5-[(5,6,6a,7,8,9-Hexahydro-4H-2-phenalenyl)carbamoyl]thiophene-2-carboxylic acid

ID: ALA2398379

PubChem CID: 67391047

Max Phase: Preclinical

Molecular Formula: C19H19NO3S

Molecular Weight: 341.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(C(=O)Nc2cc3c4c(c2)CCCC4CCC3)s1

Standard InChI:  InChI=1S/C19H19NO3S/c21-18(15-7-8-16(24-15)19(22)23)20-14-9-12-5-1-3-11-4-2-6-13(10-14)17(11)12/h7-11H,1-6H2,(H,20,21)(H,22,23)

Standard InChI Key:  HMPOICZXKISJQH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -4.8536  -14.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8536  -15.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556  -14.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1537  -15.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1639  -16.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4599  -17.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7556  -16.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4494  -14.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478  -15.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405  -15.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0412  -14.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7479  -14.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3361  -14.1513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253  -14.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853  -14.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6197  -15.3749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8355  -14.4746    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803  -13.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1707  -13.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1953  -13.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301  -14.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6735  -13.2863    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
 15 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 16  2  0
 22 23  1  0
 22 24  2  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2398379

   5-[(5,6,6a,7,8,9-Hexahydro-4H-2-phenalenyl)carbamoyl]thiophene-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: 341.43

Molecular Weight (Monoisotopic): 341.1086

AlogP: 4.45

#Rotatable Bonds: 3

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.29

CX Basic pKa: ┄

CX LogP: 5.00

CX LogD: 1.57

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.87

Np Likeness Score: -0.80

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