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Showing NP-Card for Mercenene (NP0334565)

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Record Information
Version2.0
Created at2024-09-10 18:55:44 UTC
Updated at2024-09-10 18:55:45 UTC
NP-MRD IDNP0334565
Secondary Accession NumbersNone
Natural Product Identification
Common NameMercenene
DescriptionCarmustine, also known as BCNU or gliadel, belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O. Carmustine is a drug which is used for the treatment of brain tumors, multiple myeloma, hodgkin's disease and non-hodgkin's lymphomas. Carmustine (bis-chloroethylnitrosourea, BCNU, BiCNU) is a medication used mainly for chemotherapy. Carmustine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Carmustine has been detected, but not quantified in, mollusks. This could make carmustine a potential biomarker for the consumption of these foods. It is also used as part of a chemotherapeutic protocol in preparation for hematological stem cell transplantation, a type of bone marrow transplant, in order to reduce the white blood cell count in the recipient. Carmustine is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. It is a nitrogen mustard β-chloro-nitrosourea compound. In the treatment of brain tumours, the U.S. Food and Drug Administration (FDA) approved biodegradable discs infused with carmustine (Gliadel). . The product is now available as a generic version with other manufacturers offering the product licensed in the USA and EU markets. Carmustine is used as an alkylating agent to treat several types of brain cancer including glioma, glioblastoma multiforme, medulloblastoma and astrocytoma), multiple myeloma, and lymphoma (Hodgkin's and non-Hodgkin). They are implanted under the skull during a surgery called a craniotomy. In India it is sold under various brand names, including Consium.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334565 (Mercenene)

262
  Mrv0541 02231214332D          

 12 11  0  0  0  0            999 V2000
    7.3659   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 10  2  0  0  0  0
  4  7  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
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3D MOL for NP0334565 (Mercenene)

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3D SDF for NP0334565 (Mercenene)
262
  Mrv0541 02231214332D          

 12 11  0  0  0  0            999 V2000
    7.3659   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 10  2  0  0  0  0
  4  7  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334565

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClCCNC(=O)N(CCCl)N=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)

> <INCHI_KEY>
DLGOEMSEDOSKAD-UHFFFAOYSA-N

> <FORMULA>
C5H9Cl2N3O2

> <MOLECULAR_WEIGHT>
214.05

> <EXACT_MASS>
213.007181961

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.795479653468988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis(2-chloroethyl)-3-nitrosourea

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.0226562823333332

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.96314288261912

> <JCHEM_PKA_STRONGEST_BASIC>
-5.344505514075846

> <JCHEM_POLAR_SURFACE_AREA>
61.77

> <JCHEM_REFRACTIVITY>
46.9797

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carmustine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334565 (Mercenene)
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PDB for NP0334565 (Mercenene)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 262                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      13.750  -0.770   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -0.770   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       8.415  -2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.082   2.310   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.748   0.000   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.081   0.000   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.748   1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      11.082  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.000   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   10                                                            
CONECT    4    7                                                            
CONECT    5    7    8   10                                                  
CONECT    6    9   10                                                       
CONECT    7    4    5                                                       
CONECT    8    5   11                                                       
CONECT    9    6   12                                                       
CONECT   10    3    5    6                                                  
CONECT   11    1    8                                                       
CONECT   12    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0334565 (Mercenene)
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SMILES for NP0334565 (Mercenene)
ClCCNC(=O)N(CCCl)N=O
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INCHI for NP0334565 (Mercenene)
InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
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Synonyms
ValueSource
BCNUChEBI
BicnuChEBI
Bischloroethyl nitrosoureaChEBI
CarmustinaChEBI
CarmustinumChEBI
GliadelChEBI
N,N'-bis(2-chloroethyl)-N-nitrosoureaChEBI
BischlorethylnitrosoureaHMDB
BischlorethylnitrosureaHMDB
CarmustinHMDB
FIVBHMDB
NitrumonHMDB
1,3-Bis(2-chloroethyl)-1-nitrosoureaHMDB
Chemical FormulaC5H9Cl2N3O2
Average Mass214.0500 Da
Monoisotopic Mass213.00718 Da
IUPAC Name1,3-bis(2-chloroethyl)-3-nitrosourea
Traditional Namecarmustine
CAS Registry NumberNot Available
SMILES
ClCCNC(=O)N(CCCl)N=O
InChI Identifier
InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
InChI KeyDLGOEMSEDOSKAD-UHFFFAOYSA-N
Experimental Spectra
Not Available
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 nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassOrganic carbonic acids and derivatives  
Sub ClassUreas  
Direct ParentNitrosoureas  
Alternative Parents
Substituents
  • Nitrosourea
    • 

  • Semicarbazide
    • 

  • Nitrosamide
    • 

  • Organic n-nitroso compound
    • 

  • Organic nitroso compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Alkyl chloride
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Carbonyl group
    • 

  • Alkyl halide
    • 

  • Organic nitrogen compound
    • 

  • 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
logP1.24ALOGPS
logP1.02ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.96ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.77 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.98 m³·mol⁻¹ChemAxon
Polarizability18.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014407  
DrugBank IDDB00262  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012974  
KNApSAcK IDNot Available
Chemspider ID2480  
KEGG Compound IDC06873  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarmustine  
METLIN IDNot Available
PubChem Compound2578  
PDB IDNot Available
ChEBI ID3423  
Good Scents IDNot Available
References
General ReferencesNot Available