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

ID: ALA303764

PubChem CID: 478345

Max Phase: Preclinical

Molecular Formula: C21H21N3O8

Molecular Weight: 443.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC2(CC(C)(C)c3cc([N+](=O)[O-])c(O)c([N+](=O)[O-])c32)c2cc(O)c([N+](=O)[O-])cc21

Standard InChI:  InChI=1S/C21H21N3O8/c1-19(2)8-21(11-7-15(25)13(22(27)28)5-10(11)19)9-20(3,4)12-6-14(23(29)30)18(26)17(16(12)21)24(31)32/h5-7,25-26H,8-9H2,1-4H3

Standard InChI Key:  AEPFEKCKSRFWJD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    2.6917   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.4542   -2.0417    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
    4.7542   -2.0625    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
    3.1042   -3.4792    0.0000 N   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
    0.6292   -2.0417    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
    3.2792   -0.7500    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
    1.8750   -1.3292    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
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    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
    2.6917   -4.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -1.3250    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
    0.2125   -2.7542    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   -3.4792    0.0000 O   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
    2.5667   -0.3375    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
    4.5292   -4.2875    0.0000 C   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
  2  3  1  0
  3  1  1  0
  4  5  1  0
  5  1  2  0
  6  2  1  0
  7  3  2  0
  8  1  1  0
  9 20  1  0
 10  4  1  0
 11  9  1  0
 12  6  2  0
 13  7  1  0
 14 17  1  0
 15  4  2  0
 16  2  1  0
 17  2  1  0
 18 12  1  0
 19  6  1  0
 20 19  2  0
 21  8  1  0
 22 10  1  0
 23 11  1  0
 24  8  2  0
 25 10  2  0
 26 11  2  0
 27  5  1  0
 28 20  1  0
 29 13  1  0
 30 13  1  0
 31 14  1  0
 32 14  1  0
 15  7  1  0
 13 16  1  0
 14 12  1  0
  9 18  2  0
M  CHG  6   8   1  10   1  11   1  21  -1  22  -1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA303764

   1,1,1',1'-Tetramethyl-4',6,6'-trinitro-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: 443.41

Molecular Weight (Monoisotopic): 443.1329

AlogP: 4.47

#Rotatable Bonds: 3

Polar Surface Area: 169.88

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.28

CX Basic pKa: ┄

CX LogP: 5.14

CX LogD: 1.74

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: 0.22

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