1H,1'H-[2,2']Biindolylidene-3,3'-dione

ID: ALA599552

Max Phase: Phase

Molecular Formula: C16H10N2O2

Molecular Weight: 262.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ao201 | Ci 73000 | Indigo | Indigo blue | Indigo whole | Indigofera orthocarpa whole | Indigofera tinctoria | Indigofera tinctoria whole | Indigotin | Nila whole | Nili whole | Nilika whole | Nilini whole | True indigo whole | C.I.73000 | NSC-8645

Canonical SMILES:  O=C1/C(=C2\Nc3ccccc3C2=O)Nc2ccccc21

Standard InChI:  InChI=1S/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17-18H/b14-13+

Standard InChI Key:  COHYTHOBJLSHDF-BUHFOSPRSA-N

Molfile:  

     RDKit          2D

 20 23  0  0  0  0  0  0  0  0999 V2000
    0.4653  -17.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4642  -18.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791  -18.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773  -16.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928  -17.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976  -18.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6853  -18.4725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672  -17.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775  -17.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278  -16.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924  -17.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827  -18.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793  -17.1274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319  -19.2484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2646  -17.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2650  -18.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750  -18.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6852  -18.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809  -17.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9703  -16.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  9 10  2  0
  5  6  1  0
  8 11  2  0
 11 12  1  0
  2  3  1  0
 12 16  1  0
 15 13  1  0
 13 11  1  0
  3  6  2  0
 12 14  2  0
  1  2  2  0
  5  4  2  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
 20 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA599552

   INDIGO

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: 262.27

Molecular Weight (Monoisotopic): 262.0742

AlogP: 2.81

#Rotatable Bonds: ┄

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.18

CX Basic pKa: ┄

CX LogP: 2.65

CX LogD: 2.65

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.72

Np Likeness Score: 0.31

References

1. McGovern SL, Shoichet BK..  (2003)  Kinase inhibitors: not just for kinases anymore.,  46  (8): [PMID:12672248] [10.1021/jm020427b]

2. Sasaki S, Mizushima T, Hashimoto T, Maeda M, Kazuhisa S.  (1994)  3-Acetoxy-2,2-bi-1H-indol as a novel inhibitor of ATP binding to DnaA, the protein initiating chromosomal replication in escherichia coli,  4  (14): [10.1016/S0960-894X(00)80378-9]

3. Guengerich FP, Sorrells JL, Schmitt S, Krauser JA, Aryal P, Meijer L..  (2004)  Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis.,  47  (12): [PMID:15163202] [10.1021/jm030561b]

4. Fujita Y, Yonehara M, Tetsuhashi M, Noguchi-Yachide T, Hashimoto Y, Ishikawa M..  (2010)  beta-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: improvement of solubility by disruption of molecular planarity.,  18  (3): [PMID:20060304] [10.1016/j.bmc.2009.12.036]

5. PubChem BioAssay data set, 

6. Chen M, Gan L, Lin S, Wang X, Li L, Li Y, Zhu C, Wang Y, Jiang B, Jiang J, Yang Y, Shi J..  (2012)  Alkaloids from the root of Isatis indigotica.,  75  (6): [PMID:22694318] [10.1021/np3002833]

7. Klein LL, Petukhova V, Wan B, Wang Y, Santasiero BD, Lankin DC, Pauli GF, Franzblau SG..  (2014)  A novel indigoid anti-tuberculosis agent.,  24  (1): [PMID:24314672] [10.1016/j.bmcl.2013.11.024]

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. Ibrahim HS, Abou-Seri SM, Ismail NS, Elaasser MM, Aly MH, Abdel-Aziz HA..  (2016)  Bis-isatin hydrazones with novel linkers: Synthesis and biological evaluation as cytotoxic agents.,  108  [PMID:26706352] [10.1016/j.ejmech.2015.11.047]

12. Unpublished dataset, 

13. Lin L, Dai Y, Xia Y..  (2022)  An overview of aryl hydrocarbon receptor ligands in the Last two decades (2002-2022): A medicinal chemistry perspective.,  244  [PMID:36274276] [10.1016/j.ejmech.2022.114845]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates