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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:22:06 UTC

Update Date

2021-09-26 23:01:48 UTC

HMDB ID

HMDB0250364

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Laromustine

Description

Laromustine, also known as onrigin, belongs to the class of organic compounds known as sulfonylureas. These are organic compounds containing a sulfonyl group with the structure R-S(=O)2-R', where R' is an urea. Interstrand DNA cross-links are difficult to repair and are toxic to cells. Laromustine is a very weakly acidic compound (based on its pKa). VNP40101M is a novel alkylating agent that has been used in trials studying the treatment of Leukemia, Lymphoma, Lung Cancer, Small Intestine Cancer, and Myelodysplastic Syndromes, among others. In preclinical studies, Cloretazine (VNP40101M) has been combined with other anticancer agents such as cytarabine (Ara-C). In addition, Cloretazine (VNP40101M) or its metabolite, has been shown to be capable of crossing the blood brain barrier in preclinical models. VNP40101M demonstrates a broad spectrum of anticancer activity in preclinical studies, including activity in selected cell lines resistant to other alkylating agents such as BCNU, cyclophosphamide and melphalan. It releases the DNA chloroethylating agent 90CE after entering the blood stream. 90CE chloroethylates the O6 position of guanine residues, ultimately resulting in an interstrand DNA cross-link. VNP40101M is a small molecule that works by damaging DNA. This compound has been identified in human blood as reported by (PMID: 31557052 ). Laromustine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Laromustine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0250364
     RDKit          3D
Laromustine
 31 30  0  0  0  0  0  0  0  0999 V2000
    3.3019   -2.5011    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459   -1.2255    0.2497 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374   -1.1095    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -2.1820   -0.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5734    0.1590    0.1624 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    0.2766    0.0486 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3225    1.0004   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.1648   -2.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509   -0.7675   -2.8676 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427   -0.2512    1.2881 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.0270   -1.3806    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684    0.9408    1.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251   -0.9189    2.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    1.5709    0.3569 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5818    3.0355    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871    1.4810    1.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085    1.6319   -0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7869   -3.2769    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3259   -2.8313   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602   -2.3544    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1802   -0.3321    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    1.7832   -1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    1.5674   -0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418   -0.5064   -1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    0.8197   -2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -0.8558    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -1.8559    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -2.1829    0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0034    3.7444    1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241    2.7689    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    3.5874   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  2  0
 10 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  2  0
 14 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

  Mrv0541 02231218132D          

 17 16  0  0  1  0            999 V2000
    4.5080    2.2688    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955   -0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  9  1  0  0  0  0
  2 13  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  2  0  0  0  0
  3 10  1  0  0  0  0
  3 16  1  0  0  0  0
  8 15  2  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 15  1  0  0  0  0
 11 17  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250364

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H14ClN3O5S2/c1-8-6(11)10(17(3,14)15)9(5-4-7)16(2,12)13/h4-5H2,1-3H3,(H,8,11)

> <INCHI_KEY>
PVCULFYROUOVGJ-UHFFFAOYSA-N

> <FORMULA>
C6H14ClN3O5S2

> <MOLECULAR_WEIGHT>
307.775

> <EXACT_MASS>
307.00633966

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.651419498537226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[N-(2-chloroethyl)methanesulfonamido]-3-methanesulfonyl-1-methylurea

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-1.8627553253333333

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.865650662735352

> <JCHEM_POLAR_SURFACE_AREA>
103.85999999999999

> <JCHEM_REFRACTIVITY>
61.91310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
laromustine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250364
     RDKit          3D
Laromustine
 31 30  0  0  0  0  0  0  0  0999 V2000
    3.3019   -2.5011    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459   -1.2255    0.2497 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374   -1.1095    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -2.1820   -0.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5734    0.1590    0.1624 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    0.2766    0.0486 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3225    1.0004   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.1648   -2.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509   -0.7675   -2.8676 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427   -0.2512    1.2881 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.0270   -1.3806    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684    0.9408    1.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251   -0.9189    2.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    1.5709    0.3569 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5818    3.0355    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871    1.4810    1.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085    1.6319   -0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7869   -3.2769    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3259   -2.8313   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602   -2.3544    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1802   -0.3321    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    1.7832   -1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    1.5674   -0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418   -0.5064   -1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    0.8197   -2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -0.8558    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -1.8559    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -2.1829    0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0034    3.7444    1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241    2.7689    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    3.5874   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  2  0
 10 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  2  0
 14 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.415   4.235   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       8.415  -0.385   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0       4.414   0.385   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0       9.185   0.949   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.645  -1.719   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.644  -0.949   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.184   1.719   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.081  -2.695   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       7.081   0.385   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       5.748  -0.385   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.414  -2.695   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   1.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    4    5    9   13                                             
CONECT    3    6    7   10   16                                             
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8   15                                                            
CONECT    9    2   10   12                                                  
CONECT   10    3    9   15                                                  
CONECT   11   15   17                                                       
CONECT   12    9   14                                                       
CONECT   13    2                                                            
CONECT   14    1   12                                                       
CONECT   15    8   10   11                                                  
CONECT   16    3                                                            
CONECT   17   11                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0250364
HETATM    1  C1  UNL     1       3.302  -2.501   0.214  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.646  -1.225   0.250  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.237  -1.109   0.128  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.593  -2.182  -0.011  1.00  0.00           O  
HETATM    5  N2  UNL     1       0.573   0.159   0.162  1.00  0.00           N  
HETATM    6  N3  UNL     1      -0.762   0.277   0.049  1.00  0.00           N  
HETATM    7  C3  UNL     1      -1.323   1.000  -1.000  1.00  0.00           C  
HETATM    8  C4  UNL     1      -1.815   0.165  -2.168  1.00  0.00           C  
HETATM    9 CL1  UNL     1      -0.451  -0.768  -2.868  1.00  0.00          CL  
HETATM   10  S1  UNL     1      -1.743  -0.251   1.288  1.00  0.00           S  
HETATM   11  C5  UNL     1      -3.027  -1.381   0.748  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.468   0.941   1.891  1.00  0.00           O  
HETATM   13  O3  UNL     1      -1.025  -0.919   2.421  1.00  0.00           O  
HETATM   14  S2  UNL     1       1.550   1.571   0.357  1.00  0.00           S  
HETATM   15  C6  UNL     1       0.582   3.036   0.451  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.387   1.481   1.611  1.00  0.00           O  
HETATM   17  O5  UNL     1       2.508   1.632  -0.799  1.00  0.00           O  
HETATM   18  H1  UNL     1       2.787  -3.277   0.819  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.326  -2.831  -0.860  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.360  -2.354   0.517  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.180  -0.332   0.366  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.656   1.783  -1.453  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.213   1.567  -0.634  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.642  -0.506  -1.896  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.182   0.820  -2.985  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.808  -0.856   0.180  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.516  -1.856   1.617  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.599  -2.183   0.118  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.003   3.744   1.221  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.424   2.769   0.777  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.617   3.587  -0.509  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21
CONECT    3    4    4    5
CONECT    5    6   14
CONECT    6    7   10
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT   10   11   12   12   13
CONECT   10   13
CONECT   11   26   27   28
CONECT   14   15   16   16   17
CONECT   14   17
CONECT   15   29   30   31
END

HMDB0250364
     RDKit          3D
Laromustine
 31 30  0  0  0  0  0  0  0  0999 V2000
    3.3019   -2.5011    0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459   -1.2255    0.2497 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374   -1.1095    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -2.1820   -0.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5734    0.1590    0.1624 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    0.2766    0.0486 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3225    1.0004   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.1648   -2.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509   -0.7675   -2.8676 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427   -0.2512    1.2881 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.0270   -1.3806    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684    0.9408    1.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251   -0.9189    2.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    1.5709    0.3569 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5818    3.0355    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871    1.4810    1.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085    1.6319   -0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7869   -3.2769    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3259   -2.8313   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602   -2.3544    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1802   -0.3321    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    1.7832   -1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    1.5674   -0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418   -0.5064   -1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    0.8197   -2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -0.8558    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -1.8559    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -2.1829    0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0034    3.7444    1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241    2.7689    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    3.5874   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  2  0
 10 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  2  0
 14 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Onrigin	MeSH
1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-((2-methylamino)carbonyl)hydrazine	MeSH
Cloretazine	ChEMBL
VNP40101m	ChEMBL
101m	ChEMBL
Laromustine	MeSH
N-(2-Chloroethyl)-N-[N-(methyl-C-hydroxycarbonimidoyl)methanesulphonamido]methanesulphonamide	Generator

Chemical Formula

C₆H₁₄ClN₃O₅S₂

Average Molecular Weight

307.775

Monoisotopic Molecular Weight

307.00633966

IUPAC Name

3-[N-(2-chloroethyl)methanesulfonamido]-3-methanesulfonyl-1-methylurea

Traditional Name

laromustine

CAS Registry Number

Not Available

SMILES

CNC(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O

InChI Identifier

InChI=1S/C6H14ClN3O5S2/c1-8-6(11)10(17(3,14)15)9(5-4-7)16(2,12)13/h4-5H2,1-3H3,(H,8,11)

InChI Key

PVCULFYROUOVGJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfonylureas. These are organic compounds containing a sulfonyl group with the structure R-S(=O)2-R', where R' is an urea.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Sulfonylureas

Direct Parent

Sulfonylureas

Alternative Parents

Substituents

Sulfonylurea
Sulfonohydrazide
Semicarbazide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Carbonic acid derivative
Organic oxygen compound
Alkyl halide
Alkyl chloride
Organosulfur compound
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0250364)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.01	ALOGPS
logP	-1.9	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.91 m³·mol⁻¹	ChemAxon
Polarizability	26.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.545	30932474
DeepCCS	[M-H]-	157.188	30932474
DeepCCS	[M-2H]-	190.106	30932474
DeepCCS	[M+Na]+	165.639	30932474
AllCCS	[M+H]+	162.4	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	165.1	32859911
AllCCS	[M+Na]+	165.8	32859911
AllCCS	[M-H]-	155.9	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	158.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Laromustine	CNC(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O	3352.2	Standard polar	33892256
Laromustine	CNC(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O	2075.8	Standard non polar	33892256
Laromustine	CNC(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O	2216.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Laromustine,1TMS,isomer #1	CN(C(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O)[Si](C)(C)C	2103.1	Semi standard non polar	33892256
Laromustine,1TMS,isomer #1	CN(C(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O)[Si](C)(C)C	2422.7	Standard non polar	33892256
Laromustine,1TMS,isomer #1	CN(C(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O)[Si](C)(C)C	3398.0	Standard polar	33892256
Laromustine,1TBDMS,isomer #1	CN(C(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O)[Si](C)(C)C(C)(C)C	2314.7	Semi standard non polar	33892256
Laromustine,1TBDMS,isomer #1	CN(C(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O)[Si](C)(C)C(C)(C)C	2683.1	Standard non polar	33892256
Laromustine,1TBDMS,isomer #1	CN(C(=O)N(N(CCCl)S(C)(=O)=O)S(C)(=O)=O)[Si](C)(C)C(C)(C)C	3472.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Laromustine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-9320000000-b91d532a7cfd0864eefa	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laromustine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 10V, Positive-QTOF	splash10-0ae9-2891000000-2c4c0302a52a90e05ae9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 20V, Positive-QTOF	splash10-0uk9-2940000000-050e47d2c96ee4dfc4eb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 40V, Positive-QTOF	splash10-004i-9500000000-2188c22c3bcf0dcb59ee	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 10V, Negative-QTOF	splash10-002b-4091000000-0dd744cc27dfa4853922	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 20V, Negative-QTOF	splash10-01sj-1290000000-8957285f683fedc036f8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 40V, Negative-QTOF	splash10-004i-9200000000-4f65d4b0858c32d7daf3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 10V, Positive-QTOF	splash10-0a4i-0009000000-9d3ae659b216ea5bf2b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 20V, Positive-QTOF	splash10-0zfr-5913000000-36adb02b1b66f792f946	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 40V, Positive-QTOF	splash10-08ms-9300000000-0672e2c7c93c1917ea18	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 10V, Negative-QTOF	splash10-0a4j-1891000000-85756e855eadf110d8c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 20V, Negative-QTOF	splash10-014i-6920000000-6db464e9155c4b0994a3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laromustine 40V, Negative-QTOF	splash10-0059-9000000000-7606cc22e29d9b2ce428	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB05817

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3081349

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Laromustine (HMDB0250364)

MOL for HMDB0250364 (Laromustine)

3D MOL for HMDB0250364 (Laromustine)

3D SDF for HMDB0250364 (Laromustine)

3D-SDF for HMDB0250364 (Laromustine)

PDB for HMDB0250364 (Laromustine)

3D PDB for HMDB0250364 (Laromustine)

SMILES for HMDB0250364 (Laromustine)

INCHI for HMDB0250364 (Laromustine)

Structure for HMDB0250364 (Laromustine)

3D Structure for HMDB0250364 (Laromustine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra