3,3,3',3'-tetramethyl-1,1'-spirobi(indan)-6,6'-dihydroxy-5,7'-bisurea

ID: ALA62411

PubChem CID: 478347

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)c3ccc(O)c(NC(N)=O)c32)c2cc(O)c(NC(N)=O)cc21

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

Standard InChI Key:  NBQYMXISJVPDAX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    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
    6.0667   -1.7042    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
    6.0667   -3.1375    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   -1.5917    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
    4.8292   -3.2417    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
    2.3625   -2.4042    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
    5.6542   -0.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -2.4000    0.0000 N   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   -3.1375    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
    5.6500    0.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -0.9667    0.0000 O   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
    6.8875   -0.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -1.6792    0.0000 N   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
    7.3000   -0.9875    0.0000 O   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
    3.4667   -0.6917    0.0000 C   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
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  2  0
  6  2  2  0
  7  8  1  0
  8  1  1  0
  9 10  1  0
 10  1  1  0
 11  3  1  0
 12 18  1  0
 13  5  1  0
 14  4  1  0
 15 14  1  0
 16 17  1  0
 17 12  1  0
 18 11  2  0
 19  6  1  0
 20  4  2  0
 21 15  2  0
 22 16  2  0
 23 19  2  0
 24 15  1  0
 25 16  1  0
 26 18  1  0
 27 20  1  0
 28  7  1  0
 29  7  1  0
 30  9  1  0
 31  9  1  0
  9  6  1  0
  7  5  1  0
 12 13  2  0
 23 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA62411

   3,3,3',3'-Tetramethyl-1,1'-spirobi(indan)-6,6'-dihydroxy-5,7'-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: 8.63

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.10

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: 0.37

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