N-((7S)-1,2,3-trimethoxy-11-methylene-6,7,10,11-tetrahydro-5H-benzo[6,7]cyclohepta[1,2-f]benzofuran-7-yl)acetamide

ID: ALA4800456

PubChem CID: 154573904

Max Phase: Preclinical

Molecular Formula: C23H25NO5

Molecular Weight: 395.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1COc2cc3c(cc21)-c1c(cc(OC)c(OC)c1OC)CC[C@@H]3NC(C)=O

Standard InChI:  InChI=1S/C23H25NO5/c1-12-11-29-19-10-16-17(9-15(12)19)21-14(6-7-18(16)24-13(2)25)8-20(26-3)22(27-4)23(21)28-5/h8-10,18H,1,6-7,11H2,2-5H3,(H,24,25)/t18-/m0/s1

Standard InChI Key:  DQVCQNGCZCOGHU-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   12.5165  -15.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5165  -16.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2234  -16.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9350  -16.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9350  -15.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2216  -15.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5712  -14.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3756  -15.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7370  -15.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5541  -15.8191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9706  -16.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7877  -16.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5699  -17.2253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3908  -16.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5881  -16.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3488  -17.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9160  -18.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7219  -17.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9516  -17.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1566  -18.6563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6195  -19.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8527  -18.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1568  -19.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2234  -17.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5162  -17.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8073  -16.6592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0999  -16.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8087  -15.0232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1010  -15.4320    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
 20 18  1  0
 21 20  1  0
 22 21  1  0
 17 22  1  0
 22 23  2  0
  3 24  1  0
 24 25  1  0
  2 26  1  0
 26 27  1  0
  1 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4800456

   ---

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: 395.46

Molecular Weight (Monoisotopic): 395.1733

AlogP: 3.91

#Rotatable Bonds: 4

Polar Surface Area: 66.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.85

Np Likeness Score: 0.96

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