((rac-exo)-7-Oxabicyclo[2.2.1]heptan-2-yl)(4-((4-(7-ethylimidazo-[1,2-a]pyridin-8-yl)-1,4-diazepan-1-yl)methyl)piperidin-1-yl)-methanone

ID: ALA4072602

PubChem CID: 137639002

Max Phase: Preclinical

Molecular Formula: C27H39N5O2

Molecular Weight: 465.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccn2ccnc2c1N1CCCN(CC2CCN(C(=O)[C@H]3C[C@@H]4CC[C@H]3O4)CC2)CC1

Standard InChI:  InChI=1S/C27H39N5O2/c1-2-21-8-14-31-15-9-28-26(31)25(21)30-11-3-10-29(16-17-30)19-20-6-12-32(13-7-20)27(33)23-18-22-4-5-24(23)34-22/h8-9,14-15,20,22-24H,2-7,10-13,16-19H2,1H3/t22-,23-,24+/m0/s1

Standard InChI Key:  ZUCRVTBTGIZZTG-KMDXXIMOSA-N

Molfile:  

     RDKit          2D

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   10.7913   -8.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4973   -9.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2002   -8.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1980   -7.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5406   -7.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.2953   -9.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.2041   -5.7061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1902   -4.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9471   -4.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5799   -7.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0796   -7.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0795   -6.5795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6655   -7.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548   -7.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3720   -8.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8697   -8.1810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3961   -7.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6655   -6.5793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6589   -9.8465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 21 22  1  0
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 11 16  1  0
  7  8  1  0
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  1 25  1  0
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 27 25  1  1
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 28 35  1  1
 31 36  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4072602

   ---

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 465.64

Molecular Weight (Monoisotopic): 465.3104

AlogP: 3.21

#Rotatable Bonds: 5

Polar Surface Area: 53.32

Molecular Species: BASE

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.39

CX LogP: 2.10

CX LogD: 0.09

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.68

Np Likeness Score: -1.00

References

1. Menhaji-Klotz E, Hesp KD, Londregan AT, Kalgutkar AS, Piotrowski DW, Boehm M, Song K, Ryder T, Beaumont K, Jones RM, Atkinson K, Brown JA, Litchfield J, Xiao J, Canterbury DP, Burford K, Thuma BA, Limberakis C, Jiao W, Bagley SW, Agarwal S, Crowell D, Pazdziorko S, Ward J, Price DA, Clerin V..  (2018)  Discovery of a Novel Small-Molecule Modulator of C-X-C Chemokine Receptor Type 7 as a Treatment for Cardiac Fibrosis.,  61  (8): [PMID:29627981] [10.1021/acs.jmedchem.8b00190]

2. Menhaji-Klotz E, Hesp KD, Londregan AT, Kalgutkar AS, Piotrowski DW, Boehm M, Song K, Ryder T, Beaumont K, Jones RM, Atkinson K, Brown JA, Litchfield J, Xiao J, Canterbury DP, Burford K, Thuma BA, Limberakis C, Jiao W, Bagley SW, Agarwal S, Crowell D, Pazdziorko S, Ward J, Price DA, Clerin V..  (2018)  Discovery of a Novel Small-Molecule Modulator of C-X-C Chemokine Receptor Type 7 as a Treatment for Cardiac Fibrosis.,  61  (8): [PMID:29627981] [10.1021/acs.jmedchem.8b00190]

3. Aspnes GE, Menhaji-Klotz E, Boehm M, Londregan AT, Lee ECY, Limberakis C, Coffey SB, Brown JA, Jones RM, Hesp KD..  (2021)  Discovery and evaluation of non-basic small molecule modulators of the atypical chemokine receptor CXCR7.,  50  [PMID:34400299] [10.1016/j.bmcl.2021.128320]

4. Richard-Bildstein, Sylvia and 8 more authors.  2020-12-24  Discovery of the Potent, Selective, Orally Available CXCR7 Antagonist ACT-1004-1239.  [PMID:33314938]

Source

Source(1):

• Scientific Literature