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

ID: ALA4763296

PubChem CID: 162659155

Max Phase: Preclinical

Molecular Formula: C23H24INO6

Molecular Weight: 537.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)Oc1cc2c(cc1I)-c1c(cc(OC)c(OC)c1OC)CC[C@@H]2NC(C)=O

Standard InChI:  InChI=1S/C23H24INO6/c1-6-20(27)31-18-11-14-15(10-16(18)24)21-13(7-8-17(14)25-12(2)26)9-19(28-3)22(29-4)23(21)30-5/h6,9-11,17H,1,7-8H2,2-5H3,(H,25,26)/t17-/m0/s1

Standard InChI Key:  NYYGCVWKYIPXKX-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

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    3.1931   -2.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -2.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116   -2.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116   -1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8982   -1.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2478   -1.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0522   -1.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4136   -2.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2307   -2.0218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6472   -2.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4643   -2.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2465   -3.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0674   -2.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2647   -2.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0254   -3.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5878   -4.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3926   -4.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6282   -3.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9530   -4.7502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7483   -4.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3087   -5.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1040   -4.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9832   -3.7795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3512   -5.1276    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -3.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928   -4.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4839   -2.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7765   -2.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853   -1.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776   -1.6347    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
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  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
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  4 15  1  0
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 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 21 24  2  0
 17 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:

   

   ALA4763296

   ---

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: 537.35

Molecular Weight (Monoisotopic): 537.0648

AlogP: 4.20

#Rotatable Bonds: 6

Polar Surface Area: 83.09

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.26

Np Likeness Score: 0.69

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