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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:26 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031784

Secondary Accession Numbers

HMDB31784

Metabolite Identification

Common Name

Halofuginone

Description

Veterinary antiprotozoal agent. Poultry feed additive for prevention of coccidiosis. Halofuginone is a coccidiostat used in veterinary medicine. It is derived from dichrorine, a kind of alkaloids which can be found in the Chinese herb Chang Shan (Dichroa febrifuga). Halofuginone, a fully synthetic small molecule, is a potent and selective regulator of stromal cell activation, cell migration and Collagen type I synthesis, a process that has been identified as a 'master switch' in the body's tissue repair process

Structure

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

HMDB0031784
     RDKit          3D
Halofuginone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.0828   -1.4300   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -1.1476   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1805   -0.0600    0.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6122   -0.3528    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202    0.7811    1.7999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5836    1.8010    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9448    1.3124    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8568   -0.1209   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4103   -0.6039   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5329   -1.9875   -0.4608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6827   -1.8702    0.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234   -1.3102   -0.1365 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -1.7290   -1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849   -1.2387   -1.8067 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2829   -0.2987   -1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4785    0.1944   -1.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736    1.1518   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204    1.8734   -1.6008 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.6572    1.5827    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502    2.7957    1.1501 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4771    1.0936    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7690    0.1336    0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -0.3781    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708    0.0627    1.6765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    0.9114    0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640    0.0980    1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -1.2704    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3785    1.1439    2.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8892    1.9378    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993    2.7655    1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3276    1.9473   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6503    1.4182    1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -0.7446    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3008   -0.2111   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0031   -0.1186   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -2.0967   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -1.8099    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6235   -2.9803    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491   -2.4922   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8552   -0.1723   -2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    1.4191    1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  9  4  1  0
 23 12  1  0
 22 15  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 21 41  1  0
M  END

  Mrv0541 05061306072D          

 24 26  0  0  0  0            999 V2000
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    5.0013   -0.4125    0.0000 C   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
    5.7158    0.0000    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
    1.4289    0.8250    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   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
    0.7145    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 N   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
    4.2868    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  5  2  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  2  0  0  0  0
 14  4  1  0  0  0  0
 15  2  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19  3  1  0  0  0  0
 19 14  1  0  0  0  0
 20  8  2  0  0  0  0
 20 13  1  0  0  0  0
 21  7  1  0  0  0  0
 21  8  1  0  0  0  0
 21 16  1  0  0  0  0
 22  9  2  0  0  0  0
 23 15  1  0  0  0  0
 24 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031784

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CCCNC1CC(=O)CN1C=NC2=C(C=C(Cl)C(Br)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2

> <INCHI_KEY>
LVASCWIMLIKXLA-UHFFFAOYSA-N

> <FORMULA>
C16H17BrClN3O3

> <MOLECULAR_WEIGHT>
414.681

> <EXACT_MASS>
413.014181779

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.21088873951052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.7095168736666668

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.93551851593693

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.481944824501802

> <JCHEM_PKA_STRONGEST_BASIC>
9.284795756086915

> <JCHEM_POLAR_SURFACE_AREA>
82

> <JCHEM_REFRACTIVITY>
95.8668

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]quinazolin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031784
     RDKit          3D
Halofuginone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.0828   -1.4300   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -1.1476   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1805   -0.0600    0.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6122   -0.3528    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202    0.7811    1.7999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5836    1.8010    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9448    1.3124    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8568   -0.1209   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4103   -0.6039   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5329   -1.9875   -0.4608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6827   -1.8702    0.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234   -1.3102   -0.1365 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -1.7290   -1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849   -1.2387   -1.8067 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2829   -0.2987   -1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4785    0.1944   -1.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736    1.1518   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204    1.8734   -1.6008 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.6572    1.5827    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502    2.7957    1.1501 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4771    1.0936    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7690    0.1336    0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -0.3781    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708    0.0627    1.6765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    0.9114    0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640    0.0980    1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -1.2704    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3785    1.1439    2.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8892    1.9378    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993    2.7655    1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3276    1.9473   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6503    1.4182    1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -0.7446    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3008   -0.2111   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0031   -0.1186   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -2.0967   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -1.8099    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6235   -2.9803    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491   -2.4922   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8552   -0.1723   -2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    1.4191    1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  9  4  1  0
 23 12  1  0
 22 15  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   0.000   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       1.334   2.310   0.000  0.00  0.00          Br+0
HETATM   18 Cl   UNK     0       1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   19  N   UNK     0      14.671  -0.770   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       6.668   2.310   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       8.002   0.000   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1   15                                                       
CONECT    3    1   19                                                       
CONECT    4    9   14                                                       
CONECT    5   10   12                                                       
CONECT    6   11   13                                                       
CONECT    7    9   21                                                       
CONECT    8   20   21                                                       
CONECT    9    4    7   22                                                  
CONECT   10    5   13   16                                                  
CONECT   11    6   12   17                                                  
CONECT   12    5   11   18                                                  
CONECT   13    6   10   20                                                  
CONECT   14    4   15   19                                                  
CONECT   15    2   14   23                                                  
CONECT   16   10   21   24                                                  
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19    3   14                                                       
CONECT   20    8   13                                                       
CONECT   21    7    8   16                                                  
CONECT   22    9                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0031784
HETATM    1  O1  UNL     1      -1.083  -1.430  -1.139  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.528  -1.148  -0.064  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.180  -0.060   0.713  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.612  -0.353   1.042  1.00  0.00           C  
HETATM    5  N1  UNL     1      -3.120   0.781   1.800  1.00  0.00           N  
HETATM    6  C4  UNL     1      -3.584   1.801   0.891  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.945   1.312   0.374  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.857  -0.121  -0.071  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.410  -0.604  -0.189  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.533  -1.988  -0.461  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.683  -1.870   0.365  1.00  0.00           C  
HETATM   12  N2  UNL     1       1.923  -1.310  -0.136  1.00  0.00           N  
HETATM   13  C9  UNL     1       2.439  -1.729  -1.323  1.00  0.00           C  
HETATM   14  N3  UNL     1       3.585  -1.239  -1.807  1.00  0.00           N  
HETATM   15  C10 UNL     1       4.283  -0.299  -1.132  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.479   0.194  -1.657  1.00  0.00           C  
HETATM   17  C12 UNL     1       6.174   1.152  -0.945  1.00  0.00           C  
HETATM   18 BR1  UNL     1       7.820   1.873  -1.601  1.00  0.00          BR  
HETATM   19  C13 UNL     1       5.657   1.583   0.259  1.00  0.00           C  
HETATM   20 CL1  UNL     1       6.550   2.796   1.150  1.00  0.00          CL  
HETATM   21  C14 UNL     1       4.477   1.094   0.774  1.00  0.00           C  
HETATM   22  C15 UNL     1       3.769   0.134   0.072  1.00  0.00           C  
HETATM   23  C16 UNL     1       2.577  -0.378   0.574  1.00  0.00           C  
HETATM   24  O3  UNL     1       2.171   0.063   1.677  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.117   0.911   0.169  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.564   0.098   1.634  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.687  -1.270   1.674  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.379   1.144   2.431  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.889   1.938   0.044  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.699   2.765   1.416  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.328   1.947  -0.427  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.650   1.418   1.240  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.421  -0.745   0.676  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.301  -0.211  -1.084  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.003  -0.119  -1.084  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.811  -2.097  -1.420  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.723  -1.810   1.495  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.623  -2.980   0.156  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.849  -2.492  -1.847  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.855  -0.172  -2.611  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.064   1.419   1.712  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   25   26
CONECT    4    5    9   27
CONECT    5    6   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   35
CONECT   10   36
CONECT   11   12   37   38
CONECT   12   13   23
CONECT   13   14   14   39
CONECT   14   15
CONECT   15   16   16   22
CONECT   16   17   40
CONECT   17   18   19   19
CONECT   19   20   21
CONECT   21   22   22   41
CONECT   22   23
CONECT   23   24   24
END

HMDB0031784
     RDKit          3D
Halofuginone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.0828   -1.4300   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282   -1.1476   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1805   -0.0600    0.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6122   -0.3528    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202    0.7811    1.7999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5836    1.8010    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9448    1.3124    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8568   -0.1209   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4103   -0.6039   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5329   -1.9875   -0.4608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6827   -1.8702    0.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234   -1.3102   -0.1365 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390   -1.7290   -1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849   -1.2387   -1.8067 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2829   -0.2987   -1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4785    0.1944   -1.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736    1.1518   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204    1.8734   -1.6008 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.6572    1.5827    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502    2.7957    1.1501 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4771    1.0936    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7690    0.1336    0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -0.3781    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708    0.0627    1.6765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    0.9114    0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640    0.0980    1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -1.2704    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3785    1.1439    2.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8892    1.9378    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993    2.7655    1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3276    1.9473   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6503    1.4182    1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214   -0.7446    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3008   -0.2111   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0031   -0.1186   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -2.0967   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -1.8099    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6235   -2.9803    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491   -2.4922   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8552   -0.1723   -2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    1.4191    1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  9  4  1  0
 23 12  1  0
 22 15  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone, 9ci	HMDB
C16H17BRCLN3O3	HMDB
Halofuginona	HMDB
Halofuginonum	HMDB
7-Bromo-6-chlorofebrifugine	HMDB
Stenorol	HMDB
Halofunginone	HMDB
Halofuginone	MeSH

Chemical Formula

C₁₆H₁₇BrClN₃O₃

Average Molecular Weight

414.681

Monoisotopic Molecular Weight

413.014181779

IUPAC Name

7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one

Traditional Name

7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]quinazolin-4-one

CAS Registry Number

55837-20-2

SMILES

OC1CCCNC1CC(=O)CN1C=NC2=C(C=C(Cl)C(Br)=C2)C1=O

InChI Identifier

InChI=1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2

InChI Key

LVASCWIMLIKXLA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolines

Alternative Parents

Substituents

Quinazoline
Pyrimidone
Aryl bromide
Aryl chloride
Aryl halide
Beta-aminoketone
Benzenoid
Pyrimidine
Piperidine
Heteroaromatic compound
1,2-aminoalcohol
Ketone
Lactam
Secondary alcohol
Secondary aliphatic amine
Azacycle
Secondary amine
Organobromide
Organohalogen compound
Amine
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031784)
Cytoplasm (HMDB: HMDB0031784)

Source

Exogenous

Exogenous (HMDB: HMDB0031784)

Food

Food (HMDB: HMDB0031784)

Endogenous

Endogenous (HMDB: HMDB0031784)

Process

Not Available

Role

Biological role

Anti-inflammatory (HMDB: HMDB0031784)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	1.38	ALOGPS
logP	1.71	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.87 m³·mol⁻¹	ChemAxon
Polarizability	36.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	179.617	30932474
DeepCCS	[M-H]-	177.259	30932474
DeepCCS	[M-2H]-	210.144	30932474
DeepCCS	[M+Na]+	185.915	30932474
AllCCS	[M+H]+	186.4	32859911
AllCCS	[M+H-H2O]+	183.7	32859911
AllCCS	[M+NH4]+	188.8	32859911
AllCCS	[M+Na]+	189.5	32859911
AllCCS	[M-H]-	185.1	32859911
AllCCS	[M+Na-2H]-	185.5	32859911
AllCCS	[M+HCOO]-	186.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Halofuginone	OC1CCCNC1CC(=O)CN1C=NC2=C(C=C(Cl)C(Br)=C2)C1=O	4006.9	Standard polar	33892256
Halofuginone	OC1CCCNC1CC(=O)CN1C=NC2=C(C=C(Cl)C(Br)=C2)C1=O	2820.0	Standard non polar	33892256
Halofuginone	OC1CCCNC1CC(=O)CN1C=NC2=C(C=C(Cl)C(Br)=C2)C1=O	3420.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Halofuginone,1TMS,isomer #1	C[Si](C)(C)OC1CCCNC1CC(=O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3324.0	Semi standard non polar	33892256
Halofuginone,1TMS,isomer #2	C[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1NCCCC1O	3456.6	Semi standard non polar	33892256
Halofuginone,1TMS,isomer #3	C[Si](C)(C)OC(=CC1NCCCC1O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3389.9	Semi standard non polar	33892256
Halofuginone,1TMS,isomer #4	C[Si](C)(C)N1CCCC(O)C1CC(=O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3339.1	Semi standard non polar	33892256
Halofuginone,2TMS,isomer #1	C[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1NCCCC1O[Si](C)(C)C	3333.0	Semi standard non polar	33892256
Halofuginone,2TMS,isomer #1	C[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1NCCCC1O[Si](C)(C)C	3164.8	Standard non polar	33892256
Halofuginone,2TMS,isomer #2	C[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3282.4	Semi standard non polar	33892256
Halofuginone,2TMS,isomer #2	C[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3173.4	Standard non polar	33892256
Halofuginone,2TMS,isomer #3	C[Si](C)(C)OC1CCCN([Si](C)(C)C)C1CC(=O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3246.7	Semi standard non polar	33892256
Halofuginone,2TMS,isomer #3	C[Si](C)(C)OC1CCCN([Si](C)(C)C)C1CC(=O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3282.5	Standard non polar	33892256
Halofuginone,2TMS,isomer #4	C[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C	3338.2	Semi standard non polar	33892256
Halofuginone,2TMS,isomer #4	C[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C	3340.0	Standard non polar	33892256
Halofuginone,2TMS,isomer #5	C[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3308.7	Semi standard non polar	33892256
Halofuginone,2TMS,isomer #5	C[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3312.3	Standard non polar	33892256
Halofuginone,3TMS,isomer #1	C[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C	3276.0	Semi standard non polar	33892256
Halofuginone,3TMS,isomer #1	C[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C	3319.4	Standard non polar	33892256
Halofuginone,3TMS,isomer #2	C[Si](C)(C)OC(=CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3270.3	Semi standard non polar	33892256
Halofuginone,3TMS,isomer #2	C[Si](C)(C)OC(=CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3300.2	Standard non polar	33892256
Halofuginone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCCNC1CC(=O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3536.2	Semi standard non polar	33892256
Halofuginone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1NCCCC1O	3676.1	Semi standard non polar	33892256
Halofuginone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3619.5	Semi standard non polar	33892256
Halofuginone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1CCCC(O)C1CC(=O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3599.6	Semi standard non polar	33892256
Halofuginone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1NCCCC1O[Si](C)(C)C(C)(C)C	3808.7	Semi standard non polar	33892256
Halofuginone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1NCCCC1O[Si](C)(C)C(C)(C)C	3577.2	Standard non polar	33892256
Halofuginone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C(C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3771.7	Semi standard non polar	33892256
Halofuginone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C(C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3585.4	Standard non polar	33892256
Halofuginone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1CCCN([Si](C)(C)C(C)(C)C)C1CC(=O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3729.3	Semi standard non polar	33892256
Halofuginone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1CCCN([Si](C)(C)C(C)(C)C)C1CC(=O)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3687.7	Standard non polar	33892256
Halofuginone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C(C)(C)C	3842.0	Semi standard non polar	33892256
Halofuginone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C(C)(C)C	3720.2	Standard non polar	33892256
Halofuginone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3795.0	Semi standard non polar	33892256
Halofuginone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3691.8	Standard non polar	33892256
Halofuginone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C	4022.4	Semi standard non polar	33892256
Halofuginone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O)CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C	3865.5	Standard non polar	33892256
Halofuginone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3984.5	Semi standard non polar	33892256
Halofuginone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC(Br)=C(Cl)C=C2C1=O	3848.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Halofuginone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9531000000-ad6d23d97b7b8b802456	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Halofuginone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9772100000-33f767c26405baf989d5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Halofuginone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Halofuginone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 10V, Positive-QTOF	splash10-01ot-0019400000-ef37bff5ad2e7944f658	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 20V, Positive-QTOF	splash10-0032-4229100000-9dcac476806bf59275f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 40V, Positive-QTOF	splash10-0a59-2091000000-5bf157bd94019fecfb6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 10V, Negative-QTOF	splash10-03di-0023900000-140a33008401d0012984	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 20V, Negative-QTOF	splash10-0bt9-5095200000-5d19f101c04a8000ea81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 40V, Negative-QTOF	splash10-056r-1190000000-45f00a76c454d6ef5d31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 10V, Positive-QTOF	splash10-0002-0009300000-7afba3c2c7d0c13e0159	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 20V, Positive-QTOF	splash10-022a-0149300000-66b7f003bd06aa717823	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 40V, Positive-QTOF	splash10-00ea-5093000000-0c47978e630a5c91d73e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 10V, Negative-QTOF	splash10-03dl-0046900000-b271a5f6055f2a12bc42	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 20V, Negative-QTOF	splash10-0006-0139000000-08906f28b7da88fd8c64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofuginone 40V, Negative-QTOF	splash10-0a4l-2190100000-7cf63cdf29574b0ee2a0	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008457

KNApSAcK ID

Not Available

Chemspider ID

56619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Halofuginone

METLIN ID

Not Available

PubChem Compound

62894

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Elkin M, Miao HQ, Nagler A, Aingorn E, Reich R, Hemo I, Dou HL, Pines M, Vlodavsky I: Halofuginone: a potent inhibitor of critical steps in angiogenesis progression. FASEB J. 2000 Dec;14(15):2477-85. [PubMed:11099465 ]
Karakoyun B, Yuksel M, Ercan F, Salva E, Isik I, Yegen BC: Halofuginone, a specific inhibitor of collagen type 1 synthesis, ameliorates oxidant colonic damage in rats with experimental colitis. Dig Dis Sci. 2010 Mar;55(3):607-16. doi: 10.1007/s10620-009-0798-0. Epub 2009 Apr 24. [PubMed:19390970 ]
McLaughlin NP, Evans P: Dihydroxylation of vinyl sulfones: stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone. J Org Chem. 2010 Jan 15;75(2):518-21. doi: 10.1021/jo902396m. [PubMed:20000346 ]
Nagler A, Katz A, Aingorn H, Miao HQ, Condiotti R, Genina O, Pines M, Vlodavsky I: Inhibition of glomerular mesangial cell proliferation and extracellular matrix deposition by halofuginone. Kidney Int. 1997 Dec;52(6):1561-9. [PubMed:9407501 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Collagen alpha-1(I) chain

General function:: Involved in extracellular matrix structural constituent
Specific function:: Type I collagen is a member of group I collagen (fibrillar forming collagen)
Gene Name:: COL1A1
Uniprot ID:: P02452
Molecular weight:: 138941.1

References

Elkin M, Miao HQ, Nagler A, Aingorn E, Reich R, Hemo I, Dou HL, Pines M, Vlodavsky I: Halofuginone: a potent inhibitor of critical steps in angiogenesis progression. FASEB J. 2000 Dec;14(15):2477-85. [PubMed:11099465 ]

Enzyme Details

2. 72 kDa type IV collagenase

General function:: Involved in metalloendopeptidase activity
Specific function:: PEX, the C-terminal non-catalytic fragment of MMP2, posseses anti-angiogenic and anti-tumor properties and inhibits cell migration and cell adhesion to FGF2 and vitronectin. Ligand for integrinv/beta3 on the surface of blood vessels
Gene Name:: MMP2
Uniprot ID:: P08253
Molecular weight:: 73881.7

References

Elkin M, Miao HQ, Nagler A, Aingorn E, Reich R, Hemo I, Dou HL, Pines M, Vlodavsky I: Halofuginone: a potent inhibitor of critical steps in angiogenesis progression. FASEB J. 2000 Dec;14(15):2477-85. [PubMed:11099465 ]

Showing metabocard for Halofuginone (HMDB0031784)

MOL for HMDB0031784 (Halofuginone)

3D MOL for HMDB0031784 (Halofuginone)

3D SDF for HMDB0031784 (Halofuginone)

3D-SDF for HMDB0031784 (Halofuginone)

PDB for HMDB0031784 (Halofuginone)

3D PDB for HMDB0031784 (Halofuginone)

SMILES for HMDB0031784 (Halofuginone)

INCHI for HMDB0031784 (Halofuginone)

Structure for HMDB0031784 (Halofuginone)

3D Structure for HMDB0031784 (Halofuginone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References