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

ID: ALA4080571

PubChem CID: 137648763

Max Phase: Preclinical

Molecular Formula: C22H28FNO

Molecular Weight: 341.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2[C@H](/C=C(\C)C(=O)NCc3ccc(F)cc3)CC[C@@H](C)[C@H]2CC1

Standard InChI:  InChI=1S/C22H28FNO/c1-14-4-8-18(21-15(2)5-11-20(14)21)12-16(3)22(25)24-13-17-6-9-19(23)10-7-17/h6-7,9-10,12,14,18,20H,4-5,8,11,13H2,1-3H3,(H,24,25)/b16-12+/t14-,18+,20-/m1/s1

Standard InChI Key:  DAVUQBKACMLZJU-IGXOHMADSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.5786  -11.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2906  -10.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2906   -9.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5786   -9.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666  -10.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8620   -9.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0717   -9.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5877  -10.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0791  -10.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286  -11.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5786  -11.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2931  -12.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0075  -11.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2931  -13.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5786  -13.6165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0075  -13.6165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8541   -9.0749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5817   -8.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8641  -13.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1497  -13.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4355  -13.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216  -13.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212  -14.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406  -14.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1516  -14.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0072  -14.8524    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  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4080571

   ---

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: 341.47

Molecular Weight (Monoisotopic): 341.2155

AlogP: 5.16

#Rotatable Bonds: 4

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: 4.88

CX LogD: 4.88

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: 0.64

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