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

ID: ALA4559740

PubChem CID: 155558113

Max Phase: Preclinical

Molecular Formula: C27H30N2O7

Molecular Weight: 494.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H]2[C@@](C)(CCC(=O)N[C@@]2(C)COC(=O)c2ccccc2[N+](=O)[O-])[C@@H]1/C=C/C1=CCOC1=O

Standard InChI:  InChI=1S/C27H30N2O7/c1-17-8-11-22-26(2,20(17)10-9-18-13-15-35-24(18)31)14-12-23(30)28-27(22,3)16-36-25(32)19-6-4-5-7-21(19)29(33)34/h4-7,9-10,13,20,22H,1,8,11-12,14-16H2,2-3H3,(H,28,30)/b10-9+/t20-,22+,26+,27+/m1/s1

Standard InChI Key:  PSRZOVZJXWISDO-ATGHPYMTSA-N

Molfile:  

 
     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   24.3465   -6.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7687   -5.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5572   -6.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1178   -5.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8231   -5.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8231   -4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1178   -3.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4146   -4.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4126   -5.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7707   -3.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9682   -5.4737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9683   -3.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6140   -4.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6230   -5.9267    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.7968   -4.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4084   -3.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1177   -3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8253   -2.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8252   -1.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4826   -1.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2299   -0.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4127   -0.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1604   -1.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2605   -1.6324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5320   -3.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1637   -6.2280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5723   -6.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3895   -6.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1637   -7.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7953   -7.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6117   -7.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0211   -6.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6081   -6.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7930   -6.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3853   -8.3509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5681   -8.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7926   -9.0594    0.0000 O   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
  9 14  1  1
 13 15  2  0
  8 16  1  6
  7 17  1  6
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  2  0
 20 24  2  0
  6 25  2  0
  2  3  1  1
  2  1  1  0
  1 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 28  1  0
 30 35  1  0
 35 36  1  0
 35 37  2  0
M  CHG  2  35   1  36  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4559740

   ---

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: 494.54

Molecular Weight (Monoisotopic): 494.2053

AlogP: 4.05

#Rotatable Bonds: 6

Polar Surface Area: 124.84

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.38

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.27

Np Likeness Score: 1.48

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