6-((1-hydroxynaphthalen-4-ylamino)-dioxysulfone)-2H-naphtho[1,8-bc]thiophen-2-one

ID: ALA1669041

PubChem CID: 53317843

Max Phase: Preclinical

Molecular Formula: C21H13NO5S2

Molecular Weight: 423.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Sc2ccc(OS(=O)(=O)Nc3ccc(O)c4ccccc34)c3cccc1c23

Standard InChI:  InChI=1S/C21H13NO5S2/c23-17-9-8-16(12-4-1-2-5-13(12)17)22-29(25,26)27-18-10-11-19-20-14(18)6-3-7-15(20)21(24)28-19/h1-11,22-23H

Standard InChI Key:  RHZXQMIVPBAHBH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    4.9031  -10.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6183  -10.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3331  -10.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021   -9.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6140   -8.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3297   -9.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0431   -8.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421   -8.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3216   -7.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6112   -8.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7577   -9.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953   -7.6871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8913   -4.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8901   -5.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6046   -5.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184   -5.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0333   -5.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7478   -5.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7431   -4.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0277   -3.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6028   -3.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3171   -4.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7701   -3.1667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -3.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123   -2.4556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6065   -6.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8934   -6.8626    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3056   -6.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932   -7.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 14 15  2  0
 15 16  1  0
 21 13  2  0
  1  2  2  0
 22 16  2  0
  7  8  2  0
 16 17  1  0
  5  4  2  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  4  1  1  0
 19 20  2  0
 20 22  1  0
 21 22  1  0
  9 10  2  0
 10  5  1  0
 23 21  1  0
  7 11  1  0
 23 24  1  0
 20 24  1  0
  2  3  1  0
 24 25  2  0
 10 12  1  0
 15 26  1  0
  5  6  1  0
 26 27  1  0
 27 12  1  0
  3  6  2  0
 27 28  2  0
 13 14  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1669041

   (3-oxo-2-thiatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaen-9-yl) N-(4-hydroxynaphthalen-1-yl)sulfamate

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: 423.47

Molecular Weight (Monoisotopic): 423.0235

AlogP: 4.68

#Rotatable Bonds: 4

Polar Surface Area: 92.70

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.18

CX Basic pKa: ┄

CX LogP: 4.14

CX LogD: 4.08

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -0.36

References

1. Jung HJ, Kim KH, Kim ND, Han G, Kwon HJ..  (2011)  Identification of a novel small molecule targeting UQCRB of mitochondrial complex III and its anti-angiogenic activity.,  21  (3): [PMID:21215626] [10.1016/j.bmcl.2010.12.002]

Source

Source(1):

• Scientific Literature