Livestock Metabolome Database: Showing metabocard for Citrulline (LMDB00274)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:12 UTC

Update Date

2021-04-30 20:57:42 UTC

Lmdb

LMDB00274

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Citrulline

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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

Chemical Formula

C₆H₁₃N₃O₃

Average Molecular Weight

175.1857

Monoisotopic Molecular Weight

175.095691297

IUPAC Name

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

Traditional Name

L-citrulline

CAS Registry Number

372-75-8

SMILES

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

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

InChI Key

RHGKLRLOHDJJDR-BYPYZUCNSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

citrulline (CHEBI:16349 )
Other amino acids (C00327 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.3	ALOGPS
logP	-3.9	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	2.27	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	118.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	41.33 m³·mol⁻¹	ChemAxon
Polarizability	17.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0920000000-2d92b63cd5d9648023b8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-9610000000-2e7cd23afc2adcef35a3	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0920000000-2d92b63cd5d9648023b8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-9610000000-2e7cd23afc2adcef35a3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-9100000000-1f8dd2c6648b104639c7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9410000000-37909012a777213f8566	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-4c1d7af748a47e489949	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-988fced362fc0da157c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-0818e0e8bcee12692498	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004j-0900000000-5fa8a338dcd2f2a6bdd2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-16763200aa07f7629ad4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-3900000000-d9cfc5187aa799f6f978	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-10ee9a593e13550bec1c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-45d272576af34c9512a3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-3900000000-6177a284fdea5a3f1306	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-d9456d45e2dbd7a3df10	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-ada57cdc73bda93be483	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-008a-0904000000-23fbe48f82e515087d68	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-5900000000-78afcbaf8b8b3eabf174	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-8fb191d4c20fd54b9282	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-da484f0362a8dca5127e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00e9-0900000000-46229b4f77feabb3f857	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-4aca1022c393602a297d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-0900000000-3bc2eff2e907b7734cc8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-3900000000-2613bf40e3be814da86f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9300000000-e83287bbc060eb9cf6f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-056r-0900000000-694a8872bdfd7eec1f2b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-08fr-2900000000-15b4711991ea9985fb2b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-9300000000-915fbb73e0b728420e4a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9000000000-67e60567f5c062728350	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00di-9000000000-25140713431edd7c5eea	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Kidney
Milk
Plasma
Ruminal Fluid
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected and Quantified	49 +/- 1-55+/-3 uM	Not Available	Porcine	183842	details
Kidney	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Plasma	Detected and Quantified	30.61 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	36.88 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	36.98 uM	Not Available	Porcine	25820777	details
Plasma	Detected and Quantified	37.76 uM	Not Available	Porcine	25820777	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Plasma	Detected and Quantified	125 +/- 7-78+/-13 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	153 +/- 18-66+/-3 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	75 +/- 5-84+/-4 uM	Not Available	Porcine	22513987	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Ruminal Fluid	Detected and Quantified	37 +/- 20 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	177.5222 +/- 60.8678 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	201.12 +/- 63.8895 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	64.903 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	54.171 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	61.078 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	63.418 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	172.65 +/- 76.6375 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	175.8 +/- 49.2815 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	189.512 +/- 93.4123 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	167.36 +/- 79.27 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	0.00776 +/- 0.000605 uM	Not Available	Porcine	19847666	details
Serum	Detected and Quantified	0.00549 +/- 0.000753 uM	Not Available	Porcine	19847666	details
Serum	Detected and Quantified	173.74 +/- 79.4543 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	154.4038 +/- 56.1508 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	69 +/- 4 uM	Not Available	Porcine	183842	details
Serum	Detected and Quantified	185.4385 +/- 78.1129 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	151.7519 +/- 48.2374 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected and Quantified	70.5 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	76.4 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	82.4 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	92.7 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	169.0346 +/- 54.285 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	177.9731 +/- 76.2718 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	158.256 +/- 45.3391 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details