NP-MRD: Showing NP-Card for clofazimina (NP0188110)

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Record Information

Version

2.0

Created at

2022-09-04 04:23:12 UTC

Updated at

2022-09-04 04:23:12 UTC

NP-MRD ID

NP0188110

Secondary Accession Numbers

None

Natural Product Identification

Common Name

clofazimina

Description

Clofazimine, also known as lamprene, 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 a drug which is used for the treatment of lepromatous leprosy, including dapsone-resistant lepromatous leprosy and lepromatous leprosy complicated by erythema nodosum leprosum. Clofazimine is a very strong basic compound (based on its pKa). 3-Isopropylimino-3,5-dihydro-phenazine in which the hydrogen at position 5 is substituted substituted by a 4-chlorophenyl group, and that at position 2 is substituted by a (4-chlorophenyl)amino group. However, it can cause red/brown discolouration of the skin, so other treatments are often preferred in light-skinned patients. clofazimina is found in Streptomyces hygroscopicus. clofazimina was first documented in 1988 (PMID: 3279207). A dark red crystalline solid, clofazimine is an antimycobacterial and is one of the main drugs used for the treatment of multi-bacillary leprosy.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04191212152D          

 33 37  0  0  0  0            999 V2000
    5.9083   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -7.3311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6443   -7.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -8.9872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6443   -8.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0638   -7.3311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0638   -8.9872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -6.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7735   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -4.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1930   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -5.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -5.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0638   -6.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -4.0453    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.9290   -7.3311    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4833   -8.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7735   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1930   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4833   -7.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -7.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -8.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7735   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  2  0  0  0  0
  9  2  1  0  0  0  0
 13  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  3  1  0  0  0  0
  7  4  1  0  0  0  0
 10  5  1  0  0  0  0
  7  6  1  0  0  0  0
 12  6  1  0  0  0  0
  8  6  2  0  0  0  0
 11  7  2  0  0  0  0
 28  9  1  0  0  0  0
 10  9  2  0  0  0  0
 29 10  1  0  0  0  0
 11 21  1  4  0  0  0
 16 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 20 14  1  0  0  0  0
 19 15  2  0  0  0  0
 24 16  1  0  0  0  0
 25 16  2  0  0  0  0
 19 17  1  0  0  0  0
 22 17  1  0  0  0  0
 20 17  2  0  0  0  0
 27 18  2  0  0  0  0
 23 18  1  0  0  0  0
 26 18  1  0  0  0  0
 30 21  1  0  0  0  0
 31 21  1  0  0  0  0
 26 24  2  0  0  0  0
 27 25  1  0  0  0  0
 32 28  2  0  0  0  0
 33 29  2  0  0  0  0
 33 32  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -0.4278   -2.8575   -2.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610   -2.8799   -1.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401   -3.7894   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4967   -1.6253   -1.4945 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0459   -0.6895   -0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -0.7661   -0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966    0.2523    0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8906    0.2084    1.1997 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7142   -0.9212    1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041   -1.0958   -0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2308   -2.1987   -0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3527   -3.1295    0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3911   -4.5506    0.4600 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6644   -2.9652    1.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8358   -1.8512    2.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    1.2506    1.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5660    1.1918    2.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0337    2.2404    3.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2721    3.3691    3.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0187    3.4273    2.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5493    2.3870    2.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373    2.4283    1.5471 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328    1.4249    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    1.4497    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8730    0.4468   -0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481    0.4573   -1.2246 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472    1.5149   -1.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4157    1.2243   -1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3929    2.1855   -1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9988    3.4843   -1.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1698    4.7472   -1.8002 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6580    3.7716   -1.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559    2.8116   -1.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351   -3.4268   -3.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7766   -1.8245   -2.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217   -3.4020   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795   -3.3483   -2.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337   -3.4674    0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695   -4.8198   -1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -3.8233   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521   -1.6220   -0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3215   -0.3746   -0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7760   -2.3355   -1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7322   -3.6712    2.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -1.7491    2.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1457    0.2939    2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0092    2.1742    3.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6734    4.1509    4.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4310    4.3136    3.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545    2.3331    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718   -0.4706   -1.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7656    0.2100   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4521    1.9585   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3715    4.7953   -1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369    3.1519   -1.6529 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 21  2  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  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
 17 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
 20 49  1  0
 19 48  1  0
 18 47  1  0
 17 46  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


  Mrv0541 04191212152D          

 33 37  0  0  0  0            999 V2000
    5.9083   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -7.3311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6443   -7.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -8.9872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6443   -8.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0638   -7.3311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0638   -8.9872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -6.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7735   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -4.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1930   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -5.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9083   -5.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0638   -6.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -4.0453    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.9290   -7.3311    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4833   -8.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7735   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1930   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4833   -7.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -7.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -8.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7735   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430   -7.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430   -8.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  2  0  0  0  0
  9  2  1  0  0  0  0
 13  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  3  1  0  0  0  0
  7  4  1  0  0  0  0
 10  5  1  0  0  0  0
  7  6  1  0  0  0  0
 12  6  1  0  0  0  0
  8  6  2  0  0  0  0
 11  7  2  0  0  0  0
 28  9  1  0  0  0  0
 10  9  2  0  0  0  0
 29 10  1  0  0  0  0
 11 21  1  4  0  0  0
 16 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 20 14  1  0  0  0  0
 19 15  2  0  0  0  0
 24 16  1  0  0  0  0
 25 16  2  0  0  0  0
 19 17  1  0  0  0  0
 22 17  1  0  0  0  0
 20 17  2  0  0  0  0
 27 18  2  0  0  0  0
 23 18  1  0  0  0  0
 26 18  1  0  0  0  0
 30 21  1  0  0  0  0
 31 21  1  0  0  0  0
 26 24  2  0  0  0  0
 27 25  1  0  0  0  0
 32 28  2  0  0  0  0
 33 29  2  0  0  0  0
 33 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188110

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)N=C1C=C2N(C3=CC=C(Cl)C=C3)C3=C(C=CC=C3)N=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

> <INCHI_KEY>
WDQPAMHFFCXSNU-UHFFFAOYSA-N

> <FORMULA>
C27H22Cl2N4

> <MOLECULAR_WEIGHT>
473.396

> <EXACT_MASS>
472.122152138

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
51.51572644632594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.39

> <JCHEM_LOGP>
7.304315287333333

> <ALOGPS_LOGS>
-5.50

> <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

> <ALOGPS_SOLUBILITY>
1.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clofazimina

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      11.029 -14.470   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.704 -13.685   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      11.029 -15.991   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.403 -13.685   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       9.704 -16.776   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.678 -15.991   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.678 -14.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.403 -16.776   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.330 -14.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.330 -15.991   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      15.052 -13.685   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      15.052 -16.776   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.704 -12.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.029 -11.378   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.330 -11.378   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.377 -15.991   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.704  -9.072   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.027 -14.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.330  -9.808   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.029  -9.808   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.052 -12.164   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       9.704  -7.551   0.000  0.00  0.00          Cl+0
HETATM   23 Cl   UNK     0      20.401 -13.685   0.000  0.00  0.00          Cl+0
HETATM   24  C   UNK     0      17.702 -16.776   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.377 -14.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.027 -15.991   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.702 -13.685   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.054 -13.685   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.054 -16.776   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.377 -11.378   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.678 -11.378   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.680 -14.470   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.680 -15.991   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    9   13                                                  
CONECT    3    1    5    8                                                  
CONECT    4    1    7                                                       
CONECT    5    3   10                                                       
CONECT    6    7   12    8                                                  
CONECT    7    4    6   11                                                  
CONECT    8    3    6                                                       
CONECT    9    2   28   10                                                  
CONECT   10    5    9   29                                                  
CONECT   11    7   21                                                       
CONECT   12    6   16                                                       
CONECT   13    2   14   15                                                  
CONECT   14   13   20                                                       
CONECT   15   13   19                                                       
CONECT   16   12   24   25                                                  
CONECT   17   19   22   20                                                  
CONECT   18   27   23   26                                                  
CONECT   19   15   17                                                       
CONECT   20   14   17                                                       
CONECT   21   11   30   31                                                  
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   16   26                                                       
CONECT   25   16   27                                                       
CONECT   26   18   24                                                       
CONECT   27   18   25                                                       
CONECT   28    9   32                                                       
CONECT   29   10   33                                                       
CONECT   30   21                                                            
CONECT   31   21                                                            
CONECT   32   28   33                                                       
CONECT   33   29   32                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
(4-Chloro-phenyl)-[5-(4-chloro-phenyl)-3-isopropylimino-3,5-dihydro-phenazin-2-yl]-amine	ChEBI
3-(p-Chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-phenazine	ChEBI
3-(p-Chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin	ChEBI
Clofazimina	ChEBI
Clofaziminum	ChEBI
N,5-Bis(4-chlorophenyl)-3-(isopropylimino)-3,5-dihydrophenazin-2-amine	ChEBI
Chlofazimine	HMDB
Lamprene	HMDB
N,5-Bis(4-chlorophenyl)-3,5-dihydro-3-((1-methylethyl)imino)-2-phenazinamine	HMDB

Chemical Formula

C₂₇H₂₂Cl₂N₄

Average Mass

473.3960 Da

Monoisotopic Mass

472.12215 Da

IUPAC Name

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

Traditional Name

clofazimina

CAS Registry Number

Not Available

SMILES

CC(C)N=C1C=C2N(C3=CC=C(Cl)C=C3)C3=C(C=CC=C3)N=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

InChI Key

WDQPAMHFFCXSNU-UHFFFAOYSA-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

phenazines (CHEBI:3749 )
monochlorobenzenes (CHEBI:3749 )

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	7.39	ALOGPS
logP	7.3	ChemAxon
logS	-5.5	ALOGPS
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	51.52 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

HMDB0014983

DrugBank ID

DB00845

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

Clofazimine

METLIN ID

Not Available

PubChem Compound

2794

PDB ID

Not Available

ChEBI ID

3749

Good Scents ID

Not Available

References

General References

O'Sullivan JF, Conalty ML, Morrison NE: Clofazimine analogues active against a clofazimine-resistant organism. J Med Chem. 1988 Mar;31(3):567-72. doi: 10.1021/jm00398a013. [PubMed:3279207 ]
LOTUS database [Link]

Showing NP-Card for clofazimina (NP0188110)

MOL for NP0188110 (clofazimina)

3D MOL for NP0188110 (clofazimina)

3D SDF for NP0188110 (clofazimina)

3D-SDF for NP0188110 (clofazimina)

PDB for NP0188110 (clofazimina)

3D PDB for NP0188110 (clofazimina)

SMILES for NP0188110 (clofazimina)

INCHI for NP0188110 (clofazimina)

Structure for NP0188110 (clofazimina)

3D Structure for NP0188110 (clofazimina)