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

ID: ALA302862

PubChem CID: 478341

Max Phase: Preclinical

Molecular Formula: C21H22Br2O2

Molecular Weight: 466.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC2(CC(C)(C)c3cc(Br)c(O)cc32)c2cc(O)c(Br)cc21

Standard InChI:  InChI=1S/C21H22Br2O2/c1-19(2)9-21(13-7-17(24)15(22)5-11(13)19)10-20(3,4)12-6-16(23)18(25)8-14(12)21/h5-8,24-25H,9-10H2,1-4H3

Standard InChI Key:  CIJFECHCVAAGIQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  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
    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
    2.6917   -2.7667    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
    5.9917   -2.7792    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
    6.4042   -2.0625    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
    5.9875   -1.3417    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
    7.2292   -2.0625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -2.0417    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
    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  8  1  0
  7  9  1  0
  8  1  1  0
  9  1  1  0
 10  3  1  0
 11  2  1  0
 12  4  1  0
 13  5  1  0
 14 16  1  0
 15 17  1  0
 16 11  2  0
 17 10  2  0
 18 14  1  0
 19 15  1  0
 20 16  1  0
 21 17  1  0
 22  7  1  0
 23  6  1  0
 24  6  1  0
 25  7  1  0
  7  5  1  0
  6  4  1  0
 15 13  2  0
 14 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA302862

   3,3,3',3'-Tetramethyl-1,1'-spirobi(indan)-5,5'-dibromo-6,6'-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: 466.21

Molecular Weight (Monoisotopic): 463.9987

AlogP: 6.27

#Rotatable Bonds: ┄

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.06

CX Basic pKa: ┄

CX LogP: 6.86

CX LogD: 6.77

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.48

Np Likeness Score: 0.73

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