(1R,5aS,6R,9aS)-1-(hydroxymethyl)-1,5a-dimethyl-7-methylene-6-((E)-2-(2-oxo-2,5-dihydrofuran-3-yl)ethenyl)octahydro-1H-benzo[c]azepin-3(2H)-one

ID: ALA4476790

PubChem CID: 155538663

Max Phase: Preclinical

Molecular Formula: C20H27NO4

Molecular Weight: 345.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H]2[C@@](C)(CCC(=O)N[C@@]2(C)CO)[C@@H]1/C=C/C1=CCOC1=O

Standard InChI:  InChI=1S/C20H27NO4/c1-13-4-7-16-19(2,10-8-17(23)21-20(16,3)12-22)15(13)6-5-14-9-11-25-18(14)24/h5-6,9,15-16,22H,1,4,7-8,10-12H2,2-3H3,(H,21,23)/b6-5+/t15-,16+,19+,20+/m1/s1

Standard InChI Key:  KMWVVYHGNIPQHR-WHCBKWPTSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    3.7833   -7.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -6.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -7.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619   -6.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2740   -5.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2740   -5.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619   -4.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520   -5.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -5.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020   -4.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3918   -6.3175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -4.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0342   -5.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5802   -6.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0624   -6.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2092   -5.5706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8458   -4.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5618   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2762   -3.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2761   -2.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9398   -2.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846   -1.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8596   -1.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6049   -2.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -2.4397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9896   -4.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  9  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  9  1  0
  9  2  1  0
  8 10  1  0
  2 11  1  0
 10 12  1  0
 11 13  1  0
 12 13  1  0
  2  1  1  0
  2  3  1  1
  1 14  1  0
  9 15  1  1
 13 16  2  0
  8 17  1  6
  7 18  1  6
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  2  0
 21 25  2  0
  6 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476790

   ---

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: 345.44

Molecular Weight (Monoisotopic): 345.1940

AlogP: 2.28

#Rotatable Bonds: 3

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.97

CX Basic pKa: ┄

CX LogP: 1.67

CX LogD: 1.67

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: 2.86

References

1. Wang W, Wu Y, Yang K, Wu C, Tang R, Li H, Chen L..  (2019)  Synthesis of novel andrographolide beckmann rearrangement derivatives and evaluation of their HK2-related anti-inflammatory activities.,  173  [PMID:31009914] [10.1016/j.ejmech.2019.04.022]

Source

Source(1):

• Scientific Literature