Record Information
Version1.0
Creation date2020-04-20 17:23:44 UTC
Update date2020-09-17 15:38:44 UTC
Primary IDFDB112167
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitrulline
DescriptionCitrulline, 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.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(S)-2-Amino-5-ureidopentanoic acidChEBI
2-Amino-5-ureidovaleric acidChEBI
alpha-Amino-delta-ureidovaleric acidChEBI
CitChEBI
delta-UreidonorvalineChEBI
L-2-Amino-5-ureidovaleric acidChEBI
N(5)-(Aminocarbonyl)-L-ornithineChEBI
N5-(Aminocarbonyl)ornithineChEBI
N5-CarbamoylornithineChEBI
N(delta)-CarbamylornithineChEBI
(S)-2-Amino-5-ureidopentanoateGenerator
2-Amino-5-ureidovalerateGenerator
a-Amino-delta-ureidovalerateGenerator
a-Amino-delta-ureidovaleric acidGenerator
alpha-Amino-delta-ureidovalerateGenerator
Α-amino-δ-ureidovalerateGenerator
Α-amino-δ-ureidovaleric acidGenerator
Δ-ureidonorvalineGenerator
L-2-Amino-5-ureidovalerateGenerator
N(Δ)-carbamylornithineGenerator
a-Amino-δ-ureidovalerateHMDB
a-Amino-δ-ureidovaleric acidHMDB
(2S)-2-Amino-5-(carbamoylamino)pentanoateHMDB
(2S)-2-Amino-5-(carbamoylamino)pentanoic acidHMDB
(S)-2-Amino-5-(aminocarbonyl)aminopentanoateHMDB
(S)-2-Amino-5-(aminocarbonyl)aminopentanoic acidHMDB
2-Amino-5-uredovalerateHMDB
2-Amino-5-uredovaleric acidHMDB
a-Amino-D-ureidovalerateHMDB
a-Amino-D-ureidovaleric acidHMDB
alpha-Amino-gamma-ureidovalerateHMDB
alpha-Amino-gamma-ureidovaleric acidHMDB
Amino-ureidovalerateHMDB
Amino-ureidovaleric acidHMDB
CIRHMDB
CytrullineHMDB
D-UreidonorvalineHMDB
DL-CitrullineHMDB
GammaureidonorvalineHMDB
H-Cit-OHHMDB
L(+)-2-Amino-5-ureidovalerateHMDB
L(+)-2-Amino-5-ureidovaleric acidHMDB
L(+)-CitrullineHMDB
L-2-Amino-5-ureido-valerateHMDB
L-2-Amino-5-ureido-valeric acidHMDB
L-CitrullineHMDB
L-CytrullineHMDB
L-N5-Carbamoyl-ornithineHMDB
N()-CarbamylornithineHMDB
N(5)-(Aminocarbonyl)-DL-ornithineHMDB
N-CarbamylornithineHMDB
N5-(Aminocarbonyl)-L-ornithineHMDB
N5-(Aminocarbonyl)-ornithineHMDB
N5-Carbamoyl-L-ornithineHMDB
N5-CarbamylornithineHMDB
ND-CarbamylornithineHMDB
Ndelta-carbamy-ornithineHMDB
Ndelta-carbamylornithineHMDB
Ngamma-carbamylornithineHMDB
SitrullineHMDB
UreidonorvalineHMDB
UreidovalerateHMDB
Ureidovaleric acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility21.8 g/LALOGPS
logP-3.3ALOGPS
logP-3.9ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)2.27ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability17.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H13N3O3
IUPAC name(2S)-2-amino-5-(carbamoylamino)pentanoic acid
InChI IdentifierInChI=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 KeyRHGKLRLOHDJJDR-BYPYZUCNSA-N
Isomeric SMILESN[C@@H](CCCNC(N)=O)C(O)=O
Average Molecular Weight175.1857
Monoisotopic Molecular Weight175.095691297
Classification
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSCitrulline, non-derivatized, GC-MS Spectrumsplash10-0a4i-0920000000-2d92b63cd5d9648023b8Spectrum
GC-MSCitrulline, 3 TMS, GC-MS Spectrumsplash10-00di-9610000000-2e7cd23afc2adcef35a3Spectrum
GC-MSCitrulline, non-derivatized, GC-MS Spectrumsplash10-0a4i-0920000000-2d92b63cd5d9648023b8Spectrum
GC-MSCitrulline, non-derivatized, GC-MS Spectrumsplash10-00di-9610000000-2e7cd23afc2adcef35a3Spectrum
Predicted GC-MSCitrulline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007o-9100000000-1f8dd2c6648b104639c7Spectrum
Predicted GC-MSCitrulline, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9410000000-37909012a777213f8566Spectrum
Predicted GC-MSCitrulline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrulline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrulline, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrulline, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrulline, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrulline, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrulline, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrulline, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrulline, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-4c1d7af748a47e4899492012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-988fced362fc0da157c92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-0818e0e8bcee126924982012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004j-0900000000-5fa8a338dcd2f2a6bdd22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-16763200aa07f7629ad42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-3900000000-d9cfc5187aa799f6f9782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-10ee9a593e13550bec1c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-45d272576af34c9512a32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-3900000000-6177a284fdea5a3f13062012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-d9456d45e2dbd7a3df102012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-ada57cdc73bda93be4832012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-008a-0904000000-23fbe48f82e515087d682012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-5900000000-78afcbaf8b8b3eabf1742012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-8fb191d4c20fd54b92822012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-da484f0362a8dca5127e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00e9-0900000000-46229b4f77feabb3f8572012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-4aca1022c393602a297d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-0900000000-3bc2eff2e907b7734cc82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-3900000000-2613bf40e3be814da86f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9300000000-e83287bbc060eb9cf6f32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-056r-0900000000-694a8872bdfd7eec1f2b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-08fr-2900000000-15b4711991ea9985fb2b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9300000000-915fbb73e0b728420e4a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-67e60567f5c0627283502012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-9000000000-25140713431edd7c5eea2012-08-31View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C 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
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference