mebudipine

ID: ALA1095098

Cas Number: 103521-70-6

PubChem CID: 10407950

Max Phase: Preclinical

Molecular Formula: C20H24N2O6

Molecular Weight: 388.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Mebudipine | mebudipine|103521-70-6|CHEMBL1095098|5-O-tert-butyl 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Canonical SMILES:  COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)C)C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C20H24N2O6/c1-11-15(18(23)27-6)17(13-8-7-9-14(10-13)22(25)26)16(12(2)21-11)19(24)28-20(3,4)5/h7-10,17,21H,1-6H3

Standard InChI Key:  YXPRKGBMFPQBDH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    6.9194    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9182    1.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6331    0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3495    1.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3466    2.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6313    2.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6334   -0.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9170   -0.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9148   -1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6274   -1.7092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3438   -1.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3476   -0.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1987   -1.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0567   -1.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0626   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7766   -0.4723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0637    0.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4916   -0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036   -0.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2058    0.7681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881   -0.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7747   -0.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0591   -0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7769    0.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2064    2.4082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4913    1.9967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2048    3.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 11 14  1  0
  1  2  2  0
 12 15  1  0
  3  4  2  0
 15 16  1  0
 15 17  2  0
  4  5  1  0
 16 18  1  0
  2  3  1  0
  8 19  1  0
  5  6  2  0
 19 20  2  0
  7 12  1  0
 19 21  1  0
  8  9  2  0
 21 22  1  0
  9 10  1  0
 22 23  1  0
 10 11  1  0
 22 24  1  0
 11 12  2  0
 22 25  1  0
  3  7  1  0
  6  1  1  0
  9 13  1  0
 26 27  2  0
 26 28  1  0
  1 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1095098

   MEBUDIPINE

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: 388.42

Molecular Weight (Monoisotopic): 388.1634

AlogP: 3.34

#Rotatable Bonds: 4

Polar Surface Area: 107.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -0.84

References

1. Arhancet GB, Woodard SS, Dietz JD, Garland DJ, Wagner GM, Iyanar K, Collins JT, Blinn JR, Numann RE, Hu X, Huang HC..  (2010)  Stereochemical requirements for the mineralocorticoid receptor antagonist activity of dihydropyridines.,  53  (10): [PMID:20408553] [10.1021/jm1002827]

2. Chang CC, Cao S, Kang S, Kai L, Tian X, Pandey P, Dunne SF, Luan CH, Surmeier DJ, Silverman RB..  (2010)  Antagonism of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates toward voltage-dependent L-type Ca2+ channels Ca V 1.3 and Ca V 1.2.,  18  (9): [PMID:20382537] [10.1016/j.bmc.2010.03.038]

3. Arhancet GB, Woodard SS, Iyanar K, Case BL, Woerndle R, Dietz JD, Garland DJ, Collins JT, Payne MA, Blinn JR, Pomposiello SI, Hu X, Heron MI, Huang HC, Lee LF..  (2010)  Discovery of novel cyanodihydropyridines as potent mineralocorticoid receptor antagonists.,  53  (16): [PMID:20672820] [10.1021/jm100506y]

Source

Source(1):

• Scientific Literature