Ureidosuccinic acid (BioDeep_00000003364)
Secondary id: BioDeep_00000400471, BioDeep_00000593355, BioDeep_00001868335
natural product human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
化学式: C5H8N2O5 (176.0433198)
中文名称: 脲基琥珀酸, N-氨基甲酰基-DL-天冬氨酸
谱图信息:
最多检出来源 Viridiplantae(plant) 0.5%
分子结构信息
SMILES: C(C(C(=O)O)NC(=O)N)C(=O)O
InChI: InChI=1S/C5H8N2O5/c6-5(12)7-2(4(10)11)1-3(8)9/h2H,1H2,(H,8,9)(H,10,11)(H3,6,7,12)
描述信息
N-carbamoyl-l-aspartate, also known as N-carbamoylaspartic acid or L-ureidosuccinic acid, belongs to aspartic acid and derivatives class of compounds. Those are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-carbamoyl-l-aspartate is soluble (in water) and a weakly acidic compound (based on its pKa). N-carbamoyl-l-aspartate can be found in a number of food items such as mustard spinach, black huckleberry, towel gourd, and chinese cabbage, which makes N-carbamoyl-l-aspartate a potential biomarker for the consumption of these food products. N-carbamoyl-l-aspartate can be found primarily in prostate Tissue and saliva, as well as in human prostate tissue. In humans, N-carbamoyl-l-aspartate is involved in a couple of metabolic pathways, which include aspartate metabolism and pyrimidine metabolism. N-carbamoyl-l-aspartate is also involved in several metabolic disorders, some of which include beta ureidopropionase deficiency, dihydropyrimidinase deficiency, canavan disease, and UMP synthase deficiency (orotic aciduria). Moreover, N-carbamoyl-l-aspartate is found to be associated with prostate cancer.
Ureidosuccinic acid, also known as L-ureidosuccinate or carbamyl-L-aspartate, belongs to the class of organic compounds known as aspartic acids and derivatives. Aspartic acids and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Ureidosuccinic acid is also classified as a carbamate derivative. It is a solid that is soluble in water. Ureidosuccinic acid exists in all living species, ranging from bacteria to plants to humans. Ureidosuccinic acid can be biosynthesized from carbamoyl phosphate and L-aspartic acid through the action of the enzyme known as aspartate carbamoyltransferase (ACTase) and serves as an intermediate in pyrimidine biosynthesis. In humans, a drop in the level of urinary ureidosuccinic acid is associated with bladder cancer (PMID: 25562196). It is also involved in the metabolic disorder called Canavan disease.
Acquisition and generation of the data is financially supported in part by CREST/JST.
D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids
KEIO_ID C025
N-?Carbamoyl-?DL-?aspartic acid (Ureidosuccinic acid) is a precursor of nucleic acid pyrimidines[1].
同义名列表
33 个代谢物同义名
Ureidosuccinic acid, cobalt (+2), (1:1) salt,(L)-isomer; Ureidosuccinic acid, zinc (1:1) salt, (L)-isomer; Ureidosuccinic acid, maganeese (+2), (1:1) salt; (2S)-2-(carbamoylamino)butanedioic acid; N-(Aminocarbonyl)-L-aspartic acid; Ureidosuccinic acid, (D)-isomer; Ureidosuccinic acid, (L)-isomer; N-Carbamoyl-DL-aspartic acid; N-(Aminocarbonyl)-L-aspartate; N-Carbamoyl-S-aspartic acid; N-Carbamoyl-D-aspartic acid; N-Carbamoyl-L-aspartic acid; L-N-Carbamoylaspartic acid; Carbamoyl-DL-aspartic acid; Carbamyl-L-aspartic acid; 2-Ureidobutanedioic acid; N-Carbamoylaspartic acid; N-Carbamoyl-S-aspartate; N-Carbamoyl-L-aspartate; Carbamoylaspartic acid; Carbamyl-DL-aspartate; L-Ureidosuccinic acid; Carbamylaspartic acid; Carbamyl-L-aspartate; N-Carbamoylaspartate; 2-Ureidobutanedioate; Ureidosuccinic acid; Carbamoylaspartate; L-Ureidosuccinate; Ureidosuccinate; NCD; Ureidosuccinic acid; N-?Carbamoyl-?DL-?aspartic acid
数据库引用编号
34 个数据库交叉引用编号
- ChEBI: CHEBI:64850
- ChEBI: CHEBI:15859
- KEGG: C00438
- PubChem: 93072
- PubChem: 279
- HMDB: HMDB0000828
- Metlin: METLIN3304
- DrugBank: DB04252
- ChEMBL: CHEMBL1161506
- Wikipedia: Carbamoyl_aspartic_acid
- MetaCyc: CARBAMYUL-L-ASPARTATE
- KNApSAcK: C00007265
- foodb: FDB031033
- chemspider: 84022
- CAS: 13184-27-5
- CAS: 923-37-5
- MoNA: KO000412
- MoNA: PS104807
- MoNA: PR100879
- MoNA: PS104808
- MoNA: KO000413
- MoNA: KO000414
- MoNA: PS104801
- MoNA: KO000411
- MoNA: PS104803
- MoNA: PS104802
- MoNA: KO000415
- PMhub: MS000009545
- PubChem: 3727
- PDB-CCD: NCD
- 3DMET: B00115
- NIKKAJI: J39.568D
- RefMet: Carbamoylaspartate
- medchemexpress: HY-128425
分类词条
相关代谢途径
PlantCyc(0)
代谢反应
47 个相关的代谢反应过程信息。
Reactome(9)
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Nucleotide metabolism:
H2O + XTP ⟶ PPi + XMP
- Nucleobase biosynthesis:
ATP + H2O + L-Gln + XMP ⟶ AMP + GMP + L-Glu + PPi
- Pyrimidine biosynthesis:
CAP + L-Asp ⟶ N-carbamoyl-L-aspartate + Pi
- De novo synthesis of UMP:
CAP + L-Asp ⟶ N-carbamoyl-L-aspartate + Pi
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Nucleotide metabolism:
H2O + XTP ⟶ PPi + XMP
- Nucleobase biosynthesis:
ATP + H2O + L-Gln + XMP ⟶ AMP + GMP + L-Glu + PPi
- Pyrimidine biosynthesis:
CAP + L-Asp ⟶ N-carbamoyl-L-aspartate + Pi
BioCyc(5)
- uridine-5'-phosphate biosynthesis:
H+ + orotidine-5'-phosphate ⟶ CO2 + UMP
- pyrimidine ribonucleotides de novo biosynthesis:
H+ + orotidine-5'-phosphate ⟶ CO2 + UMP
- superpathway of histidine, purine, and pyrimidine biosynthesis:
glt + imidazole acetol-phosphate ⟶ 2-oxoglutarate + L-histidinol-phosphate
- pyrimidine ribonucleotides de novo biosynthesis:
H+ + orotidine-5'-phosphate ⟶ CO2 + UMP
- uridine-5'-phosphate biosynthesis:
H+ + orotidine-5'-phosphate ⟶ CO2 + UMP
WikiPathways(0)
Plant Reactome(0)
INOH(3)
- Alanine,Aspartic acid and Asparagine metabolism ( Alanine,Aspartic acid and Asparagine metabolism ):
H2O + N-Acetyl-L-aspartic acid ⟶ Acetic acid + L-Aspartic acid
- Pyrimidine Nucleotides and Nucleosides metabolism ( Pyrimidine Nucleotides and Nucleosides metabolism ):
Deoxy-cytidine + H2O ⟶ Deoxy-uridine + NH3
- (S)-Dihydro-orotic acid + H2O = N-Carbamoyl-L-aspartic acid ( Pyrimidine Nucleotides and Nucleosides metabolism ):
N-Carbamoyl-L-aspartic acid ⟶ (S)-Dihydro-orotic acid + H2O
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(30)
- Hypoacetylaspartia:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- beta-Ureidopropionase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- UMP Synthase Deficiency (Orotic Aciduria):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Dihydropyrimidinase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Aspartate Metabolism:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- beta-Ureidopropionase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Canavan Disease:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- Dihydropyrimidinase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Hypoacetylaspartia:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- UMP Synthase Deficiency (Orotic Aciduria):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Aspartate Metabolism:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- Aspartate Metabolism:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Aspartate Metabolism:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Canavan Disease:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Aspartate Metabolism:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- Pyrimidine Metabolism:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- beta-Ureidopropionase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Aspartate Metabolism:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- Dihydropyrimidinase Deficiency:
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Hypoacetylaspartia:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
- UMP Synthase Deficiency (Orotic Aciduria):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy):
Deoxycytidine + Water ⟶ Ammonia + Deoxyuridine
- Canavan Disease:
N-Acetyl-L-aspartic acid + Water ⟶ Acetic acid + L-Aspartic acid
PharmGKB(0)
5 个相关的物种来源信息
- 3702 - Arabidopsis thaliana: 10.1016/J.PLAPHY.2005.01.003
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
- 29760 - Vitis vinifera: 10.1016/J.DIB.2020.106469
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Sandra Witz, Benjamin Jung, Sarah Fürst, Torsten Möhlmann. De novo pyrimidine nucleotide synthesis mainly occurs outside of plastids, but a previously undiscovered nucleobase importer provides substrates for the essential salvage pathway in Arabidopsis.
The Plant cell.
2012 Apr; 24(4):1549-59. doi:
10.1105/tpc.112.096743
. [PMID: 22474184] - Reed B Wickner, Dmitry Kryndushkin, Frank Shewmaker, Ryan McGlinchey, Herman K Edskes. Study of amyloids using yeast.
Methods in molecular biology (Clifton, N.J.).
2012; 849(?):321-46. doi:
10.1007/978-1-61779-551-0_22
. [PMID: 22528100] - Zhang Junjing, Zhao Yan, Zhao Baolu. Scavenging effects of dexrazoxane on free radicals.
Journal of clinical biochemistry and nutrition.
2010 Nov; 47(3):238-45. doi:
10.3164/jcbn.10-64
. [PMID: 21103033] - Shalaka Samant, Hyunwoo Lee, Mahmood Ghassemi, Juan Chen, James L Cook, Alexander S Mankin, Alexander A Neyfakh. Nucleotide biosynthesis is critical for growth of bacteria in human blood.
PLoS pathogens.
2008 Feb; 4(2):e37. doi:
10.1371/journal.ppat.0040037
. [PMID: 18282099] - Herman K Edskes, Benedetta M Naglieri, Reed B Wickner. Nitrogen source and the retrograde signalling pathway affect detection, not generation, of the [URE3] prion.
Yeast (Chichester, England).
2006 Aug; 23(11):833-40. doi:
10.1002/yea.1398
. [PMID: 16921555] - Reed B Wickner, Herman K Edskes, Frank Shewmaker. How to find a prion: [URE3], [PSI+] and [beta].
Methods (San Diego, Calif.).
2006 May; 39(1):3-8. doi:
10.1016/j.ymeth.2006.04.009
. [PMID: 16793280] - A B P van Kuilenburg, B T van Maldegem, N G G M Abeling, F A Wijburg, M Duran. Analysis of pyrimidine synthesis de novo intermediates in urine during crisis of a patient with ornithine transcarbamylase deficiency.
Nucleosides, nucleotides & nucleic acids.
2006; 25(9-11):1251-5. doi:
10.1080/15257770600894634
. [PMID: 17065101] - André B P van Kuilenburg, Henk van Lenthe, Monika Löffler, Albert H van Gennip. Analysis of pyrimidine synthesis "de novo" intermediates in urine and dried urine filter- paper strips with HPLC-electrospray tandem mass spectrometry.
Clinical chemistry.
2004 Nov; 50(11):2117-24. doi:
10.1373/clinchem.2004.038869
. [PMID: 15375016] - E S Cleaveland, D W Zaharevitz, J A Kelley, K Paull, D A Cooney, H Ford. Identification of a novel inhibitor (NSC 665564) of dihydroorotate dehydrogenase with a potency equivalent to brequinar.
Biochemical and biophysical research communications.
1996 Jun; 223(3):654-9. doi:
10.1006/bbrc.1996.0950
. [PMID: 8687451] - R B Wickner. [URE3] as an altered URE2 protein: evidence for a prion analog in Saccharomyces cerevisiae.
Science (New York, N.Y.).
1994 Apr; 264(5158):566-9. doi:
10.1126/science.7909170
. [PMID: 7909170] - J Leonora, J M Tieche, R R Steinman. Further evidence for a hypothalamus-parotid gland endocrine axis in the rat.
Archives of oral biology.
1993 Oct; 38(10):911-6. doi:
10.1016/0003-9969(93)90101-q
. [PMID: 8279995] - Y Inoue, T Ohkura, I Matsumoto, P J Rudewicz. Fast atom bombardment tandem mass spectrometric analysis of N-carbamoylamino acids.
Biological mass spectrometry.
1991 Oct; 20(10):593-601. doi:
10.1002/bms.1200201004
. [PMID: 1793737] - S Vasudevan, E Laconi, S E Abanobi, P M Rao, S Rajalakshmi, D S Sarma. Effect of glycine on the induction of orotic aciduria and urinary bladder tumorigenesis in the rat.
Toxicologic pathology.
1987; 15(2):194-7. doi:
10.1177/019262338701500211
. [PMID: 3616403] - A W Mondorf. [Evidence of urinary tubular proteins in inflammatory and toxic kidney damage].
Wiener medizinische Wochenschrift. Supplement.
1975; 27(?):20-3. doi:
NULL
. [PMID: 5816] - R CROKAERT. [Carbamoyl derivatives of amino acids of biological importance. II. N-Carbamoylaspartic acid. Separation technics and determination in urine in rat and man].
Bulletin de la Societe de chimie biologique.
1961; 43(?):1331-8. doi:
NULL
. [PMID: 13882306] - G DELLA PIETRA, E ROGLIANI, S PROCACCINI, C ROGLIANI. [Synthesis of citrulline from carbamylaspartic acid and ornithine in the presence of beef liver and kidney acetonic powders].
Bollettino della Societa italiana di biologia sperimentale.
1957 Jun; 33(6):771-2. doi:
. [PMID: 13499687]