| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:03 -0700 |
| HMDB ID |
HMDB00193 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Isocitric acid |
| Description |
The citrate oxidation to isocitrate is catalyzed by the enzyme aconitase. Human prostatic secretion is remarkably rich in citric acid and low aconitase activity will therefore play a significant role in enabling accumulation of high citrate levels (PubMed ID 8115279). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-Hydroxy-1,2,3-propanetricarboxylate
- 1-Hydroxy-1,2,3-propanetricarboxylic acid
- 1-Hydroxypropane-1,2,3-tricarboxylate
- 1-Hydroxypropane-1,2,3-tricarboxylic acid
- 1-Hydroxytricarballylate
- 1-Hydroxytricarballylic acid
- 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate
- 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid
- 3-Carboxy-2,3-dideoxy-Pentarate
- 3-Carboxy-2,3-dideoxy-Pentaric acid
- D-Isocitrate
- I-CIT
- Isocitrate
- Threo-D(S)-iso-citrate
- Threo-Ds-isocitrate
|
| Chemical Formula |
C6H8O7 |
| Average Molecular Weight |
192.1235 |
| Monoisotopic Molecular Weight |
192.02700261 |
| IUPAC Name |
1-hydroxypropane-1,2,3-tricarboxylic acid |
| Traditional IUPAC Name |
isocitric acid |
| CAS Registry Number |
320-77-4 |
| SMILES |
OC(C(CC(O)=O)C(O)=O)C(O)=O |
| InChI Identifier |
InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13) |
| InChI Key |
ODBLHEXUDAPZAU-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Organic Acids and Derivatives |
| Class |
Carboxylic Acids and Derivatives |
| Sub Class |
Tricarboxylic Acids and Derivatives |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- Branched Fatty Acids
- Organic Compounds
- isocitric acid(ChEBI)
|
| Substituents |
- Alpha Hydroxy Acid
- Beta Hydroxy Acid
- Carboxylic Acid
- Secondary Alcohol
- Short Chain Hydroxy Acid
- Succinic Acid
|
| Direct Parent |
Tricarboxylic Acids and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Glutathione metabolism
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Mitochondria
- Peroxisome
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
162 - 165 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
466 mg/mL |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|
| Gas-MS Spectrum |
| 1H NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 |
| [1H,13C] 2D NMR Spectrum |
|
| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Mitochondria
- Peroxisome
|
| Biofluid Locations |
- Blood
- Cellular Cytoplasm
- Cerebrospinal Fluid (CSF)
- Semen
- Urine
|
| Tissue Location |
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
6.0 (0.0-10.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cellular Cytoplasm |
Detected and Quantified |
|
38 (23-53) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
10.0 +/- 9.0 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Semen |
Detected and Quantified |
|
400 - 1500 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
56.8(19.4-119.1) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by GC-MS
|
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Urine compound detected by GC-MS
|
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
94.3 (29.8-154.4) umol/mmol creatinine |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
120.1 (101.1-265.3) umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
53.7 (31.9-83.1) umol/mmol creatinine |
Children (1-13 year old) |
Both |
Normal |
2-6 years
|
| Urine |
Detected and Quantified |
|
45.0 (18.0-69.9) umol/mmol creatinine |
Children (1-13 year old) |
Both |
Normal |
6-10 years
|
| Urine |
Detected and Quantified |
|
38.9 (16.0-118.0) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
19.0 (5.0-34.0) umol/mmol creatinine |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
7.7 (5.0-12.0) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
24.52 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Based on one measurement
|
| Urine |
Detected and Quantified |
|
58 (36-84) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
46.9 (20.4-89.2) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and Quantified |
|
19.08 (5.26 - 42.76) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
22.0 +/- 13.8 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
14.7 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Cellular Cytoplasm |
Detected and Quantified |
|
15 (14.8-15.2) uM |
Adult (>18 years old) |
Both |
Anoxia |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Autosomal dominant polycystic kidney disease |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Anoxia |
- Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36.
Pubmed: 8579834
|
|
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB003281 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
1161  |
| KEGG Compound ID |
C00311  |
| BioCyc ID |
threo-d(s)-iso-citrate  |
| BiGG ID |
34579  |
| Wikipedia Link |
Isocitric acid  |
| NuGOwiki Link |
HMDB00193  |
| Metagene Link |
HMDB00193  |
| METLIN ID |
3328  |
| PubChem Compound |
1198  |
| PDB ID |
1B0J  |
| ChEBI ID |
30887  |
| References |
| Synthesis Reference |
Finogenova, T. V.; Kamzolova, S. V.; Dedyukhina, E. G.; Shishkanova, N. V.; Il'chenko, A. P.; Morgunov, I. G.; Chernyavskaya, O. G.; Sokolov, A. P. Biosynthesis of citric and isocitric acids from ethanol by mutant Yarrowia lipolytica N 1 under continuous cultivation. Applied Microbiology and Biotechnology (2002), 59(4-5), 493-500. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6.
Pubmed: 813176
- Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36.
Pubmed: 8579834
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.
Pubmed: 8087979
- Sutor DJ, Percival JM, Doonan S: Isolation and identification of some urinary inhibitors of calcium phosphate formation. Clin Chim Acta. 1978 Oct 16;89(2):273-8.
Pubmed: 213213
- Ebeling K, Ruckhaberle KE, Bilek K: [Studies on the recording of cytostatic effects on organ cultures of squamous cell carcinoma of the uterine cervix] Zentralbl Gynakol. 1977;99(20):1249-59.
Pubmed: 595962
- Sutor DJ, Percival JM, Doonan S: Urinary inhibitor of the formation of calcium oxalate. Br J Urol. 1979 Aug;51(4):253-5.
Pubmed: 223711
- Hennequin C, Lalanne V, Daudon M, Lacour B, Drueke T: A new approach to studying inhibitors of calcium oxalate crystal growth. Urol Res. 1993 Mar;21(2):101-8.
Pubmed: 8389069
- Kavanagh JP: Isocitric and citric acid in human prostatic and seminal fluid: implications for prostatic metabolism and secretion. Prostate. 1994;24(3):139-42.
Pubmed: 8115279
- Mikosha AS, Monissarenko VP, Bychkovskaia LA: [Properties of adrenocortical isocitrate dehydrogenase] Vopr Med Khim. 1981 Nov-Dec;27(6):736-9.
Pubmed: 7336646
- 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.
Pubmed: 8412012
- Sutor DJ, Percival JM: The estimation of D-isocitric acid in urine using isocitrate dehydrogenase. Clin Chim Acta. 1978 Jun;86(2):223-5.
Pubmed: 657545
|