SID26666750

ID: ALA1601846

Max Phase: Preclinical

Molecular Formula: C12H6O8

Molecular Weight: 278.17

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-107022

Canonical SMILES:  O=c1oc2c(cc1O)oc(=O)c1cc(O)c(O)c(O)c12

Standard InChI:  InChI=1S/C12H6O8/c13-4-1-3-7(9(16)8(4)15)10-6(19-11(3)17)2-5(14)12(18)20-10/h1-2,13-16H

Standard InChI Key:  VYKVZHXHVUVABA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -0.6071    1.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196   -0.6400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179   -1.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    2.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8679   -1.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929    0.0745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571   -1.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821    0.0745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304   -0.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179    1.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8679    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -0.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0
  1 14  1  0
  2 10  1  0
  2 19  1  0
  3 13  1  0
  4 14  2  0
  5 15  1  0
  6 17  1  0
  7 19  2  0
  8 20  1  0
  9 10  1  0
  9 11  2  0
  9 13  1  0
 10 12  2  0
 11 14  1  0
 11 16  1  0
 12 18  1  0
 13 15  2  0
 15 17  1  0
 16 17  2  0
 18 20  2  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1601846

   ---

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: 278.17

Molecular Weight (Monoisotopic): 278.0063

AlogP: 0.72

#Rotatable Bonds: ┄

Polar Surface Area: 141.34

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.69

CX Basic pKa: ┄

CX LogP: 0.28

CX LogD: -0.57

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.35

Np Likeness Score: 1.49

References

1. PubChem BioAssay data set, 

2. Wang Y, Hess TN, Jones V, Zhou JZ, McNeil MR, Andrew McCammon J..  (2011)  Novel inhibitors of Mycobacterium tuberculosis dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD) identified by virtual screening.,  21  (23): [PMID:22014548] [10.1016/j.bmcl.2011.09.094]

3. Seiler CL, Richards KA, Jakubowski HV, McIntee EJ..  (2013)  Identification of new inhibitors for low molecular weight protein tyrosine phosphatase isoform B.,  23  (21): [PMID:24035092] [10.1016/j.bmcl.2013.08.079]

4. Mukherjee S, Sparks R, Metcalf R, Brooks W, Daniel K, Guida WC..  (2016)  Cupriphilic compounds to aid in proteasome inhibition.,  26  (15): [PMID:27311892] [10.1016/j.bmcl.2016.04.075]

5. Laev SS, Salakhutdinov NF, Lavrik OI..  (2017)  Inhibitors of nuclease and redox activity of apurinic/apyrimidinic endonuclease 1/redox effector factor 1 (APE1/Ref-1).,  25  (9): [PMID:28161249] [10.1016/j.bmc.2017.01.028]

6. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Diversity Set V,  [10.6019/CHEMBL4296182]

7. Whitfield H, Hemmings AM, Mills SJ, Baker K, White G, Rushworth S, Riley AM, Potter BVL, Brearley CA..  (2021)  Allosteric Site on SHIP2 Identified Through Fluorescent Ligand Screening and Crystallography: A Potential New Target for Intervention.,  64  (7.0): [PMID:33724834] [10.1021/acs.jmedchem.0c01944]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• CO-ADD antimicrobial screening data