6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobi[2,3-dihydro-1H-indene]-5,5'-disulfonic acid

ID: ALA60432

PubChem CID: 478339

Max Phase: Preclinical

Molecular Formula: C21H24O8S2

Molecular Weight: 468.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H24O8S2/c1-19(2)9-21(13-5-15(22)17(7-11(13)19)30(24,25)26)10-20(3,4)12-8-18(31(27,28)29)16(23)6-14(12)21/h5-8,22-23H,9-10H2,1-4H3,(H,24,25,26)(H,27,28,29)

Standard InChI Key:  KCRHWRGGABYXEI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  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
    0.6292   -2.0417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -2.0625    0.0000 S   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
    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
    2.7000   -1.3375    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
    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
    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
    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
    5.9875   -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
    0.2167   -2.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -1.3250    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
    7.6417   -2.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -2.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0542   -2.0625    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
    1.4542   -3.4792    0.0000 O   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
    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
  2  7  1  0
  3  6  1  0
  4  1  1  0
  5  1  1  0
  6 18  1  0
  7 19  1  0
  8  5  2  0
  9  4  2  0
 10 12  1  0
 11 13  1  0
 12  1  1  0
 13  1  1  0
 14  9  1  0
 15  8  1  0
 16  5  1  0
 17  4  1  0
 18 17  2  0
 19 16  2  0
 20  2  2  0
 21  2  2  0
 22  3  2  0
 23  3  2  0
 24  2  1  0
 25  3  1  0
 26 18  1  0
 27 19  1  0
 28 10  1  0
 29 11  1  0
 30 11  1  0
 31 10  1  0
 11  8  1  0
 10  9  1  0
  7 15  2  0
  6 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA60432

   3,3,3',3'-Tetramethyl-1,1'-spirobi(indan)-6,6'-dihydroxy-5,5'-disulfonic acid

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: 468.55

Molecular Weight (Monoisotopic): 468.0913

AlogP: 3.24

#Rotatable Bonds: 2

Polar Surface Area: 149.20

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -2.32

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 0.23

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: 0.45

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