3-((4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-N-(4-fluorophenethyl)-2-methylacrylamide

ID: ALA4078502

PubChem CID: 137648933

Max Phase: Preclinical

Molecular Formula: C23H30FNO

Molecular Weight: 355.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2[C@H](/C=C(\C)C(=O)NCCc3ccc(F)cc3)CC[C@@H](C)[C@H]2CC1

Standard InChI:  InChI=1S/C23H30FNO/c1-15-4-8-19(22-16(2)5-11-21(15)22)14-17(3)23(26)25-13-12-18-6-9-20(24)10-7-18/h6-7,9-10,14-15,19,21H,4-5,8,11-13H2,1-3H3,(H,25,26)/b17-14+/t15-,19+,21-/m1/s1

Standard InChI Key:  BGEKALKTMWNTQD-RFIQQHCTSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    6.6162  -11.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3281  -11.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3281  -10.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162   -9.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9041  -11.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995  -10.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091   -9.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252  -10.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1166  -11.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660  -12.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162  -12.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3306  -12.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0451  -12.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3306  -13.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162  -13.8998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0451  -13.8998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8916   -9.3583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6192   -8.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9017  -13.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1871  -13.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727  -13.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4774  -12.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638  -12.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483  -12.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0510  -13.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652  -13.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334  -12.2499    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  2  0
  9 10  1  0
  1 11  1  1
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
  6 17  1  1
  4 18  1  6
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4078502

   ---

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: 355.50

Molecular Weight (Monoisotopic): 355.2311

AlogP: 5.20

#Rotatable Bonds: 5

Polar Surface Area: 29.10

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.17

CX LogD: 5.17

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.57

Np Likeness Score: 0.77

References

1. Egbewande FA, Nilsson N, White JM, Coster MJ, Davis RA..  (2017)  The design, synthesis, and anti-inflammatory evaluation of a drug-like library based on the natural product valerenic acid.,  27  (14): [PMID:28558967] [10.1016/j.bmcl.2017.05.021]

Source

Source(1):

• Scientific Literature