N-((1S,2R,4aS,5R,8aS)-2-hydroxy-1,4a-dimethyl-6-methylene-5-((E)-2-(2-oxo-2,5-dihydrofuran-3-yl)ethenyl)decahydronaphthalen-1-yl)formamide

ID: ALA4435724

PubChem CID: 155511240

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)(CC[C@@H](O)[C@@]2(C)NC=O)[C@@H]1/C=C/C1=CCOC1=O

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

Standard InChI Key:  VWEPTAOEXREBNO-CRBRZBHVSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   28.0627  -16.3878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6463  -15.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2456  -16.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6621  -17.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8449  -17.1092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0552  -15.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7605  -15.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7605  -14.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0552  -14.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5604  -16.0673    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.3458  -13.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0551  -13.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7627  -12.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7625  -12.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4200  -11.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1673  -10.7455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3500  -10.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0978  -11.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1979  -11.7730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4694  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3499  -15.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3543  -14.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6550  -14.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9469  -14.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9425  -15.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2322  -15.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  1  4  1  0
  4  5  2  0
 22  9  1  0
 21  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 21 10  1  1
 22 11  1  6
  9 12  1  6
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  2  0
 15 19  2  0
  8 20  2  0
 21 22  1  0
 21  2  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25  2  1  0
 25 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4435724

   ---

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: 2.27

#Rotatable Bonds: 4

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: 13.51

CX Basic pKa: ┄

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.47

Np Likeness Score: 3.33

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