methyl 4-(1-(2-(1H-indol-3-yl)ethyl)-3-acetyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)benzoate

ID: ALA478141

PubChem CID: 3157599

Max Phase: Preclinical

Molecular Formula: C24H22N2O5

Molecular Weight: 418.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BAS 8770945 | CHEMBL478141|BAS 8770945|methyl 4-{3-acetyl-4-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-oxo-2,5-dihydro-1H-pyrrol-2-yl}benzoate|BAS 08770945|SCHEMBL15563841|BDBM50006934|AKOS000570026|AKOS022097037|methyl 4-[3-acetyl-4-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-oxo-2H-pyrrol-2-yl]benzoate|AN-465/42126251

Canonical SMILES:  COC(=O)c1ccc(C2C(C(C)=O)=C(O)C(=O)N2CCc2c[nH]c3ccccc23)cc1

Standard InChI:  InChI=1S/C24H22N2O5/c1-14(27)20-21(15-7-9-16(10-8-15)24(30)31-2)26(23(29)22(20)28)12-11-17-13-25-19-6-4-3-5-18(17)19/h3-10,13,21,25,28H,11-12H2,1-2H3

Standard InChI Key:  RYWFTNOOUZJXNY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.3521    0.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9256    0.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8392    1.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0322    1.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6198    1.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1721    0.4384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7993    0.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6964    2.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4521    2.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.2804    2.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6140   -0.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4427   -1.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5850   -3.0571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9971   -2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7779   -2.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6937   -2.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9426   -1.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2751   -2.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3635   -3.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1148   -3.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7855   -0.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7867   -1.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4993   -0.4621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2144   -0.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  1  1  0
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  9 13  1  0
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  7  8  1  0
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  1  2  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA478141

   methyl 4-{3-acetyl-4-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-oxo-2,5-dihydro-1H-pyrrol-2-yl}benzoate

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: 418.45

Molecular Weight (Monoisotopic): 418.1529

AlogP: 3.48

#Rotatable Bonds: 6

Polar Surface Area: 99.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.71

CX Basic pKa: ┄

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -0.66

References

1. Olla S, Manetti F, Crespan E, Maga G, Angelucci A, Schenone S, Bologna M, Botta M..  (2009)  Indolyl-pyrrolone as a new scaffold for Pim1 inhibitors.,  19  (5): [PMID:19179076] [10.1016/j.bmcl.2009.01.005]

2. Zimmerman SS, Khatri A, Garnier-Amblard EC, Mullasseril P, Kurtkaya NL, Gyoneva S, Hansen KB, Traynelis SF, Liotta DC..  (2014)  Design, synthesis, and structure-activity relationship of a novel series of GluN2C-selective potentiators.,  57  (6): [PMID:24512267] [10.1021/jm401695d]

3.  (2014)  NMDA receptor modulators and uses related thereto, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data