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

ID: ALA4099378

PubChem CID: 137660013

Max Phase: Preclinical

Molecular Formula: C23H30BrNO

Molecular Weight: 416.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H30BrNO/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:  CQIMLMYPHBOQSL-RFIQQHCTSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    7.7369  -11.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4490  -11.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4490  -10.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7369   -9.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0249  -11.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0204  -10.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300  -10.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7460  -10.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2374  -11.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868  -12.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7369  -12.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4514  -12.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1659  -12.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4514  -13.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7369  -13.9873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1659  -13.9873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0124   -9.4457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7401   -9.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0225  -13.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3080  -13.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5936  -13.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5982  -12.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8847  -12.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1692  -12.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1718  -13.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8861  -13.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542  -12.3373    0.0000 Br  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:

   

   ALA4099378

   ---

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: 416.40

Molecular Weight (Monoisotopic): 415.1511

AlogP: 5.83

#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: 5.80

CX LogD: 5.80

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.48

Np Likeness Score: 0.96

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