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

ID: ALA4755840

PubChem CID: 162655808

Max Phase: Preclinical

Molecular Formula: C25H29NO5

Molecular Weight: 423.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(c(OC)c1OC)-c1cc3c(cc1[C@@H](NC(C)=O)CC2)OCC3=C(C)C

Standard InChI:  InChI=1S/C25H29NO5/c1-13(2)19-12-31-21-11-16-18(10-17(19)21)23-15(7-8-20(16)26-14(3)27)9-22(28-4)24(29-5)25(23)30-6/h9-11,20H,7-8,12H2,1-6H3,(H,26,27)/t20-/m0/s1

Standard InChI Key:  XEBOCHQEGBCHRI-FQEVSTJZSA-N

Molfile:  

 
     RDKit          2D

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   32.4923  -16.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1992  -16.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9108  -16.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9108  -15.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1974  -15.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5470  -15.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3514  -15.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7128  -15.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5299  -15.9140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9464  -16.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7635  -16.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5457  -17.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3666  -16.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5639  -16.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3246  -17.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8918  -18.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6977  -18.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9274  -17.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1324  -18.7513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5953  -19.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8285  -19.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1326  -19.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4136  -19.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1326  -20.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1992  -17.5723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4920  -17.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7831  -16.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0757  -16.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7844  -15.1182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0768  -15.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  6  1  1  0
  5  7  1  0
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  8  9  1  0
  9 10  1  6
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 11 13  2  0
  9 14  1  0
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  4 15  1  0
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 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
 23 25  1  0
  3 26  1  0
 26 27  1  0
  2 28  1  0
 28 29  1  0
  1 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755840

   ---

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: 423.51

Molecular Weight (Monoisotopic): 423.2046

AlogP: 4.69

#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: 3.38

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.77

Np Likeness Score: 0.94

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