5-(2,3,7,8,9,9a-hexahydro-1H-phenalene-5-carboxamido)picolinic acid

ID: ALA2398384

PubChem CID: 58420584

Max Phase: Preclinical

Molecular Formula: C20H20N2O3

Molecular Weight: 336.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(C(=O)O)nc1)c1cc2c3c(c1)CCCC3CCC2

Standard InChI:  InChI=1S/C20H20N2O3/c23-19(22-16-7-8-17(20(24)25)21-11-16)15-9-13-5-1-3-12-4-2-6-14(10-15)18(12)13/h7-12H,1-6H2,(H,22,23)(H,24,25)

Standard InChI Key:  JDZFVFXEVBSKAV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   14.7053  -22.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7053  -22.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4106  -21.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4086  -23.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4023  -24.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1016  -24.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8088  -24.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1159  -22.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1143  -22.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8185  -23.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5248  -22.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5224  -22.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8176  -21.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2288  -21.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9378  -22.0940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6442  -21.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3546  -22.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0606  -21.6817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0584  -20.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3444  -20.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6414  -20.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7621  -20.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4770  -20.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7599  -19.6404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2262  -20.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  8  3  1  0
  9  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 10  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  1  0
 22 24  2  0
 19 22  1  0
 14 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2398384

   5-(5,6,6a,7,8,9-hexahydro-4H-phenalene-2-carbonylamino)pyridine-2-carboxylic acid

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: 336.39

Molecular Weight (Monoisotopic): 336.1474

AlogP: 3.79

#Rotatable Bonds: 3

Polar Surface Area: 79.29

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.07

CX Basic pKa: 5.14

CX LogP: 2.91

CX LogD: 0.92

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.89

Np Likeness Score: -0.78

References

1. Amano Y, Noguchi M, Nakagomi M, Muratake H, Fukasawa H, Shudo K..  (2013)  Design, synthesis and evaluation of retinoids with novel bulky hydrophobic partial structures.,  21  (14): [PMID:23685180] [10.1016/j.bmc.2013.04.053]

Source

Source(1):

• Scientific Literature