Diethyl 4-Phenyl-1-(pyrazine-2-carbonyl)-1,4-dihydropyridine-3,5-dicarboxylate

ID: ALA4522414

PubChem CID: 155543026

Max Phase: Preclinical

Molecular Formula: C22H21N3O5

Molecular Weight: 407.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=CN(C(=O)c2cnccn2)C=C(C(=O)OCC)C1c1ccccc1

Standard InChI:  InChI=1S/C22H21N3O5/c1-3-29-21(27)16-13-25(20(26)18-12-23-10-11-24-18)14-17(22(28)30-4-2)19(16)15-8-6-5-7-9-15/h5-14,19H,3-4H2,1-2H3

Standard InChI Key:  VMSMCKQSUZIPQE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.5730  -21.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889  -22.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0020  -21.9574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7178  -22.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7206  -23.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0075  -23.6074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917  -23.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5703  -21.1372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8544  -20.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516  -19.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1358  -19.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4227  -19.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068  -19.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0062  -19.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1330  -18.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5647  -19.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8433  -17.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564  -17.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2722  -17.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750  -18.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2806  -19.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9936  -19.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909  -18.6574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7039  -18.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7012  -17.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7095  -19.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2833  -20.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 20 21  2  0
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 18 23  1  0
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 26 27  1  0
 27 28  1  0
 25 29  2  0
 24 30  2  0
  9 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522414

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 407.43

Molecular Weight (Monoisotopic): 407.1481

AlogP: 2.61

#Rotatable Bonds: 6

Polar Surface Area: 98.69

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.68

Np Likeness Score: -0.69

References

1. Valente S, Mellini P, Spallotta F, Carafa V, Nebbioso A, Polletta L, Carnevale I, Saladini S, Trisciuoglio D, Gabellini C, Tardugno M, Zwergel C, Cencioni C, Atlante S, Moniot S, Steegborn C, Budriesi R, Tafani M, Del Bufalo D, Altucci L, Gaetano C, Mai A..  (2016)  1,4-Dihydropyridines Active on the SIRT1/AMPK Pathway Ameliorate Skin Repair and Mitochondrial Function and Exhibit Inhibition of Proliferation in Cancer Cells.,  59  (4): [PMID:26689352] [10.1021/acs.jmedchem.5b01117]

2. Suenkel B, Valente S, Zwergel C, Weiss S, Di Bello E, Fioravanti R, Aventaggiato M, Amorim JA, Garg N, Kumar S, Lombard DB, Hu T, Singh PK, Tafani M, Palmeira CM, Sinclair D, Mai A, Steegborn C..  (2022)  Potent and Specific Activators for Mitochondrial Sirtuins Sirt3 and Sirt5.,  65  (20.0): [PMID:36228194] [10.1021/acs.jmedchem.2c01215]

Source

Source(1):

• Scientific Literature