Methyl 2-((1S,5R,8S,8aS)-1-(3-chloro-2-methylpropanamido)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylate

ID: ALA4450376

PubChem CID: 155521120

Max Phase: Preclinical

Molecular Formula: C20H28ClNO4

Molecular Weight: 381.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(C(=O)OC)[C@@H]1CC[C@H](C)[C@H]2C(=C(C)C(=O)[C@H]2NC(=O)C(C)CCl)C1

Standard InChI:  InChI=1S/C20H28ClNO4/c1-10-6-7-14(12(3)20(25)26-5)8-15-13(4)18(23)17(16(10)15)22-19(24)11(2)9-21/h10-11,14,16-17H,3,6-9H2,1-2,4-5H3,(H,22,24)/t10-,11?,14+,16-,17-/m0/s1

Standard InChI Key:  ZZVZUPDFFVRSLU-QBQPCYGGSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    6.2139  -19.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9553  -19.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1337  -20.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7854  -21.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6114  -21.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2766  -20.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4703  -19.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7683  -19.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1407  -20.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4549  -20.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0226  -21.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388  -19.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051  -18.6767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2218  -18.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9616  -22.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900  -22.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7837  -22.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1341  -22.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2554  -21.5294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9561  -23.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793  -19.1296    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611  -18.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979  -17.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803  -18.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5786  -17.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538  -17.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0906  -16.3185    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
  1  2  1  0
  2  3  1  0
  6  4  1  0
  3  5  1  0
  4  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  2  0
 10 11  1  0
  9 12  2  0
  8 13  1  1
  1 14  1  1
  5 15  1  1
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
  7 21  1  6
 13 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4450376

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 381.90

Molecular Weight (Monoisotopic): 381.1707

AlogP: 3.03

#Rotatable Bonds: 5

Polar Surface Area: 72.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.41

CX Basic pKa: ┄

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: 1.27

References

1. Li G, Obul M, Zhao JY, Liu GY, Lu W, Aisa HA..  (2019)  Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents.,  29  (19): [PMID:31439378] [10.1016/j.bmcl.2019.08.009]

Source

Source(1):

• Scientific Literature