MiMeDB: Showing metabocard for Citric acid (MMDBc0000024)

Read more...Show more...

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:27:35 UTC

Update Date

2024-09-27 18:35:51 UTC

Metabolite ID

MMDBc0000024

Metabolite Identification

Common Name

Citric acid

Description

Citric acid (citrate) is a weak acid that is formed in the tricarboxylic acid cycle or that may be introduced with diet. The evaluation of plasma citric acid is scarcely used in the diagnosis of human diseases. On the contrary urinary citrate excretion is a common tool in the differential diagnosis of kidney stones, renal tubular acidosis and it plays also a role in bone diseases. The importance of hypocitraturia should be considered with regard to bone mass, urine crystallization and urolithiasis. (PMID 12957820 ) The secretory epithelial cells of the prostate gland of humans and other animals posses a unique citrate-related metabolic pathway regulated by testosterone and prolactin. This specialized hormone-regulated metabolic activity is responsible for the major prostate function of the production and secretion of extraordinarily high levels of citrate. The key regulatory enzymes directly associated with citrate production in the prostate cells are mitochondrial aspartate aminotransferase, pyruvate dehydrogenase, and mitochondrial aconitase. testosterone and prolactin are involved in the regulation of the corresponding genes associated with these enzymes. The regulatory regions of these genes contain the necessary response elements that confer the ability of both hormones to control gene transcription. Protein kinase C (PKC) is the signaling pathway for the prolactin regulation of the metabolic genes in prostate cells. testosterone and prolactin regulation of these metabolic genes (which are constitutively expressed in all mammalian cells is specific for these citrate-producing cells (PMID 12198595 ). Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Little information is available as the condition appears to be rare, but like other types of food intolerance it is often described as a "pseudo-allergic" reaction. Moreover, citric acid is found to be associated with maple syrup urine disease, primary hypomagnesemia, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism.

Structure

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

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    3   12                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   11    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8                                                            
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   12                                                       
CONECT   11    4   12                                                       
CONECT   12   10   11    1   13                                             
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
2-Hydroxy-1,2,3-propanetricarboxylic acid	ChEBI
2-Hydroxytricarballylic acid	ChEBI
3-Carboxy-3-hydroxypentane-1,5-dioic acid	ChEBI
Citronensaeure	ChEBI
e330	ChEBI
H3Cit	ChEBI
Anhydrous citric acid	Kegg
Citric acid anhydrous	Kegg
2-Hydroxy-1,2,3-propanetricarboxylate	Generator
2-Hydroxytricarballylate	Generator
3-Carboxy-3-hydroxypentane-1,5-dioate	Generator
Anhydrous citrate	Generator
Citrate anhydrous	Generator
Citrate	Generator
Aciletten	HMDB
beta-Hydroxytricarballylate	HMDB
beta-Hydroxytricarballylic acid	HMDB
Chemfill	HMDB
Citraclean	HMDB
Citretten	HMDB
Citro	HMDB
e 330	HMDB
Hydrocerol a	HMDB
Kyselina citronova	HMDB
Suby g	HMDB
Uro-trainer	HMDB
Acid monohydrate, citric	HMDB
Monohydrate, citric acid	HMDB
Citric acid, anhydrous	HMDB
Citric acid monohydrate	HMDB
Uralyt u	HMDB

Molecular Formula

C₆H₈O₇

Average Mass

192.1235

Monoisotopic Mass

192.02700261

IUPAC Name

2-hydroxypropane-1,2,3-tricarboxylic acid

Traditional Name

citric acid

CAS Registry Number

77-92-9

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChI Key

KRKNYBCHXYNGOX-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0002-0941000000-c310fda0e6a19bf6ae40	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0002-0941000000-f1dfda3e9abc7cfb6b2a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-006t-0952000000-ba3a1a80815f65afd05c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0951000000-48857e9baebe16d9fc8d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00di-9531000000-b6fd7d038634694f0873	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-00di-0593000000-b193bbba8c0cefdfe42a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0941000000-c310fda0e6a19bf6ae40	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0941000000-f1dfda3e9abc7cfb6b2a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-0952000000-ba3a1a80815f65afd05c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0951000000-48857e9baebe16d9fc8d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9531000000-b6fd7d038634694f0873	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-0593000000-b193bbba8c0cefdfe42a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0941000000-573230e47a4efb1e36a5	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002k-6900000000-d1a61a52f6efdec3101a	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-02ib-6019300000-6d5ebea10441c6d4149a	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03di-2900000000-956001b034bbc0b7da96	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000l-9100000000-55e34e2c1616942fd4f2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000f-9000000000-7b8be3e90a4daf85f04a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0911200000-af80d22f720facc4813a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-6f4fedbb19821898fb22	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-8eff68ab89f7ce2262be	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0fsi-0019300000-b370c4c3dd656c8eb729	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0912100000-05e8ceb6dd97f7b9af98	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-e4b67745443c48a63bd6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-92536abec982e0a653a0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-35772df08490f451d828	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-35856cc258368d13e1ff	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-3900000000-7170fdcb9749e6d6c2fb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-01p9-9500000000-9a502981b0a9e1ea35ad	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000i-9100000000-ed0c86b90e1f4966d025	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4r-9000000000-b8a975c2d639d8c91afb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-2900000000-30970a4250098e148658	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-a587dddf188152c5d7b0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-3900000000-7170fdcb9749e6d6c2fb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01p9-9500000000-9a502981b0a9e1ea35ad	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9100000000-42a125e9128ce21bd785	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9000000000-b8a975c2d639d8c91afb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-03di-0900000000-32af4c1bf55ea1563e53	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-9000000000-6f4fedbb19821898fb22	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-8eff68ab89f7ce2262be	2017-09-14	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9400000000-fb757b614278bb898b54	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)		2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	403	Human ; Human sputum; Human subgingival plaque; Human feces; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Human supragingival plaque	Microbial culture; Metabolic reconstruction
Bacteria	Firmicutes	482	Human ; Human saliva; Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human subgingival plaque; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Deinococcus-thermus	5		Microbial culture
Bacteria	Bacteroidetes	139	Human feces; Human stool; Human urine; Human appendix biopsy; Human ; Human saliva; Human gastric fluid; Human supragingival plaque; Human subgingival plaque	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	176	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Microbial culture; Metabolic reconstruction
Bacteria	Chloroflexi	2		Microbial culture
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	6	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	32	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	3	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	nah	2
Eukaryota/Fungi	Ascomycota	17	Human feces; Human saliva	Unknown
Archaea/Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria	Aquificae	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified			149.400	152.400	uM	Children (1-13 years old)	Both	2-Ketoglutarate dehydrogenase complex deficiency	HMDB	7075624
Human Blood	Detected and Quantified			71	107	uM	Children (1-13 years old)	Both	2-Ketoglutarate dehydrogenase complex deficiency	HMDB	7075624
Human Saliva	Detected and Quantified	66.67	68.53			uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Urine	Detected and Quantified			1.177	354.851	umol/mmol creatinine	Infant (0-1 year old)	Both	Amish lethal microcephaly	HMDB	12376931
Human Urine	Detected and Quantified	80.9	1.8			umol/mmol creatinine	Adult (>18 years old)	Both	Argininosuccinic aciduria (ASL)	HMDB	19551947
Human Cerebrospinal fluid (csf)	Detected and Quantified	2400				uM	Adult (>18 years old)	Both	Canavan Disease	HMDB	7729054
Human Urine	Detected and Quantified	998				umol/mmol creatinine	Newborn (0-30 days old)	Female	Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome	HMDB	17994565
Human Blood	Detected and Quantified	85.9	19.1			uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Saliva	Detected and Quantified	67.38	26.37			uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Blood	Detected and Quantified	117.6	37.2			uM	Adult (>18 years old)	Both	Hyperoxalemia	HMDB	15353324
Human Blood	Detected and Quantified	141.3	54.7			uM	Adult (>18 years old)	Both	Hyperoxalemia	HMDB	15353324
Human Blood	Detected and Quantified	85.9	26.9			uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Saliva	Detected and Quantified	85.33	8.98			uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Urine	Detected and Quantified	268.0		53.0	1111.0	umol/mmol creatinine	Not Specified	Both	Lung cancer	HMDB	18953024
Human Urine	Detected and Quantified	576.1	15.2			umol/mmol creatinine	Adult (>18 years old)	Both	Maple syrup urine disease	HMDB	19551947
Human Urine	Detected and Quantified	11.2				umol/mmol creatinine	Adult (>18 years old)	Both	Paraquat poisoning	HMDB	9625050
Human Urine	Detected and Quantified	291.9	14.6			umol/mmol creatinine	Adult (>18 years old)	Both	Phenylketonuria	HMDB	19551947
Human Urine	Detected and Quantified	81.8	10.4			umol/mmol creatinine	Adult (>18 years old)	Both	Phenylketonuria	HMDB	19551947
Human Blood	Detected and Quantified	51.9	16.5			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	61.85	13.38			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Blood	Detected and Quantified	66.1	22.9			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23535240
Human Blood	Detected and Quantified	74.1	23.5			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Blood	Detected and Quantified	79.3	19.3			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Urine	Detected and Quantified	17.35				umol/mmol creatinine	Children (1-13 years old)	Female	Primary Hypomagnesemia	HMDB	12720080
Human Urine	Detected and Quantified	689.6	47.3			umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	HMDB	19551947
Human Urine	Detected and Quantified	712.3	82.8			umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	HMDB	19551947
Human Urine	Detected and Quantified	154				umol/mmol creatinine	Adult (>18 years old)	Female	Rhabdomyolysis	HMDB	12089184
Human Urine	Detected and Quantified	457.6	17.5			umol/mmol creatinine	Adult (>18 years old)	Both	Tyrosinemia I	HMDB	19551947
Human Urine	Detected and Quantified	300				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9625050
Human Urine	Detected and Quantified	440				umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	25155776
Human Urine	Detected and Quantified	440.6				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21388201
Human Urine	Detected and Quantified			0	21.0	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	22.7	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	33.7	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	4.1	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Saliva	Detected and Quantified			1	4456	uM	Adult (>18 years old)	Male	normal	HMDB	19259987
Human Blood	Detected and Quantified	114.2	27			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	122.3	27.85			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Urine	Detected and Quantified			135	271	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			137	210	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			14.712	73.559	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	12376931
Human Urine	Detected and Quantified	155		70	226	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected and Quantified	172.8	87.4			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	17474139
Human Saliva	Detected and Quantified	18		1	338	uM	Adult (>18 years old)	Male	Normal	HMDB	19259987
Human Urine	Detected and Quantified	184.2		58.7	651.7	umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human Blood	Detected and Quantified	190.0		30.0	400.0	uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Saliva	Detected and Quantified	192		10	1857	uM	Adult (>18 years old)	Male	Normal	HMDB	19259987
Human Urine	Detected and Quantified	203		49	600	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	208.6		33.2	445.1	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Cerebrospinal fluid (csf)	Detected and Quantified	225	96			uM	Adult (>18 years old)	Both	Normal	HMDB	18502700
Human Urine	Detected and Quantified	226.32	98.12			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Breast milk	Detected and Quantified	2700	680			uM	Adult (>18 years old)	Female	Normal	HMDB	24027187
Human Urine	Detected and Quantified	271.8	90.0			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15992788
Human Urine	Detected and Quantified	280.6	115.2			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	17474139
Human Blood	Detected and Quantified			30.00	400.0	uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Saliva	Detected and Quantified	320		15	4984	uM	Adult (>18 years old)	Female	Normal	HMDB	19259987
Human Cerebrospinal fluid (csf)	Detected and Quantified	350.0	240.0			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	8412012
Human Saliva	Detected and Quantified	370		3	66177	uM	Adult (>18 years old)	Male	Normal	HMDB	19259987
Human Cerebrospinal fluid (csf)	Detected and Quantified	370.0		110.0	630.0	uM	Adult (>18 years old)	Both	Normal	HMDB	7729054
Human Urine	Detected and Quantified	371		102	611	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	6321058
Human Urine	Detected and Quantified	382.2	208.3			umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified			39.6	893.5	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Blood	Detected and Quantified			40	160	uM	Not Specified	Not Specified	Normal	HMDB	7075624
Human Cerebrospinal fluid (csf)	Detected and Quantified	400.0	170.0			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	1931558
Human Urine	Detected and Quantified	422.9	246.8			umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified			46	1400	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Blood	Detected and Quantified	54.2	0.8			uM	Children (1-13 years old)	Both	Normal	HMDB	9573551
Human Urine	Detected and Quantified	708.9		25.2	3168.4	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Cerebrospinal fluid (csf)	Detected and Quantified			75	275	uM	Not Specified	Not Specified	Normal	HMDB	7075624
Human Saliva	Detected and Quantified	83.90	37.92			uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Urine	Detected and Quantified	972.5		89.5	1647.7	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	478.296	354.079			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	304.51	105.96 ‚Äì 586.60			umol/mmol creatinine	Adult (>18 years old)	Both	Type 1 diabetes Mellitus	HMDB	Lorena Ivona ŞTEFAN, Alina NICOLESCU, Simona POPA, Maria MOŢA, Eugenia KOVACS and Calin DELEANU. 1H-NMR URINE METABOLIC PROFILING IN TYPE 1 DIABETES MELLITUS. Rev. Roum. Chim., 2010, 55(11-12), 1033-1037
Human Urine	Detected and Quantified	493.679	202.522			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	<757.09				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			46.87	484.31	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	122.0	30.0			uM	Children (1-13 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 Cerebrospinal fluid (csf)	Detected and Quantified	176.0	50.0			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 Urine	Detected and Quantified	181.0	97.0			umol/mmol creatinine	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 Urine	Detected and Quantified	242.0	129.6			umol/mmol creatinine	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	88.0	33.0			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 Urine	Detected and Quantified	242.34	81.79 ‚Äì 403.84			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Lorena Ivona ŞTEFAN, Alina NICOLESCU, Simona POPA, Maria MOŢA, Eugenia KOVACS and Calin DELEANU. 1H-NMR URINE METABOLIC PROFILING IN TYPE 1 DIABETES MELLITUS. Rev. Roum. Chim., 2010, 55(11-12), 1033-1037
Human Urine	Detected and Quantified	119.45				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Human Saliva	Detected and Quantified	10.9	8.35			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	12.2	7.87			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	16.9	9.95			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	18.1	10.3			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	28.50	9.89			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
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
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	16939360
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	16939360
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	12097436
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22148915
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22024767
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22007635
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22800120
Human Sweat	Detected but not Quantified						Adult	Both	Normal	HMDB	26755145
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	28842642
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

References

General References

Moreno AJ, Brown JM, Salinas JA, Feaster BL 3rd, Brown TJ: Ga-67 positivity in sarcoidosis of the skin with coincident thyroid uptake of uncertain etiology. Clin Nucl Med. 1984 Mar;9(3):165-6. doi: 10.1097/00003072-198403000-00015. [PubMed:6705419 ]
Wenk J, Foitzik A, Achterberg V, Sabiwalsky A, Dissemond J, Meewes C, Reitz A, Brenneisen P, Wlaschek M, Meyer-Ingold W, Scharffetter-Kochanek K: Selective pick-up of increased iron by deferoxamine-coupled cellulose abrogates the iron-driven induction of matrix-degrading metalloproteinase 1 and lipid peroxidation in human dermal fibroblasts in vitro: a new dressing concept. J Invest Dermatol. 2001 Jun;116(6):833-9. doi: 10.1046/j.1523-1747.2001.01345.x. [PubMed:11407968 ]
Wei R, Han JJ, Bai B, Ren DL, Chen B, Yang MF, Xia ZL: Analysis of factors influencing the blood levels and activities of tissue-type plasminogen activator (t-PA). Clin Hemorheol Microcirc. 2003;29(3-4):351-6. [PubMed:14724361 ]
McBane RD 2nd, Karnicki K, Tahirkheli N, Miller RS, Owen WG: Platelet characteristics associated with coronary artery disease. J Thromb Haemost. 2003 Jun;1(6):1296-303. doi: 10.1046/j.1538-7836.2003.00183.x. [PubMed:12871333 ]
Jurasovic J, Cvitkovic P, Pizent A, Colak B, Telisman S: Semen quality and reproductive endocrine function with regard to blood cadmium in Croatian male subjects. Biometals. 2004 Dec;17(6):735-43. doi: 10.1007/s10534-004-1689-7. [PubMed:15689116 ]
Mairiang E, Hanpanich P, Sriboonlue P: In vivo 31P-MRS assessment of muscle-pH, cytolsolic-[Mg2+] and phosphorylation potential after supplementing hypokaliuric renal stone patients with potassium and magnesium salts. Magn Reson Imaging. 2004 Jun;22(5):715-9. doi: 10.1016/j.mri.2004.01.038. [PubMed:15172066 ]
Tammen H, Schulte I, Hess R, Menzel C, Kellmann M, Mohring T, Schulz-Knappe P: Peptidomic analysis of human blood specimens: comparison between plasma specimens and serum by differential peptide display. Proteomics. 2005 Aug;5(13):3414-22. doi: 10.1002/pmic.200401219. [PubMed:16038021 ]
Chiueh CC, Andoh T, Lai AR, Lai E, Krishna G: Neuroprotective strategies in Parkinson's disease: protection against progressive nigral damage induced by free radicals. Neurotox Res. 2000;2(2-3):293-310. doi: 10.1007/BF03033799. [PubMed:16787846 ]
Batchelor WB, Tolleson TR, Huang Y, Larsen RL, Mantell RM, Dillard P, Davidian M, Zhang D, Cantor WJ, Sketch MH Jr, Ohman EM, Zidar JP, Gretler D, DiBattiste PM, Tcheng JE, Califf RM, Harrington RA: Randomized COMparison of platelet inhibition with abciximab, tiRofiban and eptifibatide during percutaneous coronary intervention in acute coronary syndromes: the COMPARE trial. Comparison Of Measurements of Platelet aggregation with Aggrastat, Reopro, and Eptifibatide. Circulation. 2002 Sep 17;106(12):1470-6. doi: 10.1161/01.cir.0000029744.01096.1f. [PubMed:12234950 ]
A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. doi: 10.1021/ac051211v. [PubMed:16351159 ]
Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [PubMed:9625050 ]
Wan KW, Malgesini B, Verpilio I, Ferruti P, Griffiths PC, Paul A, Hann AC, Duncan R: Poly(amidoamine) salt form: effect on pH-dependent membrane activity and polymer conformation in solution. Biomacromolecules. 2004 May-Jun;5(3):1102-9. doi: 10.1021/bm040007z. [PubMed:15132705 ]
Solheim BG, Flesland O, Brosstad F, Mollnes TE, Seghatchian J: Improved preservation of coagulation factors after pre-storage leukocyte depletion of whole blood. Transfus Apher Sci. 2003 Oct;29(2):133-9. doi: 10.1016/S1473-0502(03)00117-4. [PubMed:12941351 ]
Seiffert D, Thomas BE, Bradley JD, Munzer DA, Tchinnes MA, Kornhauser DM, Cain VA, Hua TA, Feuerstein GZ, Martin DE, Stern AM: Effects of the glycoprotein IIb/IIIa antagonist Roxifiban on P-selectin expression, fibrinogen binding, and microaggregate formation in a phase I dose-finding study: no evidence for platelet activation during treatment with a glycoprotein IIb/IIIa antagonist. Platelets. 2003 May;14(3):179-87. doi: 10.1080/0953710031000092820. [PubMed:12850842 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. doi: 10.1007/BF00711898. [PubMed:8412012 ]
Odvina CV, Mason RP, Pak CY: Prevention of thiazide-induced hypokalemia without magnesium depletion by potassium-magnesium-citrate. Am J Ther. 2006 Mar-Apr;13(2):101-8. doi: 10.1097/01.mjt.0000149922.16098.c0. [PubMed:16645424 ]
Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. [PubMed:7729054 ]
Commodari F, Arnold DL, Sanctuary BC, Shoubridge EA: 1H NMR characterization of normal human cerebrospinal fluid and the detection of methylmalonic acid in a vitamin B12 deficient patient. NMR Biomed. 1991 Aug;4(4):192-200. doi: 10.1002/nbm.1940040407. [PubMed:1931558 ]
McBane RD 2nd, Karnicki K, Miller RS, Owen WG: The impact of peripheral arterial disease on circulating platelets. Thromb Res. 2004;113(2):137-45. doi: 10.1016/j.thromres.2004.02.007. [PubMed:15115669 ]
Abe T, Kobata H, Hanba Y, Kitabata Y, Narukawa N, Hasegawa H, Abe T, Fukagawa M: Study of plasma exchange for liver failure: beneficial and harmful effects. Ther Apher Dial. 2004 Jun;8(3):180-4. doi: 10.1111/j.1526-0968.2004.00149.x. [PubMed:15154867 ]
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:19212411 ]
Caudarella R, Vescini F, Buffa A, Stefoni S: Citrate and mineral metabolism: kidney stones and bone disease. Front Biosci. 2003 Sep 1;8:s1084-106. doi: 10.2741/1119. [PubMed:12957820 ]
Costello LC, Franklin RB: Testosterone and prolactin regulation of metabolic genes and citrate metabolism of prostate epithelial cells. Horm Metab Res. 2002 Aug;34(8):417-24. doi: 10.1055/s-2002-33598. [PubMed:12198595 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Hu YY, Rawal A, Schmidt-Rohr K: Strongly bound citrate stabilizes the apatite nanocrystals in bone. Proc Natl Acad Sci U S A. 2010 Dec 28;107(52):22425-9. doi: 10.1073/pnas.1009219107. Epub 2010 Dec 2. [PubMed:21127269 ]

Showing metabocard for Citric acid (MMDBc0000024)

MOL for #<Metabolite:0x00007f53b9539350>

3D MOL for #<Metabolite:0x00007f53b9539350>

3D SDF for #<Metabolite:0x00007f53b9539350>

3D-SDF for #<Metabolite:0x00007f53b9539350>

PDB for #<Metabolite:0x00007f53b9539350>

3D PDB for #<Metabolite:0x00007f53b9539350>

SMILES for #<Metabolite:0x00007f53b9539350>

INCHI for #<Metabolite:0x00007f53b9539350>

Structure for #<Metabolite:0x00007f53b9539350>

3D Structure for #<Metabolite:0x00007f53b9539350>