NP-MRD: Showing NP-Card for halofuginone (NP0307973)

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Record Information

Version

2.0

Created at

2022-09-11 01:27:50 UTC

Updated at

2022-09-11 01:27:50 UTC

NP-MRD ID

NP0307973

Secondary Accession Numbers

None

Natural Product Identification

Common Name

halofuginone

Description

Halofuginone 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. Inhibition of prolyl tRNA charging leads to the accumulation of uncharged prolyl tRNAs, which serve as a signal to initiate the amino acid starvation response, which in turn exerts anti-inflammatory and anti-fibrotic effects. Halofuginone is a drug which is used for the treatment of scleroderma, cancer, and restenosis. Halofuginone is a very strong basic compound (based on its pKa). Halofuginone therefore has potential for the treatment of autoimmune disorders. Collgard Biopharmaceuticals is developing halofuginone for the treatment of scleroderma and it has received orphan drug designation from the U.S. Food and Drug Administration. It is a synthetic halogenated derivative of febrifugine, a natural quinazolinone alkaloid which can be found in the Chinese herb Dichroa febrifuga (Chang Shan). Halofuginone is also an inhibitor of collagen type I gene expression and as a consequence it may inhibit tumor cell growth. Halofuginone exerts its effects by acting as a high affinity inhibitor of the enzyme glutamyl-prolyl tRNA synthetase. Halofuginone inhibits the development of T helper 17 cells, immune cells that play an important role in autoimmune disease, but it does not affect other kinds of T cells which are involved in normal immune function. halofuginone is found in Hydrangea febrifuga. Halofuginone is a coccidiostat used in veterinary medicine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041405112D          

 26 28  0  0  1  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  2  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  1  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
    6.4302    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 H   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  6  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
 15 23  1  1  0  0  0
 24 16  2  0  0  0  0
 14 25  1  1  0  0  0
 15 26  1  6  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.5062    1.4273   -1.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430    0.5441   -0.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185    0.6846    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4244   -0.3688    0.2614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1288   -0.4138    1.5100 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717    0.5507    1.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7513    1.0848    0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7580   -0.0488   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3034   -0.2950   -0.9400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2757   -1.4887   -1.6994 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -0.5984   -1.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7301   -0.4880   -0.3981 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8213   -0.9487    0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912   -0.8968    1.5543 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1153   -0.3816    0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -0.3313    1.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4068    0.1967    1.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1079    0.2984    1.9183 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.2801    0.6578   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6649    1.3339   -1.1008 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0749    0.6077   -0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814    0.0753   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870    0.0259   -1.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6482    0.4364   -2.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939    0.4787    1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371    1.7012    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692   -1.3539    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -1.3936    1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0130    0.0243    2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8701    1.3772    2.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8067    1.4283    0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2032    1.9686    0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3335    0.2804   -1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1346   -0.9606   -0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881    0.5101   -1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558   -2.2484   -1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848   -0.8053   -2.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -1.5777   -0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -1.3642    1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -0.6908    2.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9622    0.9618   -1.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 22  2  0
 22 21  1  0
 21 19  2  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 16  2  0
 22 23  1  0
 23 24  2  0
  4  9  1  0
 23 12  1  0
 16 15  1  0
  9 35  1  6
 10 36  1  0
  8 33  1  0
  8 34  1  0
  7 31  1  0
  7 32  1  0
  6 29  1  0
  6 30  1  0
  5 28  1  0
  4 27  1  6
  3 25  1  0
  3 26  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 21 41  1  0
 16 40  1  0
M  END


  Mrv0541 05041405112D          

 26 28  0  0  1  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  2  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  1  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
    6.4302    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 H   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  6  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
 15 23  1  1  0  0  0
 24 16  2  0  0  0  0
 14 25  1  1  0  0  0
 15 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0307973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(O)CCCN[C@]1([H])CC(=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/t14-,15+/m1/s1

> <INCHI_KEY>
LVASCWIMLIKXLA-CABCVRRESA-N

> <FORMULA>
C16H17BrClN3O3

> <MOLECULAR_WEIGHT>
414.681

> <EXACT_MASS>
413.014181779

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.169976931113794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-bromo-6-chloro-3-{3-[(2R,3S)-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-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+0
HETATM   18 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   19  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+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   25                                             
CONECT   15    2   14   23   26                                             
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                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Rel-halofuginone	ChEMBL
7-bromo-6-Chlorofebrifugine	MeSH
Stenorol	MeSH
Halofunginone	MeSH

Chemical Formula

C₁₆H₁₇BrClN₃O₃

Average Mass

414.6810 Da

Monoisotopic Mass

413.01418 Da

IUPAC Name

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

Traditional Name

7-bromo-6-chloro-3-{3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4-one

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)CCCN[C@]1([H])CC(=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/t14-,15+/m1/s1

InChI Key

LVASCWIMLIKXLA-CABCVRRESA-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
Dichroa febrifuga	LOTUS Database	35616633

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

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	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	37.17 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

External Links

HMDB ID

Not Available

DrugBank ID

DB04866

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Halofuginone

METLIN ID

Not Available

PubChem Compound

456390

PDB ID

HFG

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for halofuginone (NP0307973)

MOL for NP0307973 (halofuginone)

3D MOL for NP0307973 (halofuginone)

3D SDF for NP0307973 (halofuginone)

3D-SDF for NP0307973 (halofuginone)

PDB for NP0307973 (halofuginone)

3D PDB for NP0307973 (halofuginone)

SMILES for NP0307973 (halofuginone)

INCHI for NP0307973 (halofuginone)

Structure for NP0307973 (halofuginone)

3D Structure for NP0307973 (halofuginone)