1',4-dihydroxy-1,6'-dimethyl-6,7-dihydro-2,2'-binaphthyl-5,5',8,8'-tetraone

ID: ALA1097168

PubChem CID: 46888888

Max Phase: Preclinical

Molecular Formula: C22H16O6

Molecular Weight: 376.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)c2c(ccc(-c3cc(O)c4c(c3C)C(=O)CCC4=O)c2O)C1=O

Standard InChI:  InChI=1S/C22H16O6/c1-9-7-16(25)19-12(21(9)27)4-3-11(22(19)28)13-8-17(26)20-15(24)6-5-14(23)18(20)10(13)2/h3-4,7-8,26,28H,5-6H2,1-2H3

Standard InChI Key:  BILDVPLFDVMZBG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -0.2002  -11.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2080  -10.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227  -10.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9152  -11.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5092  -10.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5093  -11.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186  -11.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322  -11.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9321  -10.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2183   -9.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171   -9.1710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2176  -12.4679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941  -12.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470   -9.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4809  -11.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821  -12.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7672  -12.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7690  -11.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0536  -11.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528  -12.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3375  -12.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224  -12.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271  -11.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3431  -11.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7715  -10.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7653  -13.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358  -13.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475  -10.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  9 14  1  0
  3  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  1  0
 17 20  1  0
  5 10  1  0
 19 18  1  0
 18 15  1  0
  6  7  1  0
  7  8  1  0
 19 20  2  0
  8  9  2  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
 10 11  2  0
 23 24  2  0
 24 19  1  0
  5  2  2  0
 18 25  2  0
  7 12  2  0
 17 26  2  0
  1  6  2  0
 21 27  1  0
  1 13  1  0
 24 28  1  0
 23  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097168

   5-Hydroxy-6-(4-hydroxy-1-methyl-5,8-dioxo-6,7-dihydronaphthalen-2-yl)-2-methylnaphthalene-1,4-dione

Molecule Features

Natural Product: Yes

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: 376.36

Molecular Weight (Monoisotopic): 376.0947

AlogP: 3.56

#Rotatable Bonds: 1

Polar Surface Area: 108.74

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.44

CX Basic pKa: ┄

CX LogP: 3.91

CX LogD: 3.60

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.79

Np Likeness Score: 1.37

References

1. Sreelatha T, Hymavathi A, Murthy JM, Rani PU, Rao JM, Babu KS..  (2010)  Bioactivity-guided isolation of mosquitocidal constituents from the rhizomes of Plumbago capensis Thunb.,  20  (9): [PMID:20347303] [10.1016/j.bmcl.2010.02.107]

Source

Source(1):

• Scientific Literature