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Showing NP-Card for N-Methylurea (NP0002886)

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Record Information
Version1.0
Created at2020-11-23 19:42:49 UTC
Updated at2021-08-12 19:52:25 UTC
NP-MRD IDNP0002886
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Methylurea
Provided ByBMRBBMRB logo
DescriptionMethylurea belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group. Methylurea is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on Methylurea (PMID: 24642102) (PMID: 34371611) (PMID: 34365445) (PMID: 34135387) (PMID: 33829649) (PMID: 33637850).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002886 (N-Methylurea)


     RDKit          2D

 11 10  0  0  0  0  0  0  0  0999 V2000
    1.3865   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696    0.8576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9284    0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094   -0.5573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452    2.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445    0.4164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1284   -1.2173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -1.6585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    2.1941    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074   -0.6357    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926   -1.8153    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  6
  1  7  1  0
  1  8  1  0
  2  9  1  0
  4 10  1  0
  4 11  1  0
M  END
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3D MOL for NP0002886 (N-Methylurea)

NP0002886
     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.4174    0.0552   -0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452   -0.5619    0.1769 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506    0.0848   -0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0609   -0.5847   -0.5524 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329    1.4537   -0.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2422   -0.5148    0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3788    1.0853    0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594    0.0767   -1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477   -1.5039    0.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028   -1.6101   -0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434    2.0197    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  3  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  4 10  1  0
  5 11  1  0
M  END
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3D SDF for NP0002886 (N-Methylurea)


     RDKit          2D

 11 10  0  0  0  0  0  0  0  0999 V2000
    1.3865   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696    0.8576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9284    0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094   -0.5573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452    2.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445    0.4164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1284   -1.2173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -1.6585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    2.1941    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074   -0.6357    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926   -1.8153    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  6
  1  7  1  0
  1  8  1  0
  2  9  1  0
  4 10  1  0
  4 11  1  0
M  END
> <DATABASE_ID>
NP0002886

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC(O)=N

> <INCHI_IDENTIFIER>
InChI=1S/C2H6N2O/c1-4-2(3)5/h1H3,(H3,3,4,5)

> <INCHI_KEY>
XGEGHDBEHXKFPX-UHFFFAOYSA-N

> <FORMULA>
C2H6N2O

> <MOLECULAR_WEIGHT>
74.0818

> <EXACT_MASS>
74.048012824

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
7.0873336018898785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methylcarbamimidic acid

> <ALOGPS_LOGP>
-1.13

> <JCHEM_LOGP>
-0.9506080138973042

> <ALOGPS_LOGS>
-0.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.975673098830232

> <JCHEM_PKA_STRONGEST_BASIC>
10.14091726300682

> <JCHEM_POLAR_SURFACE_AREA>
56.11

> <JCHEM_REFRACTIVITY>
28.9759

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylharnstoff

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0002886 (N-Methylurea)

NP0002886
     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.4174    0.0552   -0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452   -0.5619    0.1769 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506    0.0848   -0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0609   -0.5847   -0.5524 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329    1.4537   -0.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2422   -0.5148    0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3788    1.0853    0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594    0.0767   -1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477   -1.5039    0.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028   -1.6101   -0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434    2.0197    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  3  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  4 10  1  0
  5 11  1  0
M  END
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PDB for NP0002886 (N-Methylurea)

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    4    5                                                  
CONECT    3    2                                                            
CONECT    4    1    2                                                       
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for NP0002886 (N-Methylurea)

COMPND    NP0002886
HETATM    1  C1  UNL     1      -1.417   0.055  -0.137  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.145  -0.562   0.177  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.051   0.085  -0.166  1.00  0.00           C  
HETATM    4  N2  UNL     1       2.061  -0.585  -0.552  1.00  0.00           N  
HETATM    5  O1  UNL     1       1.133   1.454  -0.086  1.00  0.00           O  
HETATM    6  H1  UNL     1      -2.242  -0.515   0.292  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.379   1.085   0.245  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.559   0.077  -1.251  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.148  -1.504   0.667  1.00  0.00           H  
HETATM   10  H5  UNL     1       2.003  -1.610  -0.614  1.00  0.00           H  
HETATM   11  H6  UNL     1       0.643   2.020   0.591  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9
CONECT    3    4    4    5
CONECT    4   10
CONECT    5   11
END
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SMILES for NP0002886 (N-Methylurea)

CNC(O)=N
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INCHI for NP0002886 (N-Methylurea)

InChI=1S/C2H6N2O/c1-4-2(3)5/h1H3,(H3,3,4,5)
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View in JSmol
Synonyms
ValueSource
Methyl ureaChEBI
MonomethylureaChEBI
MethylureaKEGG
Chemical FormulaC2H6N2O
Average Mass74.0818 Da
Monoisotopic Mass74.04801 Da
IUPAC NameN-methylcarbamimidic acid
Traditional Namemethylharnstoff
CAS Registry NumberNot Available
SMILES
CNC(O)=N
InChI Identifier
InChI=1S/C2H6N2O/c1-4-2(3)5/h1H3,(H3,3,4,5)
InChI KeyXGEGHDBEHXKFPX-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 NMR1H 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 ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassUreas
Direct ParentUreas
Alternative Parents
Substituents
  • Urea
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen 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-1.1ALOGPS
logP-0.95ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)8.98ChemAxon
pKa (Strongest Basic)10.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area56.11 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.98 m³·mol⁻¹ChemAxon
Polarizability7.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0254670
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID11227
KEGG Compound IDC16363
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11719
PDB IDNot Available
ChEBI ID44383
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Khandelwal N, Abraham SK: Intake of anthocyanidins pelargonidin and cyanidin reduces genotoxic stress in mice induced by diepoxybutane, urethane and endogenous nitrosation. Environ Toxicol Pharmacol. 2014 Mar;37(2):837-43. doi: 10.1016/j.etap.2014.02.012. Epub 2014 Feb 26. [PubMed:24642102 ]
  3. Bara AW, Braszewska A, Kwasniewska J: DNA Methylation-An Epigenetic Mark in Mutagen-Treated Brachypodium distachyon Cells. Plants (Basel). 2021 Jul 9;10(7). pii: plants10071408. doi: 10.3390/plants10071408. [PubMed:34371611 ]
  4. Belenichev I, Gorbachova S, Pavlov S, Bukhtiyarova N, Puzyrenko A, Brek O: NEUROCHEMICAL STATUS OF NITRIC OXIDE IN THE SETTINGS OF THE NORM, ISHEMIC EVENT OF CENTRAL NERVOUS SYSTEM, AND PHARMACOLOGICAL BN INTERVENTION. Georgian Med News. 2021 Jun;(315):169-176. [PubMed:34365445 ]
  5. Nuta O, Bouffler S, Lloyd D, Ainsbury E, Sepai O, Rothkamm K: Investigating the impact of long term exposure to chemical agents on the chromosomal radiosensitivity using human lymphoblastoid GM1899A cells. Sci Rep. 2021 Jun 16;11(1):12616. doi: 10.1038/s41598-021-91957-y. [PubMed:34135387 ]
  6. Zhang JY, Xue WJ, Wang M, Li W, Dong R, Li MT, Sun LP: Discovery of 4,6-Disubstituted Pyrimidine Derivatives as Novel Dual VEGFR2/FGFR1 Inhibitors. Chem Biodivers. 2021 May;18(5):e2100095. doi: 10.1002/cbdv.202100095. Epub 2021 Apr 20. [PubMed:33829649 ]
  7. Danila FR, Thakur V, Chatterjee J, Bala S, Coe RA, Acebron K, Furbank RT, von Caemmerer S, Quick WP: Bundle sheath suberisation is required for C4 photosynthesis in a Setaria viridis mutant. Commun Biol. 2021 Feb 26;4(1):254. doi: 10.1038/s42003-021-01772-4. [PubMed:33637850 ]
  8. Chatterjee J, Coe RA, Acebron K, Thakur V, Yennamalli RM, Danila F, Lin HC, Balahadia CP, Bagunu E, Padhma PPOS, Bala S, Yin X, Rizal G, Dionora J, Furbank RT, von Caemmerer S, Quick WP: A low CO2-responsive mutant of Setaria viridis reveals that reduced carbonic anhydrase limits C4 photosynthesis. J Exp Bot. 2021 Apr 2;72(8):3122-3136. doi: 10.1093/jxb/erab039. [PubMed:33528493 ]
  9. Long F, Lin H, Zhang X, Zhang J, Xiao H, Wang T: Atractylenolide-I Suppresses Tumorigenesis of Breast Cancer by Inhibiting Toll-Like Receptor 4-Mediated Nuclear Factor-kappaB Signaling Pathway. Front Pharmacol. 2020 Dec 8;11:598939. doi: 10.3389/fphar.2020.598939. eCollection 2020. [PubMed:33363472 ]
  10. Rudmann D, Albretsen J, Doolan C, Gregson M, Dray B, Sargeant A, O'Shea D D, Kuklyte J, Power A, Fitzgerald J: Using Deep Learning Artificial Intelligence Algorithms to Verify N-Nitroso-N-Methylurea and Urethane Positive Control Proliferative Changes in Tg-RasH2 Mouse Carcinogenicity Studies. Toxicol Pathol. 2021 Jun;49(4):938-949. doi: 10.1177/0192623320973986. Epub 2020 Dec 8. [PubMed:33287665 ]
  11. Gour A, Dogra A, Wazir P, Singh G, Nandi U: A highly sensitive UPLC-MS/MS method for hydroxyurea to assess pharmacokinetic intervention by phytotherapeutics in rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Oct 1;1154:122283. doi: 10.1016/j.jchromb.2020.122283. Epub 2020 Jul 27. [PubMed:32862024 ]