MiMeDB: Showing metabocard for D-Asparagine (MMDBc0033158)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:37:04 UTC

Update Date

2024-04-20 06:09:18 UTC

Metabolite ID

MMDBc0033158

Metabolite Identification

Common Name

D-Asparagine

Description

Asparagine (Asn) or L-asparagine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-asparagine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Asparagine is found in all organisms ranging from bacteria to plants to animals. In humans, asparagine is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. The precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. This enzyme transfers the amino group from glutamate to oxaloacetate producing alpha-ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming beta-aspartyl-AMP. Glutamine donates an ammonium group which reacts with beta-aspartyl-AMP to form asparagine and free AMP. Since the asparagine side chain can make efficient hydrogen bond interactions with the peptide backbone, asparagines are often found near the beginning and end of alpha-helices, and in turn motifs in beta sheets. Its role can be thought as "capping" the hydrogen bond interactions which would otherwise need to be satisfied by the polypeptide backbone. Asparagine also provides key sites for N-linked glycosylation, a modification of the protein chain that is characterized by the addition of carbohydrate chains. A reaction between asparagine and reducing sugars or reactive carbonyls produces acrylamide (acrylic amide) in food when heated to sufficient temperature (i.e. baking). These occur primarily in baked goods such as French fries, potato chips, and roasted coffee. Asparagine was first isolated in 1806 from asparagus juice --hence its name. Asparagine was the first amino acid to be isolated. The smell observed in the urine of some individuals after the consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. However, some scientists disagree and implicate other substances in the smell, especially methanethiol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
(2R)-2,4-Diamino-4-oxobutanoic acid	ChEBI
(2R)-2-Amino-3-carbamoylpropanoic acid	ChEBI
(R)-2-Amino-3-carbamoylpropanoic acid	ChEBI
D-2-Aminosuccinamic acid	ChEBI
D-Asparagin	ChEBI
D-Aspartic acid beta-amide	ChEBI
DSG	ChEBI
(2R)-2,4-Diamino-4-oxobutanoate	Generator
(2R)-2-Amino-3-carbamoylpropanoate	Generator
(R)-2-Amino-3-carbamoylpropanoate	Generator
D-2-Aminosuccinamate	Generator
D-Aspartate b-amide	Generator
D-Aspartate beta-amide	Generator
D-Aspartate β-amide	Generator
D-Aspartic acid b-amide	Generator
D-Aspartic acid β-amide	Generator
(R)-2-Aminosuccinamic acid	HMDB
(R)-2-Aminosuccinic acid 4-amide	HMDB
D-Aspartic acid 4-amide	HMDB

Molecular Formula

C₄H₈N₂O₃

Average Mass

132.1179

Monoisotopic Mass

132.053492132

IUPAC Name

(2R)-2-amino-3-carbamoylpropanoic acid

Traditional Name

D-asparagine

CAS Registry Number

2058-58-4

SMILES

N[C@H](CC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1

InChI Key

DCXYFEDJOCDNAF-UWTATZPHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Asparagine and derivatives

Alternative Parents

Substituents

Asparagine or derivatives
Alpha-amino acid
D-alpha-amino acid
Fatty amide
Fatty acyl
Fatty acid
Carboxamide group
Amino acid
Primary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:28159 )
asparagine (CHEBI:28159 )
Other amino acids (C01905 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	168 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-4.3	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	2	ChemAxon
pKa (Strongest Basic)	8.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.41 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.35 m³·mol⁻¹	ChemAxon
Polarizability	11.77 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9100000000-5881591331bd059b7e7d	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9200000000-486021baa3768a16df83	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-015i-9700000000-74565d33539905a7f4e3	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-9100000000-439d8b494bcc2c657584	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3d057971482c08a22ae1	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-44107cc9e625603aa1d4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0016-9300000000-887eb70e6788b4b7c513	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d76a7af45b6c73471794	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-831feb8b7ce011d73c8e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0076-9200000000-1bed3281e3ab973b1841	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b990d7063181be79cb69	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-9300000000-e07b80cc3c9fd3b9281d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-5c032b7eeb69c0213827	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a7471da8aeb0443ffb99	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria

Biospecimen Locations

All Tissues
Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Placenta
Prostate
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018006	L-Asparagine	D-Asparagine	Broad specificity amino-acid racemase	Racemization	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Saliva	HMDB	23857558
Alzheimer's disease	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	17031479
Epilepsy		Association	Human Blood	HMDB	14992292
Frontotemporal dementia		Association	Human Saliva	HMDB	23857558
Fumarase deficiency		Association	Human Blood	HMDB	20549362
Fumarase deficiency	Slight Increase	Association	Human Urine	HMDB	20549362
Leukemia	Slight Decrease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	15911239
Schizophrenia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	7595563
Uremia		Association	Human Blood	HMDB	11865086
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis	Slight Increase	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Proteobacteria	2	Human ; Human feces
Bacteria	Firmicutes	1	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected and Quantified	1.68	2.90			uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.77	0.16			umol/mmol creatinine	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Blood	Detected and Quantified	36.5	17.2			uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Blood	Detected and Quantified	39.9	3.2			uM	Adult (>18 years old)	Both	Epilepsy	HMDB	14992292
Human Saliva	Detected and Quantified	0.97	1.12			uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Blood	Detected and Quantified	99				uM	Infant (0-1 year old)	Male	Fumaric aciduria	HMDB	20549362
Human Urine	Detected and Quantified			20.700	447	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Fumaric aciduria	HMDB	20549362
Human Blood	Detected and Quantified	31.3	11.3			uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Cerebrospinal fluid (csf)	Detected and Quantified	11.1	6.7			uM	Children (1-13 years old)	Not Specified	leukemia	HMDB	15911239
Human Cerebrospinal fluid (csf)	Detected and Quantified	7.9	6.4			uM	Children (1-13 years old)	Not Specified	Leukemia	HMDB	15911239
Human Saliva	Detected and Quantified	3.02	0.83			uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Blood	Detected and Quantified	25.6	10.3			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	31.89	13.6			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23535240
Human Blood	Detected and Quantified	32.4	13.7			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Blood	Detected and Quantified	34.5	14.5			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Cerebrospinal fluid (csf)	Detected and Quantified	6.01	0.65			uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	7595563
Human Blood	Detected and Quantified	40.8	11.5			uM	Children (1-13 years old)	Both	Uremia	HMDB	11865086
Human Urine	Detected and Quantified	8.75				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Urine	Detected and Quantified	<3.0				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	3168222
Human Urine	Detected and Quantified	<4.0				umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	HMDB	3168222
Human Urine	Detected and Quantified	<5.0				umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	3168222
Human Urine	Detected and Quantified			0.42	10.5	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.96	0.65			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Saliva	Detected and Quantified	1.76	2.11			uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Urine	Detected and Quantified	10.0		4.6	16.32	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18004736
Human Urine	Detected and Quantified	10.1		4.6	17.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	10.52	3.85			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15992788
Human Breast milk	Detected and Quantified	16.6	10.5			uM	Adult (>18 years old)	Female	Normal	HMDB	24027187
Human Cerebrospinal fluid (csf)	Detected and Quantified	19.0	11.1			uM	Children (1-13 years old)	Not Specified	Normal	HMDB	15911239
Human Urine	Detected and Quantified			2.1	5.5	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			2.5	3.7	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	2.68		0.36	10.57	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	2.81		1.84	5.77	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Blood	Detected and Quantified			29	132	uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	20549362
Human Feces	Detected and Quantified	30	30			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	32.9	7.6			uM	Adult (>18 years old)	Both	Normal	HMDB	11865086
Human Blood	Detected and Quantified	35.0		16.4	57.2	uM	Adult (>18 years old)	Both	Normal	HMDB	18004736
Human Urine	Detected and Quantified			4.296	155.231	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	20549362
Human Cerebrospinal fluid (csf)	Detected and Quantified	4.43		0.0	8.86	uM	Adult (>18 years old)	Both	Normal	HMDB	18502700
Human Urine	Detected and Quantified			4.66	16.53	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18004736
Human Blood	Detected and Quantified	41.0		31.0	51.0	uM	Adult (>18 years old)	Both	Normal	HMDB	12297216
Human Blood	Detected and Quantified	48.4	9.29			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Cerebrospinal fluid (csf)	Detected and Quantified	5.99	0.92			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	7595563
Human Blood	Detected and Quantified	54.4		47.3	68.3	uM	Children (1-13 uears old)	Both	Normal	HMDB	27294788
Human Cerebrospinal fluid (csf)	Detected and Quantified	6.20		5.90	6.50	uM	Adult (>18 years old)	Both	Normal	HMDB	14992292
Human Blood	Detected and Quantified	61.7	12.09			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Cerebrospinal fluid (csf)	Detected and Quantified	8.1	4.9			uM	Adult (>18 years old)	Male	Normal	HMDB	6198473
Human Urine	Detected and Quantified	8.8		4.6	17.7	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	82.4	7.3			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Cerebrospinal fluid (csf)	Detected and Quantified	9.0	4.2			uM	Adult (>18 years old)	Female	Normal	HMDB	6198473
Human Urine	Detected and Quantified	9.5		3.0	26.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	29.6797	15.0964			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	35.098	22.947			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	25.158	23.462			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	35.7098	12.6254			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Cerebrospinal fluid (csf)	Detected and Quantified			4	10	uM	Children (0 - 10 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Cerebrospinal fluid (csf)	Detected and Quantified			4	10	uM	Adolescent (>11 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	19.56	umol/mmol creatinine	Adolescent (13 - 21 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	19.56	umol/mmol creatinine	Adult (>21 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	25.33	umol/mmol creatinine	Children (4 - 13 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	26.23	umol/mmol creatinine	Children (2 - 4 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	28.15	umol/mmol creatinine	Children (1 - 2 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	32.00	umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	53.03	umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	77.90	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified			23	79	uM	Children (3 months - 6 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified			25	75	uM	Children (6 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified			33	77	uM	Infant (1 - 3 months old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified			36	87	uM	Newborn (0-30 days old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			15.15	53.01	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Blood	Detected and Quantified	46.0	7.0			uM	Children (1-13 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	47.0	9.0			uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	48.0	7.0			uM	Children (1-13 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	49.0	7.0			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Cerebrospinal fluid (csf)	Detected and Quantified	5.4	1.4			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.580	0.511			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.20	0.809			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.24	0.768			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.70	1.69			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.74	0.972			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	2.17	1.41			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Blood	Detected and Quantified			29.0	90.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Urine	Detected and Quantified			2.49	32.012	umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			2.83	113.12	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			2.83	26.92	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			3.17	46.60	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			4.30	44.79	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			7.013	100.00	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human All tissues	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0033780

DrugBank ID

DB03943

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011935

KNApSAcK ID

Not Available

Chemspider ID

388679

KEGG Compound ID

C01905

BioCyc ID

CPD-3633

BiGG ID

Not Available

Wikipedia Link

Asparagine

METLIN ID

Not Available

PubChem Compound

439600

PDB ID

DSG

ChEBI ID

28159

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. doi: 10.1111/j.1471-4159.1984.tb02756.x. [PubMed:6198473 ]
Ahlman B, Andersson K, Leijonmarck CE, Ljungqvist O, Hedenborg L, Wernerman J: Short-term starvation alters the free amino acid content of the human intestinal mucosa. Clin Sci (Lond). 1994 Jun;86(6):653-62. doi: 10.1042/cs0860653. [PubMed:7914846 ]
Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. doi: 10.1016/s0899-9007(02)00780-3. [PubMed:12297216 ]
Fischer D, Schroers A, Blumcke I, Urbach H, Zerres K, Mortier W, Vorgerd M, Schroder R: Consequences of a novel caveolin-3 mutation in a large German family. Ann Neurol. 2003 Feb;53(2):233-41. doi: 10.1002/ana.10442. [PubMed:12557291 ]
Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. doi: 10.1023/b:nere.0000010461.34920.0c. [PubMed:14992292 ]
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Chiara F, Goumans MJ, Forsberg H, Ahgren A, Rasola A, Aspenstrom P, Wernstedt C, Hellberg C, Heldin CH, Heuchel R: A gain of function mutation in the activation loop of platelet-derived growth factor beta-receptor deregulates its kinase activity. J Biol Chem. 2004 Oct 8;279(41):42516-27. doi: 10.1074/jbc.M406051200. Epub 2004 Jul 28. [PubMed:15284236 ]
Avramis VI, Panosyan EH: Pharmacokinetic/pharmacodynamic relationships of asparaginase formulations: the past, the present and recommendations for the future. Clin Pharmacokinet. 2005;44(4):367-93. doi: 10.2165/00003088-200544040-00003. [PubMed:15828851 ]
Takamatsu S, Inoue N, Katsumata T, Nakamura K, Fujibayashi Y, Takeuchi M: The relationship between the branch-forming glycosyltransferases and cell surface sugar chain structures. Biochemistry. 2005 Apr 26;44(16):6343-9. doi: 10.1021/bi047606a. [PubMed:15835923 ]
Poon CJ, Plaas AH, Keene DR, McQuillan DJ, Last K, Fosang AJ: N-linked keratan sulfate in the aggrecan interglobular domain potentiates aggrecanase activity. J Biol Chem. 2005 Jun 24;280(25):23615-21. doi: 10.1074/jbc.M412145200. Epub 2005 Apr 22. [PubMed:15849197 ]
Mohrmann K, van Eijndhoven MA, Schinkel AH, Schellens JH: Absence of N-linked glycosylation does not affect plasma membrane localization of breast cancer resistance protein (BCRP/ABCG2). Cancer Chemother Pharmacol. 2005 Oct;56(4):344-50. doi: 10.1007/s00280-005-1004-5. Epub 2005 May 5. [PubMed:15875186 ]
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Showing metabocard for D-Asparagine (MMDBc0033158)

MOL for #<Metabolite:0x00007fa5083ec1f0>

3D MOL for #<Metabolite:0x00007fa5083ec1f0>

3D SDF for #<Metabolite:0x00007fa5083ec1f0>

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Structure for #<Metabolite:0x00007fa5083ec1f0>

3D Structure for #<Metabolite:0x00007fa5083ec1f0>