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

ID: ALA4790387

PubChem CID: 162669085

Max Phase: Preclinical

Molecular Formula: C24H27NO5

Molecular Weight: 409.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1/COc2cc3c(cc21)-c1c(cc(OC)c(OC)c1OC)CC[C@@H]3NC(C)=O

Standard InChI:  InChI=1S/C24H27NO5/c1-6-14-12-30-20-11-17-18(10-16(14)20)22-15(7-8-19(17)25-13(2)26)9-21(27-3)23(28-4)24(22)29-5/h6,9-11,19H,7-8,12H2,1-5H3,(H,25,26)/b14-6-/t19-/m0/s1

Standard InChI Key:  ZWEQMVLEDWGTSY-COXIKBTRSA-N

Molfile:  

 
     RDKit          2D

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   22.1577  -16.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8646  -16.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5762  -16.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5762  -15.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8628  -15.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2124  -15.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0169  -15.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3782  -16.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1953  -16.0668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6118  -16.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4289  -16.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2111  -17.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0320  -16.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2294  -17.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9900  -17.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5572  -18.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3631  -18.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5928  -17.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7978  -18.9040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2607  -19.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4939  -19.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7980  -19.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0790  -19.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8646  -17.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1574  -18.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4485  -16.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7411  -16.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4499  -15.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7423  -15.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  4  2  0
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  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
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  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
 23 24  1  0
  3 25  1  0
 25 26  1  0
  2 27  1  0
 27 28  1  0
  1 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790387

   ---

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: 409.48

Molecular Weight (Monoisotopic): 409.1889

AlogP: 4.30

#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: 3.14

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.82

Np Likeness Score: 1.04

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