NP-MRD: Showing NP-Card for clofazimine (NP0306951)

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Record Information

Version

2.0

Created at

2022-09-10 23:45:17 UTC

Updated at

2022-09-10 23:45:18 UTC

NP-MRD ID

NP0306951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

clofazimine

Description

(3E)-N,5-bis(4-chlorophenyl)-3-[(propan-2-yl)imino]-3,5-dihydrophenazin-2-amine, also known as lamprene or abbr clo, belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring. clofazimine is found in Streptomyces hygroscopicus. Based on a literature review very few articles have been published on (3E)-N,5-bis(4-chlorophenyl)-3-[(propan-2-yl)imino]-3,5-dihydrophenazin-2-amine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201452D          

 33 37  0  0  0  0            999 V2000
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    0.0091   -3.7965   -0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4710   -3.2987    0.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -4.4315    1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.1821    0.4148 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -0.9607    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823   -0.7214    0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8034    0.5695    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    0.8394    0.0517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0449   -0.2321    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3732   -0.7155    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649   -1.7625    1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480   -2.3491    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9715   -3.6675    0.6854 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5284   -1.8762   -0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6402   -0.8349   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622    2.1138   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9364    2.3356   -0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685    3.6195   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930    4.6676   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1349    4.4263   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735    3.1461   -0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283    2.9173   -0.2890 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204    1.6626   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4818    1.3701   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8926    0.0704    0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -0.2519    0.0574 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567    0.6192    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5079    0.3472   -0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6272    1.1363   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6336    2.2608    0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0596    3.2804    0.1793 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5210    2.5495    0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893    1.7488    0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5018   -3.0441   -1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -4.0831   -1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5703   -4.7291   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443   -3.1292    1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7822   -5.3662    1.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4214   -4.1738    2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2883   -4.3857    0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078   -1.4869    0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -0.2452    2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5293   -2.1485    2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9541   -2.2966   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3924   -0.4667   -1.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6060    1.4908    0.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263    3.8297   -0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8989    5.6671   -0.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    5.2498   -0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1625    2.1984   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5142   -1.2929    0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4923   -0.5418   -1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4866    0.8655   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324    3.4450    1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5520    2.0438    1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 25  5  1  0
 33 27  1  0
 23  7  1  0
 15  9  1  0
 21 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  6 41  1  0
 10 42  1  0
 11 43  1  0
 14 44  1  0
 15 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 24 50  1  0
 26 51  1  0
 28 52  1  0
 29 53  1  0
 32 54  1  0
 33 55  1  0
M  END


  Mrv1652309112201452D          

 33 37  0  0  0  0            999 V2000
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306951

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)\N=C1/C=C2N(C3=CC=C(Cl)C=C3)C3=CC=CC=C3N=C2C=C1NC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H22Cl2N4/c1-17(2)30-24-16-27-25(15-23(24)31-20-11-7-18(28)8-12-20)32-22-5-3-4-6-26(22)33(27)21-13-9-19(29)10-14-21/h3-17,31H,1-2H3/b30-24+

> <INCHI_KEY>
WDQPAMHFFCXSNU-BGABXYSRSA-N

> <FORMULA>
C27H22Cl2N4

> <MOLECULAR_WEIGHT>
473.4

> <EXACT_MASS>
472.1221521

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
51.511660743320164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-N,5-bis(4-chlorophenyl)-3-[(propan-2-yl)imino]-3,5-dihydrophenazin-2-amine

> <JCHEM_LOGP>
7.304315287333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.154113770729865

> <JCHEM_PKA_STRONGEST_BASIC>
9.288935498556162

> <JCHEM_POLAR_SURFACE_AREA>
39.99

> <JCHEM_REFRACTIVITY>
142.5521

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
clofazimine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       6.668   3.850   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31 Cl   UNK     0      -4.001  -2.310   0.000  0.00  0.00          Cl+0
HETATM   32  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9                                                       
CONECT   16    8   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    7   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    5   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Lamprene	Kegg
ABBR clo	Kegg

Chemical Formula

C₂₇H₂₂Cl₂N₄

Average Mass

473.4000 Da

Monoisotopic Mass

472.12215 Da

IUPAC Name

(3E)-N,5-bis(4-chlorophenyl)-3-[(propan-2-yl)imino]-3,5-dihydrophenazin-2-amine

Traditional Name

clofazimine

CAS Registry Number

Not Available

SMILES

CC(C)\N=C1/C=C2N(C3=CC=C(Cl)C=C3)C3=CC=CC=C3N=C2C=C1NC1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C27H22Cl2N4/c1-17(2)30-24-16-27-25(15-23(24)31-20-11-7-18(28)8-12-20)32-22-5-3-4-6-26(22)33(27)21-13-9-19(29)10-14-21/h3-17,31H,1-2H3/b30-24+

InChI Key

WDQPAMHFFCXSNU-BGABXYSRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces hygroscopicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Phenazines and derivatives

Alternative Parents

Substituents

Phenazine
Aniline or substituted anilines
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Pyrazine
Heteroaromatic compound
Secondary ketimine
Azacycle
Secondary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	7.3	ChemAxon
pKa (Strongest Acidic)	16.15	ChemAxon
pKa (Strongest Basic)	9.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.55 m³·mol⁻¹	ChemAxon
Polarizability	51.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2692

KEGG Compound ID

C06915

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for clofazimine (NP0306951)

MOL for NP0306951 (clofazimine)

3D MOL for NP0306951 (clofazimine)

3D SDF for NP0306951 (clofazimine)

3D-SDF for NP0306951 (clofazimine)

PDB for NP0306951 (clofazimine)

3D PDB for NP0306951 (clofazimine)

SMILES for NP0306951 (clofazimine)

INCHI for NP0306951 (clofazimine)

Structure for NP0306951 (clofazimine)

3D Structure for NP0306951 (clofazimine)