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Showing NP-Card for 4,5-Dihydroorotic acid (NP0000289)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:11 UTC
NP-MRD IDNP0000289
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,5-Dihydroorotic acid
Description4,5-Dihydroorotic acid, also known as dihydroorotate or hydroorotate is a pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N-alpha-carbethoxyasparagine. It is classified as a secondary amide, a monocarboxylic acid, a pyrimidinemonocarboxylic acid and a N-acylurea. 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. 4,5-Dihydroorotic acid exists in all living species, ranging from bacteria to plants to humans. 4,5-Dihydroorotic acid is synthesized by the enzyme known as Dihydroorotase (EC 3.5.2.3) Which converts carbamoyl aspartic acid into 4,5-dihydroorotic acid as part of the de novo pyrimidine biosynthesis pathway (PMID: 13163076 ). 4,5-Dihydroorotic acid is also a substrate for the enzyme known as dihydroorotate dehydrogenase (DHODH). In mammalian species, DHODH catalyzes the fourth step in the de novo pyrimidine biosynthesis pathway, which involves the ubiquinone-mediated oxidation of dihydroorotate to orotate and the reduction of flavin mononucleotide (FMN) to dihydroflavin mononucleotide (FMNH2). Inhibition of DHODH activity with teriflunomide (an immunomodulatory drug) or expression with RNA interference results in reduced ROS generation and consequent apoptosis of transformed skin and prostate epithelial cells. Mutations in the DHOD gene have been shown to cause Miller syndrome, also known as Genee-Wiedemann syndrome, Wildervanck-Smith syndrome or post-axial acrofacial dystosis (PMID: 19915526 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000289 (4,5-Dihydroorotic acid)

4,5-Dihydroorotic acid.mol
  Mrv1652305261923592D          

 11 11  0  0  0  0            999 V2000
    0.0087    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188   -0.2075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -1.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7101   -0.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7043    1.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247    1.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  1 10  2  0  0  0  0
  1 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000289 (4,5-Dihydroorotic acid)

HMDB0000528
     RDKit          3D
4,5-Dihydroorotic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.0113   -0.2867    1.9855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108   -0.1526    0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690   -1.0434    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480   -0.5257   -0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.1305    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1344    1.2775   -0.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5883   -0.5428    1.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384    0.3591   -1.3895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352    1.1177   -1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    1.9949   -2.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789    0.8455   -0.0049 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3090   -1.2239    1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6844   -2.0337    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877   -1.4247   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879   -0.3425    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4963    0.4773   -2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7421    1.3736    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11  2  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
  8 16  1  0
 11 17  1  0
M  END
Download

3D SDF for NP0000289 (4,5-Dihydroorotic acid)

4,5-Dihydroorotic acid.mol
  Mrv1652305261923592D          

 11 11  0  0  0  0            999 V2000
    0.0087    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188   -0.2075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -1.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7101   -0.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7043    1.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247    1.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  1 10  2  0  0  0  0
  1 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000289

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CC(=O)NC(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)

> <INCHI_KEY>
UFIVEPVSAGBUSI-UHFFFAOYSA-N

> <FORMULA>
C5H6N2O4

> <MOLECULAR_WEIGHT>
158.1121

> <EXACT_MASS>
158.03275669

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.091120354543254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-dioxo-1,3-diazinane-4-carboxylic acid

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-1.5232681353333333

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.713668138573995

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2849203199118633

> <JCHEM_PKA_STRONGEST_BASIC>
-8.186843445720307

> <JCHEM_POLAR_SURFACE_AREA>
95.50000000000001

> <JCHEM_REFRACTIVITY>
31.575400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroorotic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000289 (4,5-Dihydroorotic acid)

HMDB0000528
     RDKit          3D
4,5-Dihydroorotic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.0113   -0.2867    1.9855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4108   -0.1526    0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690   -1.0434    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480   -0.5257   -0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.1305    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1344    1.2775   -0.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5883   -0.5428    1.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384    0.3591   -1.3895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352    1.1177   -1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    1.9949   -2.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789    0.8455   -0.0049 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3090   -1.2239    1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6844   -2.0337    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877   -1.4247   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879   -0.3425    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4963    0.4773   -2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7421    1.3736    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11  2  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
  8 16  1  0
 11 17  1  0
M  END
Download

PDB for NP0000289 (4,5-Dihydroorotic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4,5-Dihydroorotic acid.mol                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       0.016   1.927   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.011   0.387   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.342  -0.387   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.336  -1.927   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667  -2.702   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       0.000  -2.693   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.331  -1.918   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667  -2.683   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.326  -0.378   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.315   2.702   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.353   2.693   0.000  0.00  0.00           O+0
CONECT    1    2   10   11                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2                                                       
CONECT   10    1                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
Download

3D PDB for NP0000289 (4,5-Dihydroorotic acid)

COMPND    HMDB0000528
HETATM    1  O1  UNL     1      -2.011  -0.287   1.985  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.411  -0.153   0.884  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.269  -1.043   0.605  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.648  -0.526  -0.463  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.832   0.131   0.109  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.134   1.277  -0.251  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.588  -0.543   1.039  1.00  0.00           O  
HETATM    8  N1  UNL     1       0.038   0.359  -1.390  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.135   1.118  -1.185  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.490   1.995  -2.027  1.00  0.00           O  
HETATM   11  N2  UNL     1      -1.879   0.846  -0.005  1.00  0.00           N  
HETATM   12  H1  UNL     1       0.309  -1.224   1.555  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.684  -2.034   0.321  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.988  -1.425  -1.063  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.588  -0.343   2.038  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.496   0.477  -2.340  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.742   1.374   0.187  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   12   13
CONECT    4    5    8   14
CONECT    5    6    6    7
CONECT    7   15
CONECT    8    9   16
CONECT    9   10   10   11
CONECT   11   17
END
Download

SMILES for NP0000289 (4,5-Dihydroorotic acid)

OC(=O)C1CC(=O)NC(=O)N1
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INCHI for NP0000289 (4,5-Dihydroorotic acid)

InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)
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View in JSmol
Synonyms
ValueSource
5,6-Dihydro-orotic acidChEBI
DL-Dihydroortotic acidChEBI
Hydroorotic acidChEBI
5,6-Dihydro-orotateGenerator
DL-DihydroortotateGenerator
HydroorotateGenerator
4,5-DihydroorotateGenerator
(+)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylateHMDB
(+)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acidHMDB
(R)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylateHMDB
(R)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acidHMDB
(S)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylateHMDB
(S)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acidHMDB
2,6-Dioxo-hexahydro-pyrimidine-4-carboxylateHMDB
2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acidHMDB
5,6-DihydroorotateHMDB
L-HydroorotateHMDB
L-Hydroorotic acidHMDB
R,S-HydroorotateHMDB
L-DihydroorotateHMDB
4,5-Dihydroorotic acid, (L)-isomerHMDB
DihydroorotateHMDB
4,5-Dihydroorotic acid, (D)-isomerHMDB
4,5-Dihydroorotic acid, (DL)-isomerHMDB
Chemical FormulaC5H6N2O4
Average Mass158.1121 Da
Monoisotopic Mass158.03276 Da
IUPAC Name2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional Namedihydroorotic acid
CAS Registry Number155-54-4
SMILES
OC(=O)C1CC(=O)NC(=O)N1
InChI Identifier
InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)
InChI KeyUFIVEPVSAGBUSI-UHFFFAOYSA-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 Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Escherichia coliBacteria
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • N-acyl urea
  • Pyrimidone
  • Ureide
  • 1,3-diazinane
  • Pyrimidine
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.7 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.58 m³·mol⁻¹ChemAxon
Polarizability13.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000528
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022096
KNApSAcK IDNot Available
Chemspider ID628
KEGG Compound IDC00337
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4,5-Dihydroorotic_acid
METLIN ID5513
PubChem Compound648
PDB IDNot Available
ChEBI ID30865
Good Scents IDNot Available
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]
  3. LIEBERMAN I, KORNBERG A: Enzymatic synthesis and breakdown of a pyrimidine, orotic acid. I. Dihydroortic acid, ureidosuccinic acid, and 5-carboxymethylhydantoin. J Biol Chem. 1954 Apr;207(2):911-24. [PubMed:13163076 ]
  4. Ng SB, Buckingham KJ, Lee C, Bigham AW, Tabor HK, Dent KM, Huff CD, Shannon PT, Jabs EW, Nickerson DA, Shendure J, Bamshad MJ: Exome sequencing identifies the cause of a mendelian disorder. Nat Genet. 2010 Jan;42(1):30-5. doi: 10.1038/ng.499. Epub 2009 Nov 13. [PubMed:19915526 ]
  5. Suzuki M, Sugano H, Matsumoto K, Yamamura M, Ishida R: Synthesis and central nervous system actions of thyrotropin-releasing hormone analogues containing a dihydroorotic acid moiety. J Med Chem. 1990 Aug;33(8):2130-7. doi: 10.1021/jm00170a014. [PubMed:2115588 ]
  6. Tsanov V, Tsanov H: Theoretical Analysis of Anticancer Cellular Effects of Glycoside Amides. Anticancer Agents Med Chem. 2021 Sep 3. pii: ACAMC-EPUB-117670. doi: 10.2174/1871520621666210903122831. [PubMed:34477528 ]