4,4',7,7'-tetrabromo-3,3,3',3'-tetramethyl-1,1'-spirobi[2,3-dihydro-1H-indene]-5,5',6,6'-tetraol

ID: ALA65504

PubChem CID: 478343

Max Phase: Preclinical

Molecular Formula: C21H20Br4O4

Molecular Weight: 656.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC2(CC(C)(C)c3c(Br)c(O)c(O)c(Br)c32)c2c(Br)c(O)c(O)c(Br)c21

Standard InChI:  InChI=1S/C21H20Br4O4/c1-19(2)5-21(9-7(19)11(22)15(26)17(28)13(9)24)6-20(3,4)8-10(21)14(25)18(29)16(27)12(8)23/h26-29H,5-6H2,1-4H3

Standard InChI Key:  SCVDYKNGBCEKLQ-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
    4.7542   -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
    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
    5.1667   -1.3500    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
    1.8750   -1.3292    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
    5.9875   -1.3417    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
    6.4042   -2.0625    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
    3.2792   -0.7500    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
    3.9292   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -0.6167    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -3.4792    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -3.4917    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.7500   -0.6375    0.0000 Br  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
    7.2292   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -2.0417    0.0000 O   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
    2.5667   -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  2  0
  5  3  2  0
  6  2  1  0
  7  3  1  0
  8  5  1  0
  9  4  1  0
 10  6  2  0
 11 12  1  0
 12  7  2  0
 13 10  1  0
 14 16  1  0
 15 17  1  0
 16  1  1  0
 17  1  1  0
 18  8  1  0
 19  7  1  0
 20  9  1  0
 21  6  1  0
 22 10  1  0
 23 12  1  0
 24 13  1  0
 25 11  1  0
 26 15  1  0
 27 14  1  0
 28 14  1  0
 29 15  1  0
 15  5  1  0
 14  4  1  0
 11  8  2  0
 13  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA65504

   4,4',7,7'-tetrabromo-1,1,1',1'-tetramethyl-3,3'-spirobi[2H-indene]-5,5',6,6'-tetrol

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: 656.00

Molecular Weight (Monoisotopic): 651.8095

AlogP: 7.21

#Rotatable Bonds: ┄

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.32

CX Basic pKa: ┄

CX LogP: 7.79

CX LogD: 7.38

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.23

Np Likeness Score: 0.49

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