(S)-((1S,2R,4aS,5R,8aS)-1-formamido-1,4a-dimethyl-6-methylene-5-((E)-2-(2-oxo-2,5-dihydrofuran-3-yl)ethenyl)decahydronaphthalen-2-yl) 2-amino-3-phenylpropanoate

ID: ALA4573718

PubChem CID: 155563330

Max Phase: Preclinical

Molecular Formula: C29H36N2O5

Molecular Weight: 492.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H]2[C@@](C)(CC[C@@H](OC(=O)[C@@H](N)Cc3ccccc3)[C@@]2(C)NC=O)[C@@H]1/C=C/C1=CCOC1=O

Standard InChI:  InChI=1S/C29H36N2O5/c1-19-9-12-24-28(2,22(19)11-10-21-14-16-35-26(21)33)15-13-25(29(24,3)31-18-32)36-27(34)23(30)17-20-7-5-4-6-8-20/h4-8,10-11,14,18,22-25H,1,9,12-13,15-17,30H2,2-3H3,(H,31,32)/b11-10+/t22-,23+,24+,25-,28+,29+/m1/s1

Standard InChI Key:  ASAMPPUTIZOMGM-PYESZRQUSA-N

Molfile:  

 
     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   26.0593  -26.0057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6549  -25.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2459  -26.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0659  -25.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7712  -24.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7712  -24.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0659  -23.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5711  -25.6837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.3565  -23.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0657  -22.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7734  -22.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7732  -21.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4307  -21.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1780  -20.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3607  -20.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1085  -21.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2086  -21.3894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4801  -23.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3606  -24.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3650  -24.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6656  -23.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9575  -24.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9532  -24.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6485  -26.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8313  -26.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2429  -25.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5378  -24.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8275  -25.2831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5430  -24.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8379  -23.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8430  -22.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5516  -22.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5571  -21.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8515  -21.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1388  -21.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1368  -22.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2532  -23.6577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 20  7  1  0
 19  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
 19  8  1  1
 20  9  1  6
  7 10  1  6
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 13 17  2  0
  6 18  2  0
 19 20  1  0
 19  2  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23  2  1  0
  2  1  1  0
  2  3  1  1
  1 24  1  0
 24 25  2  0
 23 26  1  6
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
 29 37  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4573718

   ---

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: 492.62

Molecular Weight (Monoisotopic): 492.2624

AlogP: 3.39

#Rotatable Bonds: 8

Polar Surface Area: 107.72

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.58

CX Basic pKa: 6.97

CX LogP: 3.60

CX LogD: 3.47

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: 2.42

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