Chemical Components in the PDB

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HFG : Summary

Code

HFG

One-letter code

X

Molecule name

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

Synonyms

Halofuginone

Systematic names

ProgramVersionName
ACDLabs 12.01 7-bromo-6-chloro-3-{3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
OpenEye OEToolkits 1.7.6 7-bromanyl-6-chloranyl-3-[2-oxidanylidene-3-[(2R,3S)-3-oxidanylpiperidin-2-yl]propyl]quinazolin-4-one

Formula

C16 H17 Br Cl N3 O3

Formal charge

0

Molecular weight

414.681 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 Brc3c(Cl)cc1c(N=CN(C1=O)CC(=O)CC2NCCCC2O)c3
SMILES CACTVS 3.370 O[CH]1CCCN[CH]1CC(=O)CN2C=Nc3cc(Br)c(Cl)cc3C2=O
SMILES OpenEye OEToolkits 1.7.6 c1c2c(cc(c1Cl)Br)N=CN(C2=O)CC(=O)CC3C(CCCN3)O
Canonical SMILES CACTVS 3.370 O[C@H]1CCCN[C@@H]1CC(=O)CN2C=Nc3cc(Br)c(Cl)cc3C2=O
Canonical SMILES OpenEye OEToolkits 1.7.6 c1c2c(cc(c1Cl)Br)N=CN(C2=O)CC(=O)C[C@@H]3[C@H](CCCN3)O

IUPAC InChI

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

IUPAC InChI key

LVASCWIMLIKXLA-CABCVRRESA-N
HFG

wwPDB Information

Atom count

41 (24 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2012-11-09

Last modified at

2013-02-07

Status

Released

Obsoleted

Not Assigned



HFG : Atoms of Molecule

Total Number of Atoms: 41
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 BR1 BR BR1 N N N 0 -5.692 0.059 1.002
2 C1' C C1' N N N 0 2.114 1.558 -1.36
3 C10 C C10 N Y N 0 -1.381 0.266 -0.763
4 C2 C C2 N N N 0 0.249 2.302 0.03
5 C2' C C2' R N N 0 5.268 -0.035 0.295
6 C21 C C21 N N N 0 3.061 0.807 -0.461
7 C3' C C3' N N N 0 4.538 0.8 -0.759
8 C39 C C39 S N N 0 6.778 0.06 0.065
9 C4 C C4 N N N 0 -0.014 0.371 -1.294
10 C4' C C4' N N N 0 7.503 -0.792 1.11
11 C5 C C5 N Y N 0 -2.243 -0.761 -1.143
12 C5' C C5' N N N 0 7.006 -2.237 1.013
13 C6 C C6 N Y N 0 -3.515 -0.811 -0.614
14 C6' C C6' N N N 0 5.49 -2.266 1.215
15 C7 C C7 N Y N 0 -3.941 0.153 0.293
16 C8 C C8 N Y N 0 -3.104 1.176 0.68
17 C9 C C9 N Y N 0 -1.812 1.248 0.157
18 CL1 CL CL1 N N N 0 -4.593 -2.089 -1.084
19 H1 H H1 N N N 0 4.707 0.367 -1.745
20 H10 H H10 N N N 0 7.294 -0.402 2.107
21 H11 H H11 N N N 0 8.576 -0.762 0.925
22 H12 H H12 N N N 0 7.017 -0.306 -0.933
23 H13 H H13 N N N 0 8.143 1.556 0.053
24 H14 H H14 N N N 0 2.382 2.614 -1.369
25 H15 H H15 N N N 0 2.18 1.158 -2.372
26 H16 H H16 N N N 0 -1.916 -1.512 -1.847
27 H17 H H17 N N N 0 0.888 3.11 0.352
28 H18 H H18 N N N 0 -3.447 1.919 1.385
29 H2 H H2 N N N 0 4.917 1.821 -0.741
30 H3 H H3 N N N 0 5.027 0.345 1.288
31 H4 H H4 N N N 0 5.019 -1.8 -0.734
32 H6 H H6 N N N 0 5.248 -1.876 2.204
33 H7 H H7 N N N 0 5.131 -3.292 1.132
34 H8 H H8 N N N 0 7.488 -2.841 1.782
35 H9 H H9 N N N 0 7.25 -2.64 0.029
36 N1 N N1 N N N 0 -0.953 2.235 0.516
37 N1' N N1' N N N 0 4.842 -1.436 0.191
38 N3 N N3 N N N 0 0.744 1.406 -0.863
39 O11 O O11 N N N 0 0.418 -0.442 -2.09
40 O4' O O4' N N N 0 2.636 0.206 0.497
41 O7' O O7' N N N 0 7.194 1.421 0.187



HFG : Chemical Bonds

Total Number of Bonds: 43
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 CL1 C6 CL C sing 1.74 N N
2 C6 C5 C C doub 1.38 N Y
3 C6 C7 C C sing 1.39 N Y
4 BR1 C7 BR C sing 1.89 N N
5 C5 C10 C C sing 1.39 N Y
6 C7 C8 C C doub 1.38 N Y
7 O11 C4 O C doub 1.22 N N
8 C10 C4 C C sing 1.47 N N
9 C10 C9 C C doub 1.41 N Y
10 C8 C9 C C sing 1.4 N Y
11 C4 N3 C N sing 1.35 N N
12 C9 N1 C N sing 1.36 N N
13 N1' C6' N C sing 1.47 N N
14 N1' C2' N C sing 1.47 N N
15 C6' C5' C C sing 1.53 N N
16 O4' C21 O C doub 1.21 N N
17 N3 C1' N C sing 1.47 N N
18 N3 C2 N C sing 1.36 N N
19 N1 C2 N C doub 1.3 N N
20 C21 C3' C C sing 1.51 N N
21 C21 C1' C C sing 1.51 N N
22 C3' C2' C C sing 1.53 N N
23 C2' C39 C C sing 1.53 N N
24 C5' C4' C C sing 1.53 N N
25 C39 C4' C C sing 1.53 N N
26 C39 O7' C O sing 1.43 N N
27 C3' H1 C H sing 1.09 N N
28 C3' H2 C H sing 1.09 N N
29 C2' H3 C H sing 1.09 N N
30 N1' H4 N H sing 1.01 N N
31 C6' H6 C H sing 1.09 N N
32 C6' H7 C H sing 1.09 N N
33 C5' H8 C H sing 1.09 N N
34 C5' H9 C H sing 1.09 N N
35 C4' H10 C H sing 1.09 N N
36 C4' H11 C H sing 1.09 N N
37 C39 H12 C H sing 1.09 N N
38 O7' H13 O H sing 0.97 N N
39 C1' H14 C H sing 1.09 N N
40 C1' H15 C H sing 1.09 N N
41 C5 H16 C H sing 1.08 N N
42 C2 H17 C H sing 1.08 N N
43 C8 H18 C H sing 1.08 N N



HFG : Used in PDB Entries

Total Number of PDB Entries: 6
Ligand Code PDB Entry ID Type Total Distinct
HFG 4hvc Open in New Window Bound ligand 2 1
HFG 4k88 Open in New Window Bound ligand 1 1
HFG 4olf Open in New Window Bound ligand 1 1
HFG 4q15 Open in New Window Bound ligand 2 1
HFG 4ydq Open in New Window Bound ligand 2 1
HFG 5f9z Open in New Window Bound ligand 2 1