exo-2-(6-{[(6-Fluoroquinolin-2-yl)methyl]amino}bicyclo[3.1.0]hex-3-yl)-N-hydroxypyrimidine-5-carboxamide

ID: ALA1801250

Cas Number: 1256448-47-1

PubChem CID: 49857317

Product Number: C608546, Order Now?

Max Phase: Phase

Molecular Formula: C20H19FN6O2

Molecular Weight: 394.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Chr 3996 | Hdac inhibitor chr-3996 | Nanatinostat | CHR-3996 | VRX-3996 | Nanatinostat|CHR-3996|Hdac inhibitor CHR-3996|1256448-47-1|Nanatinostat [USAN]|VRX-3996|YTL7A418KQ|CHR 3996|UNII-YTL7A418KQ|CHEMBL1801250|WHO 10911|Nanatinostat (USAN)|2-((1alpha,5alpha,6alpha)-6-(((6-Fluoro-2-quinolinyl)methyl)amino)-3-azabicyclo(3.1.0)hex-3-yl)-N-hydroxy-5-pyrimidinecarboxamide|2-[(1S,5R)-6-[(6-fluoroquinolin-2-yl)methylamino]-3-azabicyclo[3.1.0]hexan-3-yl]-N-hydroxypyrimidine-5-carboxamide|5-PyrimidinecShow More⌵

Canonical SMILES:  O=C(NO)c1cnc(N2C[C@@H]3[C@H](C2)[C@H]3NCc2ccc3cc(F)ccc3n2)nc1

Standard InChI:  InChI=1S/C20H19FN6O2/c21-13-2-4-17-11(5-13)1-3-14(25-17)8-22-18-15-9-27(10-16(15)18)20-23-6-12(7-24-20)19(28)26-29/h1-7,15-16,18,22,29H,8-10H2,(H,26,28)/t15-,16+,18+

Standard InChI Key:  QRGHOAATPOLDPF-VQFNDLOPSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   -4.3442   -0.5913    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297   -0.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297    0.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9152    1.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9152   -0.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -0.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008    0.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4863    1.0588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4863   -0.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718   -0.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718    0.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574    1.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6571    0.6463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2172    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3567    2.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0242    1.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1104    2.0128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1372    2.2202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3249    0.2029    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8354    2.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138    3.2312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604    2.0128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5172    3.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2639    2.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423    3.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222    3.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9438    4.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6472    3.3422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3271    3.8095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  5  6  1  0
  6  7  2  0
  4  7  1  0
  2  5  2  0
  4  3  2  0
  9 10  2  0
 10 11  1  0
  8 11  2  0
  6  9  1  0
  8  7  1  0
 12 13  1  0
 12 11  1  0
 14 13  1  6
 14 15  1  0
 14 16  1  0
 15 16  1  0
 15 17  1  0
 16 18  1  0
 17 19  1  0
 19 18  1  0
 15 20  1  6
 16 21  1  6
 19 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  2  0
 24 26  1  0
 25 27  1  0
 27 26  2  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1801250

   CHR-3996

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.41

Molecular Weight (Monoisotopic): 394.1554

AlogP: 1.51

#Rotatable Bonds: 5

Polar Surface Area: 103.27

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.89

CX Basic pKa: 8.24

CX LogP: 0.50

CX LogD: -0.02

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.25

References

1. Moffat D, Patel S, Day F, Belfield A, Donald A, Rowlands M, Wibawa J, Brotherton D, Stimson L, Clark V, Owen J, Bawden L, Box G, Bone E, Mortenson P, Hardcastle A, van Meurs S, Eccles S, Raynaud F, Aherne W..  (2010)  Discovery of 2-(6-{[(6-fluoroquinolin-2-yl)methyl]amino}bicyclo[3.1.0]hex-3-yl)-N-hydroxypyrimidine-5-carboxamide (CHR-3996), a class I selective orally active histone deacetylase inhibitor.,  53  (24): [PMID:21080647] [10.1021/jm101177s]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names