3,3,3',3'-tetramethyl-1,1'-spirobi(indan)-6,6'-dihydroxy-5,5'-bisurea

ID: ALA305357

PubChem CID: 478337

Max Phase: Preclinical

Molecular Formula: C23H28N4O4

Molecular Weight: 424.50

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H28N4O4/c1-21(2)9-23(13-7-17(28)15(5-11(13)21)26-19(24)30)10-22(3,4)12-6-16(27-20(25)31)18(29)8-14(12)23/h5-8,28-29H,9-10H2,1-4H3,(H3,24,26,30)(H3,25,27,31)

Standard InChI Key:  BBELNFJEOKRGCV-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
    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
    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
    1.8750   -1.3292    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
    0.2250   -1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -2.0417    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
    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
    0.6375   -0.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4667   -2.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -3.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -1.3250    0.0000 N   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  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 20  1  0
 13 21  1  0
 14  5  1  0
 15  4  1  0
 16 18  1  0
 17 19  1  0
 18 13  1  0
 19 12  1  0
 20 11  2  0
 21 10  2  0
 22 16  2  0
 23 17  2  0
 24 17  1  0
 25 16  1  0
 26 20  1  0
 27 21  1  0
 28  6  1  0
 29  7  1  0
 30  7  1  0
 31  6  1  0
  7  5  1  0
  6  4  1  0
 13 14  2  0
 12 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA305357

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

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: 424.50

Molecular Weight (Monoisotopic): 424.2111

AlogP: 3.73

#Rotatable Bonds: 2

Polar Surface Area: 150.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.62

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.10

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: 0.17

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