Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:45:11 UTC |
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Updated at | 2022-12-13 23:36:25 UTC |
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CannabisDB ID | CDB004869 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Citrulline |
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Description | Citrulline, also known as Cit or δ-ureidonorvaline, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Citrulline is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Citrulline is a very strong basic compound (based on its pKa). Citrulline exists in all living species, ranging from bacteria to humans. Within humans, citrulline participates in a number of enzymatic reactions. In particular, citrulline can be biosynthesized from carbamoyl phosphate and ornithine; which is catalyzed by the enzyme ornithine carbamoyltransferase, mitochondrial. In addition, citrulline and L-aspartic acid can be converted into argininosuccinic acid through the action of the enzyme argininosuccinate synthase. In humans, citrulline is involved in the metabolic disorder called argininemia. Outside of the human body, Citrulline is found, on average, in the highest concentration within a few different foods, such as wheats, oats, and cucumbers and in a lower concentration in garden onions, saskatoon berries, and swiss chards. Citrulline has also been detected, but not quantified in, several different foods, such as sweet bay, white mustards, fennels, hyacinth beans, and limes. This could make citrulline a potential biomarker for the consumption of these foods. The L-enantiomer of citrulline. Citrulline is a potentially toxic compound. Citrulline, with regard to humans, has been found to be associated with several diseases such as frontotemporal dementia, tooth decay, phosphoenolpyruvate carboxykinase deficiency 1, cytosolic, and pancreatic cancer; citrulline has also been linked to the inborn metabolic disorder argininosuccinic aciduria. Citrulline is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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Synonyms | Value | Source |
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(S)-2-Amino-5-ureidopentanoic acid | ChEBI | 2-Amino-5-ureidovaleric acid | ChEBI | alpha-Amino-delta-ureidovaleric acid | ChEBI | Cit | ChEBI | delta-Ureidonorvaline | ChEBI | L-2-Amino-5-ureidovaleric acid | ChEBI | N(5)-(Aminocarbonyl)-L-ornithine | ChEBI | N5-(Aminocarbonyl)ornithine | ChEBI | N5-Carbamoylornithine | ChEBI | N(delta)-Carbamylornithine | ChEBI | (S)-2-Amino-5-ureidopentanoate | Generator | 2-Amino-5-ureidovalerate | Generator | a-Amino-delta-ureidovalerate | Generator | a-Amino-delta-ureidovaleric acid | Generator | alpha-Amino-delta-ureidovalerate | Generator | Α-amino-δ-ureidovalerate | Generator | Α-amino-δ-ureidovaleric acid | Generator | Δ-ureidonorvaline | Generator | L-2-Amino-5-ureidovalerate | Generator | N(Δ)-carbamylornithine | Generator | a-Amino-δ-ureidovalerate | HMDB | a-Amino-δ-ureidovaleric acid | HMDB | (2S)-2-Amino-5-(carbamoylamino)pentanoate | HMDB | (2S)-2-Amino-5-(carbamoylamino)pentanoic acid | HMDB | (S)-2-Amino-5-(aminocarbonyl)aminopentanoate | HMDB | (S)-2-Amino-5-(aminocarbonyl)aminopentanoic acid | HMDB | 2-Amino-5-uredovalerate | HMDB | 2-Amino-5-uredovaleric acid | HMDB | a-Amino-D-ureidovalerate | HMDB | a-Amino-D-ureidovaleric acid | HMDB | alpha-Amino-gamma-ureidovalerate | HMDB | alpha-Amino-gamma-ureidovaleric acid | HMDB | Amino-ureidovalerate | HMDB | Amino-ureidovaleric acid | HMDB | CIR | HMDB | Cytrulline | HMDB | D-Ureidonorvaline | HMDB | DL-Citrulline | HMDB | Gammaureidonorvaline | HMDB | H-Cit-OH | HMDB | L(+)-2-Amino-5-ureidovalerate | HMDB | L(+)-2-Amino-5-ureidovaleric acid | HMDB | L(+)-Citrulline | HMDB | L-2-Amino-5-ureido-valerate | HMDB | L-2-Amino-5-ureido-valeric acid | HMDB | L-Citrulline | HMDB | L-Cytrulline | HMDB | L-N5-Carbamoyl-ornithine | HMDB | N()-Carbamylornithine | HMDB | N(5)-(Aminocarbonyl)-DL-ornithine | HMDB | N-Carbamylornithine | HMDB | N5-(Aminocarbonyl)-L-ornithine | HMDB | N5-(Aminocarbonyl)-ornithine | HMDB | N5-Carbamoyl-L-ornithine | HMDB | N5-Carbamylornithine | HMDB | ND-Carbamylornithine | HMDB | Ndelta-carbamy-ornithine | HMDB | Ndelta-carbamylornithine | HMDB | Ngamma-carbamylornithine | HMDB | Sitrulline | HMDB | Ureidonorvaline | HMDB | Ureidovalerate | HMDB | Ureidovaleric acid | HMDB |
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Chemical Formula | C6H13N3O3 |
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Average Molecular Weight | 175.19 |
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Monoisotopic Molecular Weight | 175.0957 |
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IUPAC Name | (2S)-2-amino-5-(carbamoylamino)pentanoic acid |
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Traditional Name | L-citrulline |
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CAS Registry Number | 372-75-8 |
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SMILES | N[C@@H](CCCNC(N)=O)C(O)=O |
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InChI Identifier | InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1 |
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InChI Key | RHGKLRLOHDJJDR-BYPYZUCNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - L-alpha-amino acid
- Fatty acid
- Isourea
- Amino acid
- Carboximidic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Carboximidamide
- Amine
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Primary aliphatic amine
- Organopnictogen compound
- Imine
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 235.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 212 mg/mL | Not Available | logP | -3.19 | SANGSTER (1994) |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Citrulline, non-derivatized, GC-MS Spectrum | splash10-0a4i-0920000000-2d92b63cd5d9648023b8 | Spectrum | GC-MS | Citrulline, 3 TMS, GC-MS Spectrum | splash10-00di-9610000000-2e7cd23afc2adcef35a3 | Spectrum | GC-MS | Citrulline, non-derivatized, GC-MS Spectrum | splash10-0a4i-0920000000-2d92b63cd5d9648023b8 | Spectrum | GC-MS | Citrulline, non-derivatized, GC-MS Spectrum | splash10-00di-9610000000-2e7cd23afc2adcef35a3 | Spectrum | Predicted GC-MS | Citrulline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-007o-9100000000-1f8dd2c6648b104639c7 | Spectrum | Predicted GC-MS | Citrulline, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dl-9410000000-37909012a777213f8566 | Spectrum | Predicted GC-MS | Citrulline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citrulline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citrulline, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citrulline, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citrulline, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citrulline, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citrulline, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citrulline, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citrulline, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-0900000000-4c1d7af748a47e489949 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-988fced362fc0da157c9 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-0818e0e8bcee12692498 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-004j-0900000000-5fa8a338dcd2f2a6bdd2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-004i-0900000000-16763200aa07f7629ad4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03di-3900000000-d9cfc5187aa799f6f978 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0a4i-0900000000-10ee9a593e13550bec1c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-004i-0900000000-45d272576af34c9512a3 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-3900000000-6177a284fdea5a3f1306 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0a4i-0900000000-d9456d45e2dbd7a3df10 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-004i-0900000000-ada57cdc73bda93be483 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-008a-0904000000-23fbe48f82e515087d68 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-5900000000-78afcbaf8b8b3eabf174 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-8fb191d4c20fd54b9282 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0900000000-da484f0362a8dca5127e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00e9-0900000000-46229b4f77feabb3f857 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-001i-0900000000-4aca1022c393602a297d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-001i-0900000000-3bc2eff2e907b7734cc8 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-001i-3900000000-2613bf40e3be814da86f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9300000000-e83287bbc060eb9cf6f3 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-056r-0900000000-694a8872bdfd7eec1f2b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-08fr-2900000000-15b4711991ea9985fb2b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00di-9300000000-915fbb73e0b728420e4a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-00di-9000000000-67e60567f5c062728350 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-00di-9000000000-25140713431edd7c5eea | 2012-08-31 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | 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) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Arginine and Proline Metabolism | | | Aspartate Metabolism | | | Urea Cycle | | | Canavan Disease | | Not Available | Hypoacetylaspartia | | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | |
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Metal Bindings | |
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Receptors | |
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Transcriptional Factors | |
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Concentrations Data |
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Alien Dawg | Detected and Quantified | 0.0731 mg/g dry wt | | details | Gabriola | Detected and Quantified | 0.0657 mg/g dry wt | | details | Island Honey | Detected and Quantified | 0.0557 mg/g dry wt | | details | Quadra | Detected and Quantified | 0.0297 mg/g dry wt | | details | Sensi Star | Detected and Quantified | 0.0237 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.0583 mg/g dry wt | | details |
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External Links |
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HMDB ID | HMDB0000904 |
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DrugBank ID | DB00155 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB011841 |
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KNApSAcK ID | C00001348 |
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Chemspider ID | 9367 |
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KEGG Compound ID | C00327 |
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BioCyc ID | L-CITRULLINE |
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BiGG ID | 34627 |
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Wikipedia Link | Citrulline |
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METLIN ID | 16 |
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PubChem Compound | 9750 |
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PDB ID | Not Available |
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ChEBI ID | 16349 |
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References |
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General References | Not Available |
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