L-Citrulline (BioCAD00000012988)

blood cerebrospinal fluid (csf) feces saliva sweat urine bladder epidermis fibroblasts intestine kidney liver neuron placenta platelet prostate

Metabolite Card

Formula: C6H13N3O3 (175.0957)
SMILES: N[C@@H](CCCNC(N)=O)C(O)=O

Synonyms [en]

L-citrulline; citrulline; 2-Amino-5-ureidovaleric acid; N5-carbamoylornithine; delta-Ureidonorvaline; L-2-Amino-5-ureidovaleric acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

L-Citrulline. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000012988). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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 has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. 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. 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. Citrulline has also been found to be associated with several diseases such as ulcerative colitis, rheumatoid arthritis, and citrullinemia type II. Citrulline has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and fumarase deficiency. Outside of the human body, citrulline is found, on average, in the highest concentration in a few different foods such as wheats, oats, and cucumbers and in a lower concentration in swiss chards, yellow wax beans, and potato. Citrulline has also been detected, but not quantified in several different foods, such as epazotes, lotus, common buckwheats, strawberry guava, and italian sweet red peppers. Citrulline is a potentially toxic compound. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. It is also produced from arginine as a byproduct of the reaction catalyzed by NOS family (NOS; EC1.14.13.39).

Mitochondria
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 372-75-8
  • CAS Registry Number: 94740-46-2
  • PubChem: 3621
  • PubChem: 6992098
  • PubChem: 833
  • PubChem: 9750
  • ChEBI: ChEBI:16349
  • ChEBI: ChEBI:18211
  • HMDB: HMDB0000904
  • HMDB: HMDB00904
  • KEGG: C00327
  • BioCyc: L-CITRULLINE
  • NCBI MeSH: Citrulline
  • Wikipedia: Citrulline
  • DrugBank: DB00155
  • RefMet: RM0136022
  • MoNA: KNA00097
  • MoNA: KNA00099
  • MoNA: KNA00100
  • MoNA: KNA00439
  • MoNA: KNA00440
  • MoNA: KNA00441
  • MoNA: KNA00442
  • MoNA: KNA00804
  • MoNA: KNA00805
  • MoNA: KNA00806
  • MoNA: KNA00807
  • MoNA: KO000391
  • MoNA: KO000392
  • MoNA: KO000393
  • MoNA: KO000394
  • MoNA: KO000395
  • MoNA: KO002527
  • MoNA: KO002528
  • MoNA: KO002529
  • MoNA: KO002530
  • MoNA: KO002531
  • MoNA: MT000038
  • MoNA: OUF00141
  • MoNA: PB000431
  • MoNA: PB000432
  • MoNA: PB000433
  • MoNA: PB000434
  • MoNA: PB000435
  • MoNA: PM000949
  • MoNA: PM000996
  • MoNA: PR100448
  • MoNA: PR100901
  • MoNA: PS118901
  • MoNA: PS118902
  • MoNA: PS118903
  • MoNA: PS118904
  • MoNA: PS118905
  • MoNA: PS118907
  • MoNA: PT111890
  • MoNA: PT211890
  • MoNA: VF-NPL-LTQ000241
  • MoNA: VF-NPL-LTQ000242
  • MoNA: VF-NPL-QEHF000502
  • MoNA: VF-NPL-QEHF000503
  • MoNA: VF-NPL-QEHF000504
  • MoNA: VF-NPL-QEHF000505
  • MoNA: VF-NPL-QEHF000506
  • MoNA: VF-NPL-QEHF000507
  • MoNA: VF-NPL-QEHF000508
  • MoNA: VF-NPL-QEHF000509
  • MoNA: VF-NPL-QEHF000510
  • Coconut NaturalProduct: CNP0209633.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00111 1.14.13.39 N-(omega)-hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
KEGG:R00552 3.5.3.6 L-arginine iminohydrolase
KEGG:R00557 1.14.13.39 L-arginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
KEGG:R00665 3.5.1.20 L-citrulline N5-carbamoyldihydrolase
KEGG:R01398 2.1.3.3 carbamoyl-phosphate:L-ornithine carbamoyltransferase
KEGG:R01954 6.3.4.5 L-citrulline:L-aspartate ligase (AMP-forming)
KEGG:R02513 3.5.3.18 Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
KEGG:R09107 3.5.1.16 N-acetyl-L-citrulline amidohydrolase
KEGG:R10106 L-arginine,NADH:oxygen oxidoreductase (nitric-oxide-forming)
KEGG:R10108 2 C05933 + C00004 + C00080 + 2 C00007<=>2 C00327 + 2 C00533 + C00003 + 2 C00001
KEGG:R11711 1.14.14.47 L-arginine,reduced-flavodoxin:oxygen oxidoreductase (nitric-oxide-forming)
KEGG:R11713 1.14.14.47 2 C05933 + C02745 + 2 C00007<=>2 C00327 + 2 C00533 + C02869 + 2 C00001
BioCyc:ARGSUCCINSYN-RXN 6.3.4.5 L-ASPARTATE + L-CITRULLINE + ATP --> PROTON + L-ARGININO-SUCCINATE + PPI + AMP
BioCyc:ORNCARBAMTRANSFER-RXN 2.1.3.3 L-ORNITHINE + CARBAMOYL-P<=>PROTON + L-CITRULLINE + Pi
BioCyc:RXN-13482 2.1.3.3 L-ORNITHINE + CARBAMOYL-P<=>PROTON + L-CITRULLINE + Pi
BioCyc:RXN-13567 2 CPD-13518 + Reduced-flavodoxins + 2 OXYGEN-MOLECULE --> 2 L-CITRULLINE + 2 NITRIC-OXIDE + Oxidized-flavodoxins + 2 WATER + 2 PROTON
BioCyc:DIMETHYLARGININASE-RXN 3.5.3.18 WATER + CPD-596 --> DIMETHYLAMINE + L-CITRULLINE
BioCyc:RXN-7933 3.5.1.16 CPD-7224 + WATER --> L-CITRULLINE + ACET
BioCyc:NITRIC-OXIDE-SYNTHASE-RXN 1.14.13.39 2 ARG + 3 NADPH + PROTON + 4 OXYGEN-MOLECULE --> 2 L-CITRULLINE + 2 NITRIC-OXIDE + 3 NADP + 4 WATER
BioCyc:RXN-13565 2 CPD-13518 + NADPH + 2 OXYGEN-MOLECULE --> 2 L-CITRULLINE + 2 NITRIC-OXIDE + NADP + 2 WATER + PROTON
View More
Organism Source

Taxonomy Source

  1. A new engineered strain of Saccharomyces cerevisiae [n.a.] [ncbi taxid: ]
  2. Amelanchier alnifolia [ncbi taxid: 32219]
  3. Ammoides pusilla [ncbi taxid: 386051]
  4. Amomum melegueta [ncbi taxid: ]
  5. Arabidopsis thaliana [ncbi taxid: 3702]
  6. Astragalus angustifolius [ncbi taxid: 1302566]
  7. Astragalus siculus [ncbi taxid: 3391572]
  8. Avena sativa [ncbi taxid: 4498]
  9. Beta vulgaris [ncbi taxid: 161934]
  10. Carpesium triste [ncbi taxid: 1161924]
  11. Chondria armata [ncbi taxid: 860625]
  12. Citrullus vulgaris [ncbi taxid: ]
  13. Coriolopsis gallica [ncbi taxid: 76126]
  14. Cucumis melo [ncbi taxid: 3656]
  15. Cucumis sativus [ncbi taxid: 3659]
  16. Cucurbita pepo [ncbi taxid: 3663]
  17. Escherichia coli [ncbi taxid: 562]
  18. Eucalyptus camaldulensis [ncbi taxid: 34316]
  19. Frasera albicaulis [ncbi taxid: 137093]
  20. Glycyrrhiza glabra [ncbi taxid: 49827]
  21. Guizotia scabra [ncbi taxid: 413573]
  22. Homo sapiens [ncbi taxid: 9606]
  23. Hyla arborea [ncbi taxid: 121869]
  24. Lactuca sativa [ncbi taxid: 4236]
  25. Leontice robustum [ncbi taxid: ]
  26. Litchi chinensis [ncbi taxid: 151069]
  27. Lolium rigidum [ncbi taxid: 89674]
  28. Mollugo hirta [ncbi taxid: ]
  29. Nezara viridula [ncbi taxid: 85310]
  30. Pastinaca sativa [ncbi taxid: 4041]
  31. Phaseolus vulgaris [ncbi taxid: 3885]
  32. Polysiphonia nigra [ncbi taxid: ]
  33. Prunus tomentosa [ncbi taxid: 105667]
  34. Raoulia australis [ncbi taxid: 857097]
  35. Rapanea maximowiczii [ncbi taxid: ]
  36. Rubus idaeus [ncbi taxid: 32247]
  37. Saccharomyces cerevisiae [ncbi taxid: 4932]
  38. Senecio chionophilus [ncbi taxid: ]
  39. Sesamum indicum [ncbi taxid: 4182]
  40. Solanum tuberosum [ncbi taxid: 4113]
  41. Ulmus campestris [ncbi taxid: ]
  42. Ustilaginoidea virens [ncbi taxid: 1159556]
  43. Xestospongia vanilla [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:TRYPANO_ARG+POLYAMINE-SYN superpathway of arginine and polyamine biosynthesis
BioCyc:LEISH_PWY-4984 urea cycle
BioCyc:TRYPANO_ARGSYN-PWY arginine biosynthesis I
BioCyc:LEISH_PWY3IU-295 nitric oxide biosynthesis
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-OAU-2744343 Amino acid metabolism
Plant Reactome:R-OAU-1119318 Proline biosynthesis V (from arginine)
Plant Reactome:R-CME-1119263 Arginine biosynthesis I
Plant Reactome:R-TAE-1119263 Arginine biosynthesis I
Plant Reactome:R-FVE-5633340 Citrulline-nitric oxide cycle
Plant Reactome:R-FVE-5655122 Amino acid biosynthesis
Plant Reactome:R-FVE-1119495 Citrulline biosynthesis
Plant Reactome:R-FVE-1119318 Proline biosynthesis V (from arginine)
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-MES-2744343 Amino acid metabolism
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-TDI-2744343 Amino acid metabolism
Plant Reactome:R-TDI-1119318 Proline biosynthesis V (from arginine)
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-DRO-5633340 Citrulline-nitric oxide cycle
View All Pathways