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Showing NP-Card for L-Citrulline (NP0334558)

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Record Information
Version2.0
Created at2024-09-10 18:53:47 UTC
Updated at2024-09-10 18:53:47 UTC
NP-MRD IDNP0334558
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Citrulline
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 exists in all living species, ranging from bacteria to plants to humans. In humans, citrulline is involved in the metabolic disorder called the ornithine transcarbamylase deficiency (otc deficiency) pathway. Citrulline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Citrulline, with regard to humans, has been found to be associated with several diseases such as periodontal disease, schizophrenia, tooth decay, and crohn's disease; citrulline has also been linked to the inborn metabolic disorder argininosuccinic aciduria. L-Citrulline was first documented in 2020 (PMID: 34589965). Based on a literature review a small amount of articles have been published on Citrulline (PMID: 34605437) (PMID: 34592055) (PMID: 34587540) (PMID: 34587493).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0334558 (L-Citrulline)


  Mrv1652309042000132D          

 12 11  0  0  1  0            999 V2000
   -0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.1833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  3 10  2  0  0  0  0
  4 11  2  0  0  0  0
  4  5  1  0  0  0  0
  5 12  1  1  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  1  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9  4  1  0  0  0  0
M  END
Download

3D MOL for NP0334558 (L-Citrulline)

HMDB0000904
     RDKit          3D
Citrulline
 25 24  0  0  0  0  0  0  0  0999 V2000
    4.8263   -0.4259   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389    0.3608   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957    1.6080   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637   -0.2349   -0.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2222    0.6324    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -0.1235    0.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    0.8507    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5443    0.1831    0.5635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6210   -0.5802    1.7729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519   -0.6314   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3048   -1.8307   -0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.1084   -1.9053 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6758   -0.1179   -0.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8701   -1.3747    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.2712    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549    1.4012    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373    1.1809   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -0.7281   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376   -0.8324    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2796    1.4671   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0539    1.5333    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    0.9978    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1361   -1.4955    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347   -0.6770    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8576    0.2165   -2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  1
  9 23  1  0
  9 24  1  0
 12 25  1  0
M  END
Download

3D SDF for NP0334558 (L-Citrulline)


  Mrv1652309042000132D          

 12 11  0  0  1  0            999 V2000
   -0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.1833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  3 10  2  0  0  0  0
  4 11  2  0  0  0  0
  4  5  1  0  0  0  0
  5 12  1  1  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  1  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334558

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C6H13N3O3

> <MOLECULAR_WEIGHT>
175.1857

> <EXACT_MASS>
175.095691297

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.34757818367823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-(carbamoylamino)pentanoic acid

> <ALOGPS_LOGP>
-3.27

> <JCHEM_LOGP>
-3.9319578381140263

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.333969157335531

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2682474980163243

> <JCHEM_PKA_STRONGEST_BASIC>
9.225134668659093

> <JCHEM_POLAR_SURFACE_AREA>
118.43999999999998

> <JCHEM_REFRACTIVITY>
41.329

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-citrulline

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0334558 (L-Citrulline)

HMDB0000904
     RDKit          3D
Citrulline
 25 24  0  0  0  0  0  0  0  0999 V2000
    4.8263   -0.4259   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389    0.3608   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957    1.6080   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637   -0.2349   -0.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2222    0.6324    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -0.1235    0.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    0.8507    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5443    0.1831    0.5635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6210   -0.5802    1.7729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519   -0.6314   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3048   -1.8307   -0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.1084   -1.9053 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6758   -0.1179   -0.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8701   -1.3747    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.2712    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549    1.4012    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373    1.1809   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -0.7281   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376   -0.8324    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2796    1.4671   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0539    1.5333    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    0.9978    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1361   -1.4955    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347   -0.6770    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8576    0.2165   -2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  1
  9 23  1  0
  9 24  1  0
 12 25  1  0
M  END
Download

PDB for NP0334558 (L-Citrulline)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.334   0.428   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.667  -0.342   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -4.001   0.428   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   0.428   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.342   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -5.335  -0.342   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.334   0.428   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.342   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -0.342   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.001   1.968   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001   1.968   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       2.667  -1.882   0.000  0.00  0.00           N+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2   10    6                                                  
CONECT    4   11    5    9                                                  
CONECT    5    4   12    7                                                  
CONECT    6    3                                                            
CONECT    7    5    8                                                       
CONECT    8    1    7                                                       
CONECT    9    4                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0334558 (L-Citrulline)

COMPND    HMDB0000904
HETATM    1  N1  UNL     1       4.826  -0.426  -0.291  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.639   0.361  -0.201  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.796   1.608  -0.307  1.00  0.00           O  
HETATM    4  N2  UNL     1       2.364  -0.235  -0.005  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.222   0.632   0.074  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.068  -0.123   0.284  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.218   0.851   0.356  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.544   0.183   0.564  1.00  0.00           C  
HETATM    9  N3  UNL     1      -2.621  -0.580   1.773  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.952  -0.631  -0.621  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.305  -1.831  -0.486  1.00  0.00           O  
HETATM   12  O3  UNL     1      -2.959  -0.108  -1.905  1.00  0.00           O  
HETATM   13  H1  UNL     1       5.676  -0.118  -0.793  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.870  -1.375   0.169  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.318  -1.271   0.073  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.355   1.401   0.862  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.137   1.181  -0.891  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.231  -0.728  -0.656  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.038  -0.832   1.104  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.280   1.467  -0.541  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.054   1.533   1.215  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.305   0.998   0.640  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.136  -1.496   1.724  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.635  -0.677   2.025  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.858   0.216  -2.270  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3    3    4
CONECT    4    5   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   10   22
CONECT    9   23   24
CONECT   10   11   11   12
CONECT   12   25
END
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SMILES for NP0334558 (L-Citrulline)

N[C@@H](CCCNC(N)=O)C(O)=O
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INCHI for NP0334558 (L-Citrulline)

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
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View in JSmol
Synonyms
ValueSource
(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
Chemical FormulaC6H13N3O3
Average Mass175.1857 Da
Monoisotopic Mass175.09569 Da
IUPAC Name(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Traditional NameL-citrulline
CAS Registry NumberNot Available
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 KeyRHGKLRLOHDJJDR-BYPYZUCNSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0000904
DrugBank IDDB00155
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112167
KNApSAcK IDC00001348
Chemspider ID9367
KEGG Compound IDC00327
BioCyc IDL-CITRULLINE
BiGG ID34627
Wikipedia LinkCitrulline
METLIN ID16
PubChem Compound9750
PDB IDNot Available
ChEBI ID16349
Good Scents IDrw1253471
References
General References
  1. Rechiche O, Lee TV, Lott JS: Structural characterization of human peptidyl-arginine deiminase type III by X-ray crystallography. Acta Crystallogr F Struct Biol Commun. 2021 Oct 1;77(Pt 10):334-340. doi: 10.1107/S2053230X21009195. Epub 2021 Sep 21. [PubMed:34605437 ]
  2. Ren W, Wang T, Hu X, Li Y, Ji Z, Guo H, Cao H, Huang J: Development and application of sequential window acquisition of all theoretical mass spectra data acquisition modes on ultra-high-performance liquid chromatography triple-quadrupole/time-of-flight mass spectrometry for metabolic profiling of amino acids in human plasma. J Sep Sci. 2021 Dec;44(23):4209-4221. doi: 10.1002/jssc.202100573. Epub 2021 Oct 13. [PubMed:34592055 ]
  3. Szlosarek PW, Phillips MM, Pavlyk I, Steele J, Shamash J, Spicer J, Kumar S, Pacey S, Feng X, Johnston A, Bomalaski J, Moir G, Lau K, Ellis S, Sheaff M: Expansion Phase 1 Study of Pegargiminase Plus Pemetrexed and Cisplatin in Patients With Argininosuccinate Synthetase 1-Deficient Mesothelioma: Safety, Efficacy, and Resistance Mechanisms. JTO Clin Res Rep. 2020 Sep 3;1(4):100093. doi: 10.1016/j.jtocrr.2020.100093. eCollection 2020 Nov. [PubMed:34589965 ]
  4. Ho SW, El-Nezami H, Corke H, Ho CS, Shah NP: L-citrulline enriched fermented milk with Lactobacillus helveticus attenuates dextran sulfate sodium (DSS) induced colitis in mice. J Nutr Biochem. 2022 Jan;99:108858. doi: 10.1016/j.jnutbio.2021.108858. Epub 2021 Sep 26. [PubMed:34587540 ]
  5. Peters KS, Rivera E, Warden C, Harlow PA, Mitchell SL, Calcutt MW, Samuels DC, Brantley MA Jr: Plasma Arginine and Citrulline are Elevated in Diabetic Retinopathy. Am J Ophthalmol. 2022 Mar;235:154-162. doi: 10.1016/j.ajo.2021.09.021. Epub 2021 Sep 26. [PubMed:34587493 ]