5-(4-(4-(3,3-dimethylbutanoyl)-3-hydroxy-2-methylphenoxy)butoxy)nicotinic acid

ID: ALA4858387

PubChem CID: 164610947

Max Phase: Preclinical

Molecular Formula: C23H29NO6

Molecular Weight: 415.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(OCCCCOc2cncc(C(=O)O)c2)ccc(C(=O)CC(C)(C)C)c1O

Standard InChI:  InChI=1S/C23H29NO6/c1-15-20(8-7-18(21(15)26)19(25)12-23(2,3)4)30-10-6-5-9-29-17-11-16(22(27)28)13-24-14-17/h7-8,11,13-14,26H,5-6,9-10,12H2,1-4H3,(H,27,28)

Standard InChI Key:  CODNVLPFPDYVJB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.6158   -2.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6147   -3.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3227   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0324   -3.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0295   -2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3209   -2.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9080   -2.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3185   -1.3204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7357   -2.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4449   -2.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7326   -1.3144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1511   -2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8603   -2.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1480   -1.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8559   -1.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9066   -3.7740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1992   -3.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4912   -3.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7838   -3.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0758   -3.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3684   -3.3626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6604   -3.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9556   -3.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2480   -3.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2470   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9593   -4.9943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6640   -4.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5409   -3.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5419   -2.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8326   -3.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 24 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4858387

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 415.49

Molecular Weight (Monoisotopic): 415.1995

AlogP: 4.65

#Rotatable Bonds: 10

Polar Surface Area: 105.95

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: 2.62

CX LogP: 4.22

CX LogD: 1.32

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -0.29

References

1. Yamada Y, Gilliland K, Xiang Z, Haymer D, Crocker KE, Loch MT, Schulte ML, Rodriguez AL, Niswender CM, Jeffrey Conn P, Lindsley CW, Melancon BJ..  (2021)  Positive allosteric modulators (PAMs) of the group II metabotropic glutamate receptors: Design, synthesis, and evaluation as ex-vivo tool compounds.,  50  [PMID:34461178] [10.1016/j.bmcl.2021.128342]

Source

Source(1):

• Scientific Literature