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Showing NP-Card for N-acetyl-L-citrulline (NP0334600)

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Record Information
Version2.0
Created at2024-09-10 19:05:38 UTC
Updated at2024-09-10 19:05:38 UTC
NP-MRD IDNP0334600
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-acetyl-L-citrulline
DescriptionN-acetyl-L-citrulline belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-acetyl-L-citrulline was first documented in 2005 (PMID: 16511126). Based on a literature review a small amount of articles have been published on N-acetyl-L-citrulline (PMID: 16750290) (PMID: 16585758).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334600 (N-acetyl-L-citrulline)


  Mrv2104 05252321372D          

 15 14  0  0  0  0            999 V2000
10034.109910033.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10033.391410033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10032.675910033.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10031.960510033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10031.245110033.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10030.529610033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10029.814310033.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10030.529610034.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.109910032.2256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210031.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10035.540710032.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210030.9853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10035.540710033.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210034.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  1  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
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3D MOL for NP0334600 (N-acetyl-L-citrulline)

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3D SDF for NP0334600 (N-acetyl-L-citrulline)

  Mrv2104 05252321372D          

 15 14  0  0  0  0            999 V2000
10034.109910033.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10033.391410033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10032.675910033.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10031.960510033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10031.245110033.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10030.529610033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10029.814310033.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10030.529610034.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.109910032.2256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210031.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10035.540710032.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210030.9853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210033.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10035.540710033.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10034.824210034.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  1  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@@H](CCCNC(N)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)/t6-/s2

> <INCHI_KEY>
WMQMIOYQXNRROC-MDOHGIEYNA-N

> <FORMULA>
C8H15N3O4

> <MOLECULAR_WEIGHT>
217.225

> <EXACT_MASS>
217.106255975

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.486829058845306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-(carbamoylamino)-2-acetamidopentanoic acid

> <JCHEM_LOGP>
-1.8510329956666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.030159592147145

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.872733207277384

> <JCHEM_PKA_STRONGEST_BASIC>
-1.460434744275114

> <JCHEM_POLAR_SURFACE_AREA>
121.52000000000001

> <JCHEM_REFRACTIVITY>
50.772800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-L-citrulline

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334600 (N-acetyl-L-citrulline)
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PDB for NP0334600 (N-acetyl-L-citrulline)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0    8730.3388728.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8728.9978729.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8727.6628728.365   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8726.3268729.132   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8724.9918728.365   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8723.6558729.132   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8722.3208728.365   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8723.6558730.674   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8730.3388726.821   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8731.6728726.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8733.0098726.821   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8731.6728724.506   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8731.6728729.132   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8733.0098728.365   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8731.6728730.674   0.000  0.00  0.00           O+0
CONECT    1    2    9   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

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3D PDB for NP0334600 (N-acetyl-L-citrulline)
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SMILES for NP0334600 (N-acetyl-L-citrulline)
CC(=O)N[C@@H](CCCNC(N)=O)C(O)=O
Download
INCHI for NP0334600 (N-acetyl-L-citrulline)
InChI=1/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)/t6-/s2
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H15N3O4
Average Mass217.2250 Da
Monoisotopic Mass217.10626 Da
IUPAC Name(2S)-5-(carbamoylamino)-2-acetamidopentanoic acid
Traditional NameN-acetyl-L-citrulline
CAS Registry NumberNot Available
SMILES
CC(=O)N[C@@H](CCCNC(N)=O)C(O)=O
InChI Identifier
InChI=1/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)/t6-/s2
InChI KeyWMQMIOYQXNRROC-MDOHGIEYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated 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 ParentN-acyl-L-alpha-amino acids  
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
    • 

  • Fatty acid
    • 

  • Acetamide
    • 

  • Carboxamide group
    • 

  • Carbonic acid derivative
    • 

  • Secondary carboxylic acid amide
    • 

  • Urea
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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-1.9ChemAxon
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity50.77 m³·mol⁻¹ChemAxon
Polarizability21.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Shi D, Yu X, Roth L, Tuchman M, Allewell NM: Structure of a novel N-acetyl-L-citrulline deacetylase from Xanthomonas campestris. Biophys Chem. 2007 Mar;126(1-3):86-93. doi: 10.1016/j.bpc.2006.05.013. Epub 2006  Jun 5. [PubMed:16750290  ] 
  2. Morizono H, Cabrera-Luque J, Shi D, Gallegos R, Yamaguchi S, Yu X, Allewell NM, Malamy MH, Tuchman M: Acetylornithine transcarbamylase: a novel enzyme in arginine biosynthesis. J Bacteriol. 2006 Apr;188(8):2974-82. doi: 10.1128/JB.188.8.2974-2982.2006. [PubMed:16585758  ] 
  3. Shi D, Yu X, Roth L, Morizono H, Hathout Y, Allewell NM, Tuchman M: Expression, purification, crystallization and preliminary X-ray crystallographic studies of a novel acetylcitrulline deacetylase from Xanthomonas campestris. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Jul 1;61(Pt 7):676-9. doi:  10.1107/S1744309105018051. Epub 2005 Jun 15. [PubMed:16511126  ]