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Showing NP-Card for biuret (NP0002753)

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Record Information
Version2.0
Created at2020-11-23 19:39:33 UTC
Updated at2021-08-12 19:52:03 UTC
NP-MRD IDNP0002753
Secondary Accession NumbersNone
Natural Product Identification
Common Namebiuret
Provided ByBMRBBMRB logo
DescriptionBiuret, also known as carbamoylurea or allophanamide, belongs to the class of organic compounds known as isoureas. These are organic compounds containing the isourea group, with the general structure R1N(R2)C(=NR3)OR4, or its hydrocarbyl derivatives (R1,R2,R3,R4=H, alkyl, aryl). Biuret exists in all living organisms, ranging from bacteria to humans. Biuret is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. biuret was first documented in 1969 (PMID: 5391979). Based on a literature review a small amount of articles have been published on Biuret (PMID: 24575873) (PMID: 34362043) (PMID: 34358414).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002753 (biuret)


     RDKit          2D

 12 11  0  0  0  0  0  0  0  0999 V2000
   -2.0697   -0.6477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562    0.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359    0.8743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146   -0.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -0.1883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -1.7102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619   -0.8008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910   -1.8634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6494    2.2431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2855   -1.4040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0203    1.1805    0.0000 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
  5  7  2  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  6 11  1  0
  6 12  1  0
M  END
Download

3D MOL for NP0002753 (biuret)

NP0002753
     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
    2.4431   -0.0798   -0.4918 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584   -0.5906   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494   -1.7983    0.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158    0.2460   -0.2235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561   -0.2688    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863    0.6002    0.0332 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3676   -1.4745    0.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868    0.9413   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2374   -0.6894   -0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.2403   -0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4035    1.2625   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1579    0.6109    0.7054 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
  5  7  2  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  6 11  1  0
  6 12  1  0
M  END
Download

3D SDF for NP0002753 (biuret)


     RDKit          2D

 12 11  0  0  0  0  0  0  0  0999 V2000
   -2.0697   -0.6477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562    0.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359    0.8743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146   -0.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -0.1883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -1.7102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619   -0.8008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910   -1.8634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6494    2.2431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2855   -1.4040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0203    1.1805    0.0000 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
  5  7  2  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  6 11  1  0
  6 12  1  0
M  END
> <DATABASE_ID>
NP0002753

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)NC(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H5N3O2/c3-1(6)5-2(4)7/h(H5,3,4,5,6,7)

> <INCHI_KEY>
OHJMTUPIZMNBFR-UHFFFAOYSA-N

> <FORMULA>
C2H5N3O2

> <MOLECULAR_WEIGHT>
103.081

> <EXACT_MASS>
103.038176413

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.471793713102686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(carbamoylamino)formamide

> <ALOGPS_LOGP>
-1.88

> <JCHEM_LOGP>
-1.7087710896666666

> <ALOGPS_LOGS>
-0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.60747722776979

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.795415354945662

> <JCHEM_PKA_STRONGEST_BASIC>
-8.095367009078142

> <JCHEM_POLAR_SURFACE_AREA>
98.20999999999998

> <JCHEM_REFRACTIVITY>
21.385200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
biuret

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002753 (biuret)

NP0002753
     RDKit          3D

 12 11  0  0  0  0  0  0  0  0999 V2000
    2.4431   -0.0798   -0.4918 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584   -0.5906   -0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494   -1.7983    0.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158    0.2460   -0.2235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561   -0.2688    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863    0.6002    0.0332 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3676   -1.4745    0.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868    0.9413   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2374   -0.6894   -0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.2403   -0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4035    1.2625   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1579    0.6109    0.7054 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
  5  7  2  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  6 11  1  0
  6 12  1  0
M  END
Download

PDB for NP0002753 (biuret)

HEADER    PROTEIN                                 05-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-15         0                                  
HETATM    1  N   UNK     0      29.107 -19.790   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      30.441 -19.020   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      31.774 -19.790   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      33.108 -19.020   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      34.442 -19.790   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      30.441 -17.480   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      33.108 -17.480   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4                                                            
CONECT    6    2                                                            
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0002753 (biuret)

COMPND    NP0002753
HETATM    1  N1  UNL     1       2.443  -0.080  -0.492  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.158  -0.591  -0.160  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.049  -1.798   0.192  1.00  0.00           O  
HETATM    4  N2  UNL     1       0.016   0.246  -0.223  1.00  0.00           N  
HETATM    5  C2  UNL     1      -1.256  -0.269   0.108  1.00  0.00           C  
HETATM    6  N3  UNL     1      -2.386   0.600   0.033  1.00  0.00           N  
HETATM    7  O2  UNL     1      -1.368  -1.475   0.460  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.587   0.941  -0.472  1.00  0.00           H  
HETATM    9  H2  UNL     1       3.237  -0.689  -0.752  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.080   1.240  -0.510  1.00  0.00           H  
HETATM   11  H4  UNL     1      -2.404   1.262  -0.773  1.00  0.00           H  
HETATM   12  H5  UNL     1      -3.158   0.611   0.705  1.00  0.00           H  
CONECT    1    2    8    9
CONECT    2    3    3    4
CONECT    4    5   10
CONECT    5    6    7    7
CONECT    6   11   12
END
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SMILES for NP0002753 (biuret)

NC(=O)NC(N)=O
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INCHI for NP0002753 (biuret)

InChI=1S/C2H5N3O2/c3-1(6)5-2(4)7/h(H5,3,4,5,6,7)
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View in JSmol
Synonyms
ValueSource
(Aminocarbonyl)ureaChEBI
AllophanamideChEBI
CarbamoylureaChEBI
Dicarbonimidic diamideChEBI
Imidodicarbonic diamideChEBI
UreidoformamideChEBI
CarbamylureaHMDB
Chemical FormulaC2H5N3O2
Average Mass103.0810 Da
Monoisotopic Mass103.03818 Da
IUPAC Name1-(carbamoylamino)formamide
Traditional Namebiuret
CAS Registry NumberNot Available
SMILES
NC(=O)NC(N)=O
InChI Identifier
InChI=1S/C2H5N3O2/c3-1(6)5-2(4)7/h(H5,3,4,5,6,7)
InChI KeyOHJMTUPIZMNBFR-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, 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 isoureas. These are organic compounds containing the isourea group, with the general structure R1N(R2)C(=NR3)OR4, or its hydrocarbyl derivatives (R1,R2,R3,R4=H, alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentIsoureas
Alternative Parents
Substituents
  • Isourea
  • Carboximidamide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • 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-1.9ALOGPS
logP-1.7ChemAxon
logS-0.14ALOGPS
pKa (Strongest Acidic)11.8ChemAxon
pKa (Strongest Basic)-8.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area98.21 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.39 m³·mol⁻¹ChemAxon
Polarizability8.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0249282
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7625
KEGG Compound IDC06555
BioCyc IDCPD-809
BiGG IDNot Available
Wikipedia LinkBiuret
METLIN IDNot Available
PubChem Compound7913
PDB IDNot Available
ChEBI ID18138
Good Scents IDNot Available
References
General References
  1. Zhao X, Xu C, Wang H, Chen F, Zhang W, Zhao Z, Chen L, Yang S: Application of biuret, dicyandiamide, or urea as a cathode buffer layer toward the efficiency enhancement of polymer solar cells. ACS Appl Mater Interfaces. 2014 Mar 26;6(6):4329-37. doi: 10.1021/am500013s. Epub 2014 Mar 12. [PubMed:24575873 ]
  2. Oltjen RR, Williams EE Jr, Slyter LL, Richardson GV: Urea versus biuret in a roughage diet for steers. J Anim Sci. 1969 Nov;29(5):816-22. doi: 10.2527/jas1969.295816x. [PubMed:5391979 ]
  3. Kabata-Pizuch A, Suder A, Jagielski P, Kubasiak K, Handzlik P, Teleglow A, Marchewka A: Effect of Vibrotherapy on Body Fatness, Blood Parameters and Fibrinogen Concentration in Elderly Men. J Clin Med. 2021 Jul 23;10(15). pii: jcm10153259. doi: 10.3390/jcm10153259. [PubMed:34362043 ]
  4. Boghozian A, Nazem H, Fazilati M, Hejazi SH, Sheikh Sajjadieh M: Toxicity and protein composition of venoms of Hottentotta saulcyi, Hottentotta schach and Androctonus crassicauda, three scorpion species collected in Iran. Vet Med Sci. 2021 Aug 6. doi: 10.1002/vms3.593. [PubMed:34358414 ]