3,3,3',3'-tetramethyl-5,7'-dinitro-1,1'-spirobi[2,3-dihydro-1H-indene]-6,6'-diol

ID: ALA64554

PubChem CID: 478344

Max Phase: Preclinical

Molecular Formula: C21H22N2O6

Molecular Weight: 398.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC2(CC(C)(C)c3ccc(O)c([N+](=O)[O-])c32)c2cc(O)c([N+](=O)[O-])cc21

Standard InChI:  InChI=1S/C21H22N2O6/c1-19(2)9-21(17-11(19)5-6-15(24)18(17)23(28)29)10-20(3,4)12-7-14(22(26)27)16(25)8-13(12)21/h5-8,24-25H,9-10H2,1-4H3

Standard InChI Key:  MCRHMHKHIGHINP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.9292   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -3.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -2.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -4.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -2.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -3.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -1.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -0.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -3.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5 16  1  0
  6  4  1  0
  7  5  1  0
  8  3  2  0
  9  2  2  0
 10 11  1  0
 11  1  1  0
 12 13  1  0
 13  1  1  0
 14  8  1  0
 15  3  1  0
 16 15  2  0
 17  9  1  0
 18  4  2  0
 19  6  1  0
 20  7  1  0
 21  6  2  0
 22  7  2  0
 23 17  2  0
 24 16  1  0
 25 18  1  0
 26 10  1  0
 27 10  1  0
 28 12  1  0
 29 12  1  0
 12  9  1  0
 10  8  1  0
  5 14  2  0
 23 18  1  0
M  CHG  4   6   1   7   1  19  -1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA64554

   1,1,1',1'-Tetramethyl-4,6'-dinitro-3,3'-spirobi[indane]-5,5'-diol

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: 398.42

Molecular Weight (Monoisotopic): 398.1478

AlogP: 4.56

#Rotatable Bonds: 2

Polar Surface Area: 126.74

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.09

CX Basic pKa: ┄

CX LogP: 5.20

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: 0.36

References

1. Molteni V, Rhodes D, Rubins K, Hansen M, Bushman FD, Siegel JS..  (2000)  A new class of HIV-1 integrase inhibitors: the 3,3,3', 3'-tetramethyl-1,1'-spirobi(indan)-5,5',6,6'-tetrol family.,  43  (10): [PMID:10821715] [10.1021/jm990600c]

Source

Source(1):

• Scientific Literature