L-citrulline (CHEBI:16349)

ChEBI > Main

CHEBI:16349 - L-citrulline

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	L-citrulline

ChEBI ID	CHEBI:16349

ChEBI ASCII Name	L-citrulline

Definition	The L-enantiomer of citrulline.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41489, CHEBI:6203, CHEBI:13092, CHEBI:21257

Supplier Information	ZINC000040164933

Download	Molfile XML SDF

more structures >>

call loadScript javascripts\jsmol\core\package.js

call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode

call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js

Jmol JavaScript applet jmolApplet0_object__4093342510358857__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__4093342510358857__)

call loadScript javascripts\jsmol\core\corestate.z.js

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41489","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__4093342510358857__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"4093342510358857","bgcolor":"#000" }

Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $

java.vendor: j2s

java.version: 0.0

os.name: j2s

Access: ALL

memory: 0.0/0.0

processors available: 1

useCommandThread: false

appletId:jmolApplet0_object (signed)

starting HoverWatcher_1

getValue emulate = null

defaults = "Jmol"

getValue boxbgcolor = null

getValue bgcolor = #000

backgroundColor = "#000"

getValue ANIMFRAMECallback = null

getValue APPLETREADYCallback = Jmol._readyCallback

APPLETREADYCallback = "Jmol._readyCallback"

getValue ATOMMOVEDCallback = null

getValue CLICKCallback = null

getValue ECHOCallback = null

getValue ERRORCallback = null

getValue EVALCallback = null

getValue HOVERCallback = null

getValue LOADSTRUCTCallback = null

getValue MEASURECallback = null

getValue MESSAGECallback = null

getValue MINIMIZATIONCallback = null

getValue PICKCallback = null

getValue RESIZECallback = null

getValue SCRIPTCallback = null

getValue SYNCCallback = null

getValue STRUCTUREMODIFIEDCallback = null

getValue doTranslate = null

language=en_US

getValue popupMenu = null

getValue script = null

Jmol applet jmolApplet0_object__4093342510358857__ ready

call loadScript javascripts\jsmol\core\corescript.z.js

call loadScript javascripts\jsmol\J\script\FileLoadThread.js

starting QueueThread0_2

script 1 started

starting HoverWatcher_3

starting HoverWatcher_4

The Resolver thinks Mol

Marvin 11160710503D

starting HoverWatcher_5

Time for openFile(

Marvin 11160710503D

25 24 0 0 0 0 999 V2000

-1.2234 -2.4455 -2.4851 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.7869 -3.3717 -1.9536 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5972 -2.6257 -3.6587 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2231 -1.0879 -1.8313 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.4522 -0.9229 -1.0460 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.0082 -0.9645 -0.9113 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0082 0.4124 -0.2475 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2063 0.5369 0.6733 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2067 1.8564 1.3089 N 0 0 0 0 0 0 0 0 0 0 0 0

2.1899 2.1916 2.1671 C 0 0 0 0 0 0 0 0 0 0 0 0

3.0761 1.3977 2.4148 O 0 0 0 0 0 0 0 0 0 0 0 0

2.1899 3.4045 2.7520 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.5971 -3.4963 -4.0778 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1769 -0.3151 -2.5988 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4533 -1.6548 -0.3513 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3631 -0.0501 -0.5461 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0552 -1.7369 -0.1435 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9036 -1.0869 -1.4941 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0380 1.1852 -1.0151 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9208 0.5353 0.3356 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1601 -0.2360 1.4409 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1189 0.4140 0.0902 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4989 2.4894 1.1113 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8974 3.6455 3.3702 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4826 4.0382 2.5550 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

3 13 1 0 0 0 0

4 5 1 0 0 0 0

4 6 1 0 0 0 0

4 14 1 0 0 0 0

5 15 1 0 0 0 0

5 16 1 0 0 0 0

6 7 1 0 0 0 0

6 17 1 0 0 0 0

6 18 1 0 0 0 0

7 8 1 0 0 0 0

7 19 1 0 0 0 0

7 20 1 0 0 0 0

8 9 1 0 0 0 0

8 21 1 0 0 0 0

8 22 1 0 0 0 0

9 10 1 0 0 0 0

9 23 1 0 0 0 0

10 11 2 0 0 0 0

10 12 1 0 0 0 0

12 24 1 0 0 0 0

12 25 1 0 0 0 0

M END): 18 ms

reading 25 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

25 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]−. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH. Carbamic acid could be seen as both an amine and carboxylic acid, and therefore an amino acid; however, the attachment of the carboxyl group –COOH directly to the nitrogen atom (without any intermediate carbon chain) makes it behave very differently from the amino acids with intermediate carbon chain. (Glycine NH2CH2COOH is generally considered to be the simplest amino acid.) The hydroxyl group –OH attached to the carbon also excludes it from the amide class. The term "carbamic acid" is also used generically for any compounds of the form RR′NCOOH, where R and R′ are organic groups or hydrogen. Deprotonation of a carbamic acid yields a carbamate anion RR′NCOO−, the salts of which can be relatively stable. Carbamate is also a term used for esters of carbamic acids, such as methyl carbamate H2N−C(=O)−OCH3. The carbamoyl functional group RR′N–C(=O)– (often denoted by Cbm) is the carbamic acid molecule minus the OH part of the carboxyl.
Read full article at Wikipedia

Formula

C6H13N3O3

Net Charge

Average Mass

175.18584

Monoisotopic Mass

175.09569

InChI

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

InChIKey

RHGKLRLOHDJJDR-BYPYZUCNSA-N

SMILES

N[C@@H](CCCNC(N)=O)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Arabidopsis thaliana (NCBI:txid3702)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). EC 1.14.13.39 (nitric oxide synthase) inhibitor An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39). Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. (via citrulline ) hapten Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals. (via citrulline )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. protective agent Synthetic or natural substance which is given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-citrulline (CHEBI:16349) has role Escherichia coli metabolite (CHEBI:76971) L-citrulline (CHEBI:16349) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-citrulline (CHEBI:16349) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908) L-citrulline (CHEBI:16349) has role human metabolite (CHEBI:77746) L-citrulline (CHEBI:16349) has role micronutrient (CHEBI:27027) L-citrulline (CHEBI:16349) has role mouse metabolite (CHEBI:75771) L-citrulline (CHEBI:16349) has role nutraceutical (CHEBI:50733) L-citrulline (CHEBI:16349) has role protective agent (CHEBI:50267) L-citrulline (CHEBI:16349) is a citrulline (CHEBI:18211) L-citrulline (CHEBI:16349) is enantiomer of D-citrulline (CHEBI:49007) L-citrulline (CHEBI:16349) is tautomer of L-citrulline zwitterion (CHEBI:57743)

Incoming	N-acetyl-L-citrulline (CHEBI:49002) has functional parent L-citrulline (CHEBI:16349) N²-succinyl-L-citrulline (CHEBI:51309) has functional parent L-citrulline (CHEBI:16349) L-citrulline-d2 (CHEBI:192078) is a L-citrulline (CHEBI:16349) D-citrulline (CHEBI:49007) is enantiomer of L-citrulline (CHEBI:16349) L-citrulline residue (CHEBI:83397) is substituent group from L-citrulline (CHEBI:16349) L-citrulline zwitterion (CHEBI:57743) is tautomer of L-citrulline (CHEBI:16349)

IUPAC Names

(2S)-2-amino-5-(carbamoylamino)pentanoic acid

L-citrulline

N⁵-carbamoyl-L-ornithine

Synonyms	Sources
(S)-2-Amino-5-ureidopentanoic acid	HMDB
2-Amino-5-ureidovaleric acid	KEGG COMPOUND
α-amino-δ-ureidovaleric acid	ChemIDplus
Cit	ChemIDplus
CITRULLINE	PDBeChem
Citrulline	KEGG COMPOUND
δ-ureidonorvaline	ChemIDplus
L-2-Amino-5-ureidovaleric acid	HMDB
L-Citrulline	KEGG COMPOUND
N⁵-(aminocarbonyl)-L-ornithine	ChemIDplus
N5-(Aminocarbonyl)ornithine	DrugBank
N5-carbamoylornithine	DrugBank
N^δ-carbamylornithine	ChemIDplus

Manual Xrefs	Databases
3103	DrugCentral
C00001348	KNApSAcK
C00327	KEGG COMPOUND
CIR	PDBeChem
Citrulline	Wikipedia
D07706	KEGG DRUG
DB00155	DrugBank
ECMDB00904	ECMDB
HMDB0000904	HMDB
L-CITRULLINE	MetaCyc
YMDB00060	YMDB
View more database links

Registry Numbers	Types	Sources
1725416	Reaxys Registry Number	Reaxys
372-75-8	CAS Registry Number	ChemIDplus
6055157	Beilstein Registry Number	Beilstein
774677	Gmelin Registry Number	Gmelin

Citations	Types	Sources
11862757	PubMed citation	Europe PMC
17190852	PubMed citation	Europe PMC
18022291	PubMed citation	Europe PMC
19173225	PubMed citation	Europe PMC
21067832	PubMed citation	Europe PMC
21915076	PubMed citation	Europe PMC
21955999	PubMed citation	Europe PMC
22119809	PubMed citation	Europe PMC
22345866	PubMed citation	Europe PMC
22348173	PubMed citation	Europe PMC
22387109	PubMed citation	Europe PMC
22388927	PubMed citation	Europe PMC
22402328	PubMed citation	Europe PMC
22402472	PubMed citation	Europe PMC
22512552	PubMed citation	Europe PMC

Last Modified

18 August 2017

CHEBI:16349 - L-citrulline

ChEBI is part of the ELIXIR infrastructure