3,3,3',3'-tetramethyl-1,1'-spirobi(indan)-5,5'-dibromo-6,6'-diol disulphate

ID: ALA62715

PubChem CID: 10747313

Max Phase: Preclinical

Molecular Formula: C21H20Br2K2O8S2

Molecular Weight: 626.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC2(CC(C)(C)c3cc(Br)c(OS(=O)(=O)[O-])cc32)c2cc(OS(=O)(=O)[O-])c(Br)cc21.[K+].[K+]

Standard InChI:  InChI=1S/C21H22Br2O8S2.2K/c1-19(2)9-21(13-7-17(30-32(24,25)26)15(22)5-11(13)19)10-20(3,4)12-6-16(23)18(8-14(12)21)31-33(27,28)29;;/h5-8H,9-10H2,1-4H3,(H,24,25,26)(H,27,28,29);;/q;2*+1/p-2

Standard InChI Key:  JFECXOOZTZYGHX-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    8.3625    1.2208    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
    4.8375   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -4.5500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7042   -0.2667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000   -0.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -3.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3042   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167    0.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -5.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   -0.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9917    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -4.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -2.4167    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -2.4000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -5.9042    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5 20  1  0
  6 19  1  0
  7  3  2  0
  8  4  2  0
  9 11  1  0
 10 12  1  0
 11  2  1  0
 12  2  1  0
 13 15  2  0
 14 16  2  0
 15  4  1  0
 16  3  1  0
 17  8  1  0
 18  7  1  0
 19 14  1  0
 20 13  1  0
 21 13  1  0
 22 14  1  0
 23  6  1  0
 24  5  1  0
 25  6  2  0
 26  6  2  0
 27  5  2  0
 28  5  2  0
 29 22  1  0
 30 21  1  0
 31  9  1  0
 32  9  1  0
 33 10  1  0
 34 10  1  0
 10  8  1  0
  9  7  1  0
 21 17  2  0
 22 18  2  0
M  CHG  4   1   1  23  -1  24  -1  35   1
M  END

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: 626.34

Molecular Weight (Monoisotopic): 623.9123

AlogP: 5.22

#Rotatable Bonds: 4

Polar Surface Area: 127.20

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -2.39

CX Basic pKa: ┄

CX LogP: 5.91

CX LogD: 1.15

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: 0.62

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