Methyl (E)-3-((5S)-5-acetamido-3-hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo-[a,c]cycloheptene-2-yl)acrylate

ID: ALA4750077

PubChem CID: 162651450

Max Phase: Preclinical

Molecular Formula: C24H27NO7

Molecular Weight: 441.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)/C=C/c1cc2c(cc1O)[C@@H](NC(C)=O)CCc1cc(OC)c(OC)c(OC)c1-2

Standard InChI:  InChI=1S/C24H27NO7/c1-13(26)25-18-8-6-15-11-20(29-2)23(31-4)24(32-5)22(15)17-10-14(7-9-21(28)30-3)19(27)12-16(17)18/h7,9-12,18,27H,6,8H2,1-5H3,(H,25,26)/b9-7+/t18-/m0/s1

Standard InChI Key:  RMVZSQZXNJRJFW-KOEDOTQGSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   13.4492   -7.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4492   -8.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1561   -8.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8677   -8.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8677   -7.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1543   -6.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5039   -6.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3084   -6.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6697   -7.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4869   -7.6224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9033   -8.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7205   -8.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5027   -9.0287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3236   -8.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5209   -8.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2816   -9.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8488   -9.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6488   -9.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8844   -8.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2106  -10.3495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6148  -10.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1759  -11.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9419  -12.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5030  -12.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2690  -13.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1468  -12.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1561   -9.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4489   -9.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7400   -8.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0327   -8.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7414   -6.8266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0338   -7.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  2  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 18 17  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
  3 27  1  0
 27 28  1  0
  2 29  1  0
 29 30  1  0
  1 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4750077

   ---

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: 441.48

Molecular Weight (Monoisotopic): 441.1788

AlogP: 3.39

#Rotatable Bonds: 6

Polar Surface Area: 103.32

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.86

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: 1.01

References

1. Shchegravina ES,Svirshchevskaya EV,Combes S,Allegro D,Barbier P,Gigant B,Varela PF,Gavryushin AE,Kobanova DA,Shchekotikhin AE,Fedorov AY.  (2020)  Discovery of dihydrofuranoallocolchicinoids - Highly potent antimitotic agents with low acute toxicity.,  207  [PMID:32827941] [10.1016/j.ejmech.2020.112724]

Source

Source(1):

• Scientific Literature