L-citrulline (CHEBI:16349)

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CHEBI:16349 - L-citrulline

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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	ChemicalBook:CB3271542, eMolecules:1970569, eMolecules:481810, Selleckchem:biotin-vitamin-b7, ZINC000035024346

Download	Molfile XML SDF

more structures >>

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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

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Wikipedia	License
Biotin (also known as vitamin B7 or vitamin H) is one of the B vitamins. It is involved in a wide range of metabolic processes, both in humans and in other organisms, primarily related to the utilization of fats, carbohydrates, and amino acids. The name biotin, borrowed from the German Biotin, derives from the Ancient Greek word βίοτος (bíotos; 'life') and the suffix "-in" (a suffix used in chemistry usually to indicate 'forming'). Biotin appears as a white, needle-like crystalline solid.
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

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