(E)-2-(5-(3-Hydroxyphenyl)pent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylic acid

ID: ALA4096635

PubChem CID: 137654580

Max Phase: Preclinical

Molecular Formula: C18H17NO4

Molecular Weight: 311.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/C#Cc1cccc(O)c1)NC1=C(C(=O)O)CCCC1

Standard InChI:  InChI=1S/C18H17NO4/c20-14-8-5-7-13(12-14)6-1-4-11-17(21)19-16-10-3-2-9-15(16)18(22)23/h4-5,7-8,11-12,20H,2-3,9-10H2,(H,19,21)(H,22,23)/b11-4+

Standard InChI Key:  QYZMXCUFLXBIQN-NYYWCZLTSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   21.0557   -4.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0546   -4.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7626   -5.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4723   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4694   -4.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7608   -3.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1734   -3.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8795   -3.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5857   -2.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2949   -3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0011   -2.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7103   -3.3346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9980   -2.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4165   -2.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1225   -3.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8266   -2.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8277   -2.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1186   -1.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4084   -2.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1217   -4.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4136   -4.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8290   -4.5605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7624   -6.2183    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  2  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
  3 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096635

   ---

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: 311.34

Molecular Weight (Monoisotopic): 311.1158

AlogP: 2.33

#Rotatable Bonds: 3

Polar Surface Area: 86.63

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.98

CX Basic pKa: ┄

CX LogP: 2.54

CX LogD: -0.94

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: 0.55

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