3,3,3',3'-tetramethyl-1,1'-spirobi(indan)-5,7'-diamino-6,6'-diol Dihydrochloric salt

ID: ALA305598

PubChem CID: 49796254

Max Phase: Preclinical

Molecular Formula: C21H28Cl2N2O2

Molecular Weight: 338.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC2(CC(C)(C)c3ccc(O)c(N)c32)c2cc(O)c(N)cc21.Cl.Cl

Standard InChI:  InChI=1S/C21H26N2O2.2ClH/c1-19(2)9-21(17-11(19)5-6-15(24)18(17)23)10-20(3,4)12-7-14(22)16(25)8-13(12)21;;/h5-8,24-25H,9-10,22-23H2,1-4H3;2*1H

Standard InChI Key:  WBFMTDDLWSNFSB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.5875   -5.3750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    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
    3.9292   -2.8875    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   -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
    6.4042   -2.0625    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
    1.8750   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -3.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -2.0625    0.0000 N   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
    1.4542   -2.0417    0.0000 C   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
    4.5292   -4.2875    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
    2.5667   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9875   -2.0292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5  3  2  0
  6  4  2  0
  7  8  1  0
  8  2  1  0
  9 10  1  0
 10  2  1  0
 11  4  1  0
 12  3  1  0
 13  5  1  0
 14 15  1  0
 15 12  2  0
 16  6  1  0
 17 11  1  0
 18 14  1  0
 19 11  2  0
 20 19  1  0
 21 15  1  0
 22 19  1  0
 23  7  1  0
 24  7  1  0
 25  9  1  0
 26  9  1  0
  9  6  1  0
  7  5  1  0
 20 16  2  0
 14 13  2  0
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: 338.45

Molecular Weight (Monoisotopic): 338.1994

AlogP: 3.91

#Rotatable Bonds: ┄

Polar Surface Area: 92.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.22

CX Basic pKa: 4.59

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: 0.97

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