5-[(6a-Methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carbamoyl]pyridine-2-carboxylic acid

ID: ALA2398378

PubChem CID: 25189932

Max Phase: Preclinical

Molecular Formula: C21H22N2O3

Molecular Weight: 350.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12CCCc3cc(NC(=O)c4ccc(C(=O)O)nc4)cc(c31)CCC2

Standard InChI:  InChI=1S/C21H22N2O3/c1-21-8-2-4-13-10-16(11-14(18(13)21)5-3-9-21)23-19(24)15-6-7-17(20(25)26)22-12-15/h6-7,10-12H,2-5,8-9H2,1H3,(H,23,24)(H,25,26)

Standard InChI Key:  BCLVLWCSJJEVKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   24.2887   -8.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2887   -9.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9940   -8.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9921  -10.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9858  -10.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6850  -11.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3923  -10.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6993   -8.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6977   -9.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4019  -10.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1082   -9.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1059   -8.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4011   -8.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8123   -8.4558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5213   -8.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2277   -8.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5239   -9.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9381   -8.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6440   -8.4498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6418   -7.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9278   -7.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2248   -7.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3455   -7.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0605   -7.6263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3433   -6.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2805  -10.4914    0.0000 C   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
 15 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
 23 24  1  0
 23 25  2  0
 20 23  1  0
  4 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2398378

   5-[(6a-Methyl-4,5,6,7,8,9-hexahydrophenalen-2-yl)carbamoyl]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: 350.42

Molecular Weight (Monoisotopic): 350.1630

AlogP: 3.96

#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: 0.84

CX Basic pKa: 5.81

CX LogP: 2.84

CX LogD: 1.39

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.88

Np Likeness Score: -0.49

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