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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (2) Show 3 proteins XML

enzymes (1)transporters (2) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0014983

Secondary Accession Numbers

HMDB14983

Metabolite Identification

Common Name

Clofazimine

Description

A fat-soluble riminophenazine dye used for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients. Clofazimine also has a marked anti-inflammatory effect and is given to control the leprosy reaction, erythema nodosum leprosum. (From AMA Drug Evaluations Annual, 1993, p1619)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

HMDB0014983
     RDKit          3D
Clofazimine
 55 59  0  0  0  0  0  0  0  0999 V2000
   -2.2574    2.4931    3.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.9168    1.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    3.1530    1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857    1.3315    1.2515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.5838    0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4191    0.6026    0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1993   -0.1808   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469   -0.1555   -0.0017 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.6943    0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186    1.9977    0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    2.7200    1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122    2.2018    2.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0448    3.1839    4.2028 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9478    0.9003    3.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701    0.1741    2.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2727   -0.9546   -0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6571   -0.9202   -0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4649   -1.7162   -1.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -2.5499   -2.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5061   -2.5597   -2.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6731   -1.7804   -1.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3349   -1.8155   -1.8967 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307   -1.0337   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -1.0462   -1.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045   -0.2432   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270   -0.1943   -0.5995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8175   -1.0949   -1.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9346   -0.6368   -2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7588   -1.4884   -2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5053   -2.8390   -2.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5714   -3.9362   -3.6377 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -3.3150   -2.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -2.4424   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    2.8350    3.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059    1.6637    3.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249    3.2678    2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    1.3167    2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    3.9592    1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1709    3.4311    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0871    2.9317   -0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049    1.2371    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3416    2.3986   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3841    3.7366    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1068    0.4575    4.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870   -0.8447    2.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355   -0.2821    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5573   -1.7165   -1.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145   -3.1802   -2.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703   -3.2107   -3.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750   -1.6816   -2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5419    0.5828   -0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1158    0.4387   -1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6148   -1.1063   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -4.3832   -2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7674   -2.9015   -0.8421 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  3
  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


  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>
HMDB0014983

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0014983
     RDKit          3D
Clofazimine
 55 59  0  0  0  0  0  0  0  0999 V2000
   -2.2574    2.4931    3.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.9168    1.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    3.1530    1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857    1.3315    1.2515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.5838    0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4191    0.6026    0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1993   -0.1808   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469   -0.1555   -0.0017 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.6943    0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186    1.9977    0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    2.7200    1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122    2.2018    2.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0448    3.1839    4.2028 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9478    0.9003    3.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701    0.1741    2.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2727   -0.9546   -0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6571   -0.9202   -0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4649   -1.7162   -1.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -2.5499   -2.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5061   -2.5597   -2.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6731   -1.7804   -1.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3349   -1.8155   -1.8967 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307   -1.0337   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -1.0462   -1.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045   -0.2432   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270   -0.1943   -0.5995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8175   -1.0949   -1.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9346   -0.6368   -2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7588   -1.4884   -2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5053   -2.8390   -2.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5714   -3.9362   -3.6377 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -3.3150   -2.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -2.4424   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    2.8350    3.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059    1.6637    3.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249    3.2678    2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    1.3167    2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    3.9592    1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1709    3.4311    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0871    2.9317   -0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049    1.2371    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3416    2.3986   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3841    3.7366    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1068    0.4575    4.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870   -0.8447    2.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355   -0.2821    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5573   -1.7165   -1.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145   -3.1802   -2.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703   -3.2107   -3.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750   -1.6816   -2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5419    0.5828   -0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1158    0.4387   -1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6148   -1.1063   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -4.3832   -2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7674   -2.9015   -0.8421 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  3
  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

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

COMPND    HMDB0014983
HETATM    1  C1  UNL     1      -2.257   2.493   3.188  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.676   1.917   1.797  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.155   3.153   1.016  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.586   1.332   1.251  1.00  0.00           N  
HETATM    5  C4  UNL     1      -0.989   0.584   0.487  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.419   0.603   0.629  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.199  -0.181  -0.147  1.00  0.00           C  
HETATM    8  N2  UNL     1       2.547  -0.156  -0.002  1.00  0.00           N  
HETATM    9  C7  UNL     1       3.150   0.694   0.968  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.519   1.998   0.703  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.093   2.720   1.721  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.312   2.202   2.974  1.00  0.00           C  
HETATM   13 CL1  UNL     1       5.045   3.184   4.203  1.00  0.00          CL  
HETATM   14  C11 UNL     1       3.948   0.900   3.249  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.370   0.174   2.227  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.273  -0.955  -0.799  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.657  -0.920  -0.640  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.465  -1.716  -1.427  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.875  -2.550  -2.377  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.506  -2.560  -2.508  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.673  -1.780  -1.742  1.00  0.00           C  
HETATM   22  N3  UNL     1       1.335  -1.815  -1.897  1.00  0.00           N  
HETATM   23  C19 UNL     1       0.531  -1.034  -1.125  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.836  -1.046  -1.258  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.605  -0.243  -0.458  1.00  0.00           C  
HETATM   26  N4  UNL     1      -3.027  -0.194  -0.600  1.00  0.00           N  
HETATM   27  C22 UNL     1      -3.818  -1.095  -1.326  1.00  0.00           C  
HETATM   28  C23 UNL     1      -4.935  -0.637  -2.023  1.00  0.00           C  
HETATM   29  C24 UNL     1      -5.759  -1.488  -2.715  1.00  0.00           C  
HETATM   30  C25 UNL     1      -5.505  -2.839  -2.743  1.00  0.00           C  
HETATM   31 CL2  UNL     1      -6.571  -3.936  -3.638  1.00  0.00          CL  
HETATM   32  C26 UNL     1      -4.415  -3.315  -2.066  1.00  0.00           C  
HETATM   33  C27 UNL     1      -3.587  -2.442  -1.368  1.00  0.00           C  
HETATM   34  H1  UNL     1      -3.147   2.835   3.722  1.00  0.00           H  
HETATM   35  H2  UNL     1      -1.806   1.664   3.758  1.00  0.00           H  
HETATM   36  H3  UNL     1      -1.525   3.268   2.961  1.00  0.00           H  
HETATM   37  H4  UNL     1      -3.584   1.317   2.048  1.00  0.00           H  
HETATM   38  H5  UNL     1      -2.429   3.959   1.234  1.00  0.00           H  
HETATM   39  H6  UNL     1      -4.171   3.431   1.308  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.087   2.932  -0.048  1.00  0.00           H  
HETATM   41  H8  UNL     1       0.905   1.237   1.355  1.00  0.00           H  
HETATM   42  H9  UNL     1       3.342   2.399  -0.290  1.00  0.00           H  
HETATM   43  H10 UNL     1       4.384   3.737   1.525  1.00  0.00           H  
HETATM   44  H11 UNL     1       4.107   0.458   4.232  1.00  0.00           H  
HETATM   45  H12 UNL     1       3.087  -0.845   2.450  1.00  0.00           H  
HETATM   46  H13 UNL     1       5.135  -0.282   0.089  1.00  0.00           H  
HETATM   47  H14 UNL     1       6.557  -1.717  -1.331  1.00  0.00           H  
HETATM   48  H15 UNL     1       5.514  -3.180  -2.999  1.00  0.00           H  
HETATM   49  H16 UNL     1       3.070  -3.211  -3.248  1.00  0.00           H  
HETATM   50  H17 UNL     1      -1.275  -1.682  -2.015  1.00  0.00           H  
HETATM   51  H18 UNL     1      -3.542   0.583  -0.132  1.00  0.00           H  
HETATM   52  H19 UNL     1      -5.116   0.439  -1.987  1.00  0.00           H  
HETATM   53  H20 UNL     1      -6.615  -1.106  -3.244  1.00  0.00           H  
HETATM   54  H21 UNL     1      -4.235  -4.383  -2.102  1.00  0.00           H  
HETATM   55  H22 UNL     1      -2.767  -2.902  -0.842  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    4   37
CONECT    3   38   39   40
CONECT    4    5    5
CONECT    5    6   25
CONECT    6    7    7   41
CONECT    7    8   23
CONECT    8    9   16
CONECT    9   10   10   15
CONECT   10   11   42
CONECT   11   12   12   43
CONECT   12   13   14
CONECT   14   15   15   44
CONECT   15   45
CONECT   16   17   17   21
CONECT   17   18   46
CONECT   18   19   19   47
CONECT   19   20   48
CONECT   20   21   21   49
CONECT   21   22
CONECT   22   23   23
CONECT   23   24
CONECT   24   25   25   50
CONECT   25   26
CONECT   26   27   51
CONECT   27   28   28   33
CONECT   28   29   52
CONECT   29   30   30   53
CONECT   30   31   32
CONECT   32   33   33   54
CONECT   33   55
END

HMDB0014983
     RDKit          3D
Clofazimine
 55 59  0  0  0  0  0  0  0  0999 V2000
   -2.2574    2.4931    3.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.9168    1.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548    3.1530    1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857    1.3315    1.2515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.5838    0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4191    0.6026    0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1993   -0.1808   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469   -0.1555   -0.0017 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.6943    0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186    1.9977    0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    2.7200    1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122    2.2018    2.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0448    3.1839    4.2028 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9478    0.9003    3.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701    0.1741    2.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2727   -0.9546   -0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6571   -0.9202   -0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4649   -1.7162   -1.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -2.5499   -2.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5061   -2.5597   -2.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6731   -1.7804   -1.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3349   -1.8155   -1.8967 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307   -1.0337   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -1.0462   -1.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045   -0.2432   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270   -0.1943   -0.5995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8175   -1.0949   -1.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9346   -0.6368   -2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7588   -1.4884   -2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5053   -2.8390   -2.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5714   -3.9362   -3.6377 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -3.3150   -2.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -2.4424   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    2.8350    3.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059    1.6637    3.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249    3.2678    2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    1.3167    2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    3.9592    1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1709    3.4311    1.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0871    2.9317   -0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049    1.2371    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3416    2.3986   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3841    3.7366    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1068    0.4575    4.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870   -0.8447    2.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355   -0.2821    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5573   -1.7165   -1.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145   -3.1802   -2.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703   -3.2107   -3.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750   -1.6816   -2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5419    0.5828   -0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1158    0.4387   -1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6148   -1.1063   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -4.3832   -2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7674   -2.9015   -0.8421 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  3
  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

View in JSmol View Stereo Labels

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 Molecular Weight

473.396

Monoisotopic Molecular Weight

472.122152138

IUPAC Name

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

Traditional Name

clofazimina

CAS Registry Number

2030-63-9

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

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 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014983)
Membrane (HMDB: HMDB0014983)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 212 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0015 g/L	Not Available
LogP	7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	211.563	30932474
DeepCCS	[M-H]-	209.168	30932474
DeepCCS	[M-2H]-	242.051	30932474
DeepCCS	[M+Na]+	217.476	30932474
AllCCS	[M+H]+	211.1	32859911
AllCCS	[M+H-H2O]+	209.1	32859911
AllCCS	[M+NH4]+	212.9	32859911
AllCCS	[M+Na]+	213.4	32859911
AllCCS	[M-H]-	172.1	32859911
AllCCS	[M+Na-2H]-	170.6	32859911
AllCCS	[M+HCOO]-	169.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clofazimine	CC(C)N=C1C=C2N(C3=CC=C(Cl)C=C3)C3=C(C=CC=C3)N=C2C=C1NC1=CC=C(Cl)C=C1	5521.1	Standard polar	33892256
Clofazimine	CC(C)N=C1C=C2N(C3=CC=C(Cl)C=C3)C3=C(C=CC=C3)N=C2C=C1NC1=CC=C(Cl)C=C1	3985.4	Standard non polar	33892256
Clofazimine	CC(C)N=C1C=C2N(C3=CC=C(Cl)C=C3)C3=C(C=CC=C3)N=C2C=C1NC1=CC=C(Cl)C=C1	4063.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Clofazimine,1TMS,isomer #1	CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C2=CC=C(Cl)C=C2)C=C1N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	3958.4	Semi standard non polar	33892256
Clofazimine,1TMS,isomer #1	CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C2=CC=C(Cl)C=C2)C=C1N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	3544.1	Standard non polar	33892256
Clofazimine,1TMS,isomer #1	CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C2=CC=C(Cl)C=C2)C=C1N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	5060.6	Standard polar	33892256
Clofazimine,1TBDMS,isomer #1	CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C2=CC=C(Cl)C=C2)C=C1N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	4104.5	Semi standard non polar	33892256
Clofazimine,1TBDMS,isomer #1	CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C2=CC=C(Cl)C=C2)C=C1N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3730.4	Standard non polar	33892256
Clofazimine,1TBDMS,isomer #1	CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C2=CC=C(Cl)C=C2)C=C1N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	5051.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clofazimine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-2012900000-925bda9ffd357867fda8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clofazimine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofazimine LC-ESI-qTof , Positive-QTOF	splash10-0zfr-0112112900-e3bfb9c4af77d4fe2af5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofazimine LC-ESI-qTof , Positive-QTOF	splash10-0f6t-2931000000-abbbe8c79a3a4d2e2a98	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofazimine , positive-QTOF	splash10-00fr-0000900000-e6674066d4ff0d54220f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofazimine , positive-QTOF	splash10-00ai-0122900000-6ab122b0d69d3063d257	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofazimine 35V, Positive-QTOF	splash10-00di-0000900000-6208605751ff4198259d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 10V, Positive-QTOF	splash10-00dj-0004900000-53aaf2e9feab733f5696	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 20V, Positive-QTOF	splash10-0002-0009300000-4e81c003ff635d972452	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 40V, Positive-QTOF	splash10-000t-1009200000-1453a7404269fe261b3c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 10V, Negative-QTOF	splash10-00di-0000900000-a77f21de408c977df7c1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 20V, Negative-QTOF	splash10-00di-0000900000-6b7cc7e41f8ea912dd22	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 40V, Negative-QTOF	splash10-004r-1303900000-1f018805b2b835da809b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 10V, Positive-QTOF	splash10-00di-0000900000-4bc61438169d333cca7c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 20V, Positive-QTOF	splash10-00di-0000900000-f04a0f2b905ba555c653	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 40V, Positive-QTOF	splash10-001j-0009600000-38a02d9b4caf79a840c7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 10V, Negative-QTOF	splash10-00di-0000900000-fa1ca7afb7582d14c164	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 20V, Negative-QTOF	splash10-00fr-0000900000-74b5c4b76177eb417437	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofazimine 40V, Negative-QTOF	splash10-001i-8014900000-27f589888478cc331350	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00845	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00845	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00845

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21159573

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

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)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]

Showing metabocard for Clofazimine (HMDB0014983)

MOL for HMDB0014983 (Clofazimine)

3D MOL for HMDB0014983 (Clofazimine)

3D SDF for HMDB0014983 (Clofazimine)

3D-SDF for HMDB0014983 (Clofazimine)

PDB for HMDB0014983 (Clofazimine)

3D PDB for HMDB0014983 (Clofazimine)

SMILES for HMDB0014983 (Clofazimine)

INCHI for HMDB0014983 (Clofazimine)

Structure for HMDB0014983 (Clofazimine)

3D Structure for HMDB0014983 (Clofazimine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References