
spectrum_id:509
3:
type:Specdb::CMs
spectrum_id:510
4:
type:Specdb::CMs
spectrum_id:511
5:
type:Specdb::CMs
spectrum_id:1492
6:
type:Specdb::CMs
spectrum_id:2586
7:
type:Specdb::CMs
spectrum_id:30393
8:
type:Specdb::CMs
spectrum_id:30394
9:
type:Specdb::CMs
spectrum_id:30657
10:
type:Specdb::CMs
spectrum_id:31111
11:
type:Specdb::CMs
spectrum_id:32179
12:
type:Specdb::CMs
spectrum_id:32180
13:
type:Specdb::CMs
spectrum_id:37396
14:
type:Specdb::CMs
spectrum_id:136676
15:
type:Specdb::CMs
spectrum_id:144410
16:
type:Specdb::NmrOneD
spectrum_id:1308
17:
type:Specdb::NmrOneD
spectrum_id:4960
18:
type:Specdb::NmrOneD
spectrum_id:4961
19:
type:Specdb::NmrOneD
spectrum_id:6362
20:
type:Specdb::NmrOneD
spectrum_id:6363
21:
type:Specdb::NmrOneD
spectrum_id:6364
22:
type:Specdb::NmrOneD
spectrum_id:6365
23:
type:Specdb::NmrOneD
spectrum_id:6366
24:
type:Specdb::NmrOneD
spectrum_id:6367
25:
type:Specdb::NmrOneD
spectrum_id:6368
26:
type:Specdb::NmrOneD
spectrum_id:6369
27:
type:Specdb::NmrOneD
spectrum_id:6370
28:
type:Specdb::NmrOneD
spectrum_id:6371
29:
type:Specdb::NmrOneD
spectrum_id:6372
30:
type:Specdb::NmrOneD
spectrum_id:6373
31:
type:Specdb::NmrOneD
spectrum_id:6374
32:
type:Specdb::NmrOneD
spectrum_id:6375
33:
type:Specdb::NmrOneD
spectrum_id:6376
34:
type:Specdb::NmrOneD
spectrum_id:6377
35:
type:Specdb::NmrOneD
spectrum_id:6378
36:
type:Specdb::NmrOneD
spectrum_id:6379
37:
type:Specdb::NmrOneD
spectrum_id:6380
38:
type:Specdb::NmrOneD
spectrum_id:6381
39:
type:Specdb::MsMs
spectrum_id:475
40:
type:Specdb::MsMs
spectrum_id:476
41:
type:Specdb::MsMs
spectrum_id:477
42:
type:Specdb::MsMs
spectrum_id:3895
43:
type:Specdb::MsMs
spectrum_id:3896
44:
type:Specdb::MsMs
spectrum_id:3897
45:
type:Specdb::MsMs
spectrum_id:3898
46:
type:Specdb::MsMs
spectrum_id:3899
47:
type:Specdb::MsMs
spectrum_id:3903
48:
type:Specdb::MsMs
spectrum_id:178479
49:
type:Specdb::MsMs
spectrum_id:178480
50:
type:Specdb::MsMs
spectrum_id:178481
51:
type:Specdb::MsMs
spectrum_id:180798
52:
type:Specdb::MsMs
spectrum_id:180799
53:
type:Specdb::MsMs
spectrum_id:180800
54:
type:Specdb::MsMs
spectrum_id:439096
55:
type:Specdb::MsMs
spectrum_id:446797
56:
type:Specdb::MsMs
spectrum_id:446798
57:
type:Specdb::MsMs
spectrum_id:446799
58:
type:Specdb::MsMs
spectrum_id:446800
59:
type:Specdb::MsMs
spectrum_id:446801
60:
type:Specdb::MsMs
spectrum_id:2226435
61:
type:Specdb::MsMs
spectrum_id:2228262
62:
type:Specdb::MsMs
spectrum_id:2228800
63:
type:Specdb::MsMs
spectrum_id:2230666
生物学性质
1:
cellular:(1):Cytoplasm
2:
biospecimen:(1):Blood
biospecimen:(2):Cerebrospinal Fluid (CSF)
biospecimen:(3):Urine
3:
tissue:(1):Prostate
4:
[1]:
name:3-Phosphoglycerate dehydrogenase deficiency
smpdb_id:SMP00721
kegg_map_id:
[2]:
name:Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
smpdb_id:SMP00179
kegg_map_id:
[3]:
name:Dimethylglycine Dehydrogenase Deficiency
smpdb_id:SMP00242
kegg_map_id:
[4]:
name:Dimethylglycine Dehydrogenase Deficiency
smpdb_id:SMP00484
kegg_map_id:
[5]:
name:Glycine, serine and threonine metabolism
smpdb_id:
kegg_map_id:map00260
[6]:
name:Hyperglycinemia, non-ketotic
smpdb_id:SMP00485
kegg_map_id:
[7]:
name:Non Ketotic Hyperglycinemia
smpdb_id:SMP00223
kegg_map_id:
[8]:
name:Sarcosinemia
smpdb_id:SMP00244
kegg_map_id:
正常浓度
1:
biospecimen:Blood
concentration_value:17.0 +/- 3.0
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
2:
biospecimen:Cerebrospinal Fluid (CSF)
concentration_value:4.2 +/- 1.7
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
3:
biospecimen:Cerebrospinal Fluid (CSF)
concentration_value:5.0 +/- 0.9
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
4:
biospecimen:Urine
concentration_value:<0.11
concentration_units:umol/mmol creatinine
subject_age:Adolescent (13-18 years old)
subject_sex:Not Specified
subject_condition:Normal
5:
biospecimen:Urine
concentration_value:59.051 +/- 21.239
concentration_units:umol/mmol creatinine
subject_age:Children (1 - 13 years old)
subject_sex:Not Specified
subject_condition:Normal
6:
biospecimen:Urine
concentration_value:<0.11
concentration_units:umol/mmol creatinine
subject_age:Adult (>18 years old)
subject_sex:Not Specified
subject_condition:Normal
7:
biospecimen:Urine
concentration_value:<0.113
concentration_units:umol/mmol creatinine
subject_age:Infant (0-1 year old)
subject_sex:Not Specified
subject_condition:Normal
8:
biospecimen:Urine
concentration_value:<0.11
concentration_units:umol/mmol creatinine
subject_age:Children (1-13 years old)
subject_sex:Not Specified
subject_condition:Normal
9:
biospecimen:Urine
concentration_value:4.605 (1.645-7.566)
concentration_units:umol/mmol creatinine
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
10:
biospecimen:Urine
concentration_value:<0.11
concentration_units:umol/mmol creatinine
subject_age:Children (1-13 years old)
subject_sex:Not Specified
subject_condition:Normal
11:
biospecimen:Urine
concentration_value:2.0 (0.53-3.28)
concentration_units:umol/mmol creatinine
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
12:
biospecimen:Urine
concentration_value:6.0 (2.71-10.4)
concentration_units:umol/mmol creatinine
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
13:
biospecimen:Urine
concentration_value:<0.11
concentration_units:umol/mmol creatinine
subject_age:Children (1-13 years old)
subject_sex:Not Specified
subject_condition:Normal
异常浓度
1:
biospecimen:Urine
concentration_value:146.693 +/- 9.722
concentration_units:umol/mmol creatinine
patient_age:Children (1 - 13 years old)
patient_sex:Not Specified
patient_information:Eosinophilic esophagitis
疾病参考
1:
name:Eosinophilic esophagitis
omim_id:610247
[1]:
reference_text:Mordechai, Hien, and David S. Wishart
pubmed_id:
综合参考
Barruel, Elena Mery. Biosynthesis of phosphoserine in vitro. Anales Fac. Quim. y Farm. (1960), 12 228-33.
一般参考
1:
protein_accession:HMDBP00851
name:Phosphoserine aminotransferase
uniprot_id:Q9Y617
gene_name:PSAT1
protein_type:Enzyme
2:
protein_accession:HMDBP00887
name:Phosphoserine phosphatase
uniprot_id:P78330
gene_name:PSPH
protein_type:Unknown
蛋白质结合
1:
reference_text: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. doi: 10.1038/nature07762.
pubmed_id:19212411
2:
reference_text: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.
pubmed_id:9268238
3:
reference_text:Kataoka H, Nakai K, Katagiri Y, Makita M: Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection. Biomed Chromatogr. 1993 Jul-Aug;7(4):184-8.
pubmed_id:7693088
4:
reference_text:Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.
pubmed_id:29457794