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

ID: ALA4085993

PubChem CID: 137642651

Max Phase: Preclinical

Molecular Formula: C20H33NO

Molecular Weight: 303.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H33NO/c1-13(2)10-11-21-20(22)16(5)12-17-8-6-14(3)18-9-7-15(4)19(17)18/h12-14,17-18H,6-11H2,1-5H3,(H,21,22)/b16-12+/t14-,17+,18-/m1/s1

Standard InChI Key:  DIZAKGFPLKJSPV-JZGALHJVSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    5.9203  -11.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6323  -11.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6323  -10.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9203   -9.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2082  -11.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2037  -10.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133  -10.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294  -10.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4208  -11.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702  -12.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9203  -12.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6347  -12.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3492  -12.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6347  -13.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9203  -14.0582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3492  -14.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958   -9.5166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9234   -9.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2058  -13.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4914  -14.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7772  -13.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796  -12.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615  -14.0533    0.0000 C   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  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085993

   ---

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: 303.49

Molecular Weight (Monoisotopic): 303.2562

AlogP: 4.87

#Rotatable Bonds: 5

Polar Surface Area: 29.10

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 4.62

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: 1.41

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