tert-Butyl 7-(4-chlorophenyl)-2,3-dimethyl-5-oxo-2,3,7,8-tetrahydro-3,8a-epidioxypyrano[3,2-c]pyridine-6(5H)-carboxylate

ID: ALA2435143

PubChem CID: 73346352

Max Phase: Preclinical

Molecular Formula: C21H24ClNO6

Molecular Weight: 421.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1O[C@]23CC(c4ccc(Cl)cc4)N(C(=O)OC(C)(C)C)C(=O)C2=C[C@@]1(C)OO3

Standard InChI:  InChI=1S/C21H24ClNO6/c1-12-20(5)10-15-17(24)23(18(25)27-19(2,3)4)16(11-21(15,26-12)29-28-20)13-6-8-14(22)9-7-13/h6-10,12,16H,11H2,1-5H3/t12?,16?,20-,21+/m1/s1

Standard InChI Key:  WZLRPYVOOGOUJR-ZHNZERDHSA-N

Molfile:  

     RDKit          2D

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    8.4922  -28.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4922  -27.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7520  -27.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5247  -27.8682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1095  -28.1300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353  -28.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1235  -27.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117  -28.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0128  -27.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2757  -27.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327  -27.6093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315  -28.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2734  -28.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2779  -26.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185  -28.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057  -28.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3918  -28.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894  -29.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1070  -30.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8179  -29.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756  -30.1063    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8203  -27.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8225  -26.3716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1058  -27.6054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1102  -25.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124  -25.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3957  -26.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909  -25.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9  1  1  6
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  3  4  1  0
  9  5  1  0
  5  6  1  0
  3  6  1  0
  2  7  1  0
  3  8  1  1
  9 10  1  0
  9 14  1  0
 10 11  1  0
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 11 15  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 16  1  0
 19 22  1  0
 12 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2435143

   tert-butyl (1S,8R)-3-(4-chlorophenyl)-8,12-dimethyl-5-oxo-9,10,11-trioxa-4-azatricyclo[6.2.2.01,6]dodec-6-ene-4-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.88

Molecular Weight (Monoisotopic): 421.1292

AlogP: 4.31

#Rotatable Bonds: 1

Polar Surface Area: 74.30

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.76

CX LogD: 4.76

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: 0.45

References

1. Hossain MI, Świtalska M, Peng W, Takashima M, Wang N, Kaiser M, Wietrzyk J, Dan S, Yamori T, Inokuchi T..  (2013)  Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures.,  69  [PMID:24056020] [10.1016/j.ejmech.2013.08.008]

Source

Source(1):

• Scientific Literature