3,3,3',3'-tetramethyl-1,1'-spirobi(indan)-5,5',6,6'-tetrol tetrasulfate

ID: ALA292736

PubChem CID: 10509626

Max Phase: Preclinical

Molecular Formula: C21H20K4O16S4

Molecular Weight: 660.68

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H24O16S4.4K/c1-19(2)9-21(13-7-17(36-40(28,29)30)15(5-11(13)19)34-38(22,23)24)10-20(3,4)12-6-16(35-39(25,26)27)18(8-14(12)21)37-41(31,32)33;;;;/h5-8H,9-10H2,1-4H3,(H,22,23,24)(H,25,26,27)(H,28,29,30)(H,31,32,33);;;;/q;4*+1/p-4

Standard InChI Key:  AQINOYIEBRTDSI-UHFFFAOYSA-J

Molfile:  

     RDKit          2D

 45 44  0  0  0  0  0  0  0  0999 V2000
   -0.8833   -2.4375    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
    0.7125   -2.3917    0.0000 S   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
    8.9542   -2.4167    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
    6.8917   -1.7042    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
    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
    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
    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
    6.8917   -3.1375    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
    8.1292   -2.4167    0.0000 O   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
    1.5375   -2.4000    0.0000 O   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
    9.7792   -2.4167    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
   -0.1125   -2.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9542   -3.2417    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
    8.5042   -0.4792    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
    8.9542   -1.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -3.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -1.5667    0.0000 O   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
   10.5792   -2.4667    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
    8.3625    1.2208    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5 26  1  0
  6 25  1  0
  7 23  1  0
  8 24  1  0
  9  3  2  0
 10  4  2  0
 11 20  2  0
 12 19  2  0
 13 12  1  0
 14 11  1  0
 15 17  1  0
 16 18  1  0
 17  2  1  0
 18  2  1  0
 19  4  1  0
 20  3  1  0
 21  9  1  0
 22 10  1  0
 23 14  1  0
 24 11  1  0
 25 12  1  0
 26 13  1  0
 27  8  1  0
 28  7  1  0
 29  6  1  0
 30  5  1  0
 31  7  2  0
 32  8  2  0
 33  8  2  0
 34  6  2  0
 35  6  2  0
 36  7  2  0
 37  5  2  0
 38  5  2  0
 39 15  1  0
 40 15  1  0
 41 16  1  0
 42 16  1  0
 16 10  1  0
 15  9  1  0
 13 22  2  0
 14 21  2  0
M  CHG  8   1   1  27  -1  28  -1  29  -1  30  -1  43   1  44   1  45   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: 660.68

Molecular Weight (Monoisotopic): 659.9947

AlogP: 2.06

#Rotatable Bonds: 8

Polar Surface Area: 254.40

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -2.88

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: -6.70

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.30

Np Likeness Score: 0.47

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