3-(2-Carboxy-ethyl)-6-nitro-1H-indole-2-carboxylic acid

Names and Identifiers

Canonical SMILES: O=C(O)CCc1c(C(=O)O)[nH]c2cc([N+](=O)[O-])ccc12

Standard InChI: InChI=1S/C12H10N2O6/c15-10(16)4-3-8-7-2-1-6(14(19)20)5-9(7)13-11(8)12(17)18/h1-2,5,13H,3-4H2,(H,15,16)(H,17,18)

Standard InChI Key: KNNJSTZHQSLHBI-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    5.6917   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -8.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -6.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -8.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -8.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -8.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -8.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -6.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -8.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -9.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250   -6.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -4.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -8.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125   -4.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  9  1  0
  6  3  1  0
  7  1  1  0
  8  4  2  0
  9  8  1  0
 10  3  1  0
 11  6  2  0
 12  5  1  0
 13  5  2  0
 14 18  1  0
 15 11  1  0
 16  7  2  0
 17 14  2  0
 18 10  1  0
 19  7  1  0
 20 14  1  0
  6  4  1  0
 15  9  2  0
M  CHG  2   5   1  12  -1
M  END

Alternative Forms

Parent:

ALA50753
3-(2-carboxyethyl)-6-nitro-1H-indole-2-carboxylic acid

Associated Targets(Human)

FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)

Discover Target: FBP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Grin1 Glutamate NMDA receptor (6467 Activities)

Discover Target: Grin1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 278.22	Molecular Weight (Monoisotopic): 278.0539	AlogP: 1.79	#Rotatable Bonds: 5
Polar Surface Area: 133.53	Molecular Species: ACID	HBA: 4	HBD: 3
#RO5 Violations: ┄	HBA (Lipinski): 8	HBD (Lipinski): 3	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 3.26	CX Basic pKa: ┄	CX LogP: 1.67	CX LogD: -5.04
Aromatic Rings: 2	Heavy Atoms: 20	QED Weighted: 0.56	Np Likeness Score: -0.57

References

1. Salituro FG, Harrison BL, Baron BM, Nyce PL, Stewart KT, Kehne JH, White HS, McDonald IA.. (1992) 3-(2-Carboxyindol-3-yl)propionic acid-based antagonists of the N-methyl-D-aspartic acid receptor associated glycine binding site., 35 (10): [PMID:1534125] [10.1021/jm00088a014]
2. Bie J, Liu S, Li Z, Mu Y, Xu B, Shen Z.. (2015) Discovery of novel indole derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase., 90 [PMID:25461330] [10.1016/j.ejmech.2014.11.049]

Source

Source(1):

Scientific Literature