2-(5-(5-Hydroxypyridin-2-yl)pent-4-ynamido)cyclohex-1-ene-1-carboxylic acid

ID: ALA4099278

PubChem CID: 137659759

Max Phase: Preclinical

Molecular Formula: C17H18N2O4

Molecular Weight: 314.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCC#Cc1ccc(O)cn1)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C17H18N2O4/c20-13-10-9-12(18-11-13)5-1-4-8-16(21)19-15-7-3-2-6-14(15)17(22)23/h9-11,20H,2-4,6-8H2,(H,19,21)(H,22,23)

Standard InChI Key:  TXQSOFHYCDYPCC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   24.1387  -19.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1376  -20.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8456  -21.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5553  -20.7659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5525  -19.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8439  -19.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2564  -19.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9626  -19.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6687  -18.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3780  -19.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0841  -18.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7934  -19.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0811  -17.8858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4995  -18.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2055  -19.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9096  -18.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9107  -17.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2016  -17.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4914  -17.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2048  -19.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4967  -20.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9121  -20.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4296  -21.1744    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
  7  8  3  0
  5  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  2  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  2  0
 20 22  1  0
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099278

   ---

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: 314.34

Molecular Weight (Monoisotopic): 314.1267

AlogP: 1.95

#Rotatable Bonds: 4

Polar Surface Area: 99.52

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.65

CX Basic pKa: 3.80

CX LogP: 0.80

CX LogD: -1.77

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -0.01

References

1. Bobileva O, Ikaunieks M, Duburs G, Mandrika I, Petrovska R, Klovins J, Loza E..  (2017)  Synthesis and evaluation of (E)-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists.,  25  (16): [PMID:28668361] [10.1016/j.bmc.2017.06.028]

Source

Source(1):

• Scientific Literature