Methyl 17R-8-bromo-2,17-cyclo-aureanindol-15-ene-21-oate

ID: ALA3115631

PubChem CID: 76317845

Max Phase: Preclinical

Molecular Formula: C24H28BrNO2

Molecular Weight: 442.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@]1(C)CC[C@@H]2C3=C1CC[C@@H](C)[C@]3(C)Cc1c2[nH]c2c(Br)cccc12

Standard InChI:  InChI=1S/C24H28BrNO2/c1-13-8-9-17-19-15(10-11-23(17,2)22(27)28-4)20-16(12-24(13,19)3)14-6-5-7-18(25)21(14)26-20/h5-7,13,15,26H,8-12H2,1-4H3/t13-,15-,23+,24+/m1/s1

Standard InChI Key:  HKFNSLXINGGBMX-LEJWENHNSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    2.9731   -6.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9731   -7.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6856   -8.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6856   -6.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2649   -8.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906   -8.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6781   -9.5305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9131   -8.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0878  -10.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3982   -6.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3992   -7.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108   -8.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8259   -7.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8249   -6.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087   -6.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5398   -6.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8211   -6.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3771   -5.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540   -5.0848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6504   -5.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153   -4.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -4.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405   -3.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4333   -3.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128   -2.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1080   -3.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156   -5.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6778   -7.2847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -3.4649    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3 11  1  0
 10  4  1  0
  3  5  1  0
  3  6  1  1
  6  7  1  0
  6  8  2  0
  7  9  1  0
 10 11  2  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  6
 15 27  1  0
 15 17  1  6
 27 18  1  0
 18 22  1  0
 21 19  1  0
 19 20  1  0
 20 18  2  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  4 20  1  0
  4 28  1  6
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3115631

   methyl (1R,12S,13R,17S)-5-bromo-12,13,17-trimethyl-3-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-2(10),4(9),5,7,16(20)-pentaene-17-carboxylate

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: 442.40

Molecular Weight (Monoisotopic): 441.1303

AlogP: 6.28

#Rotatable Bonds: 1

Polar Surface Area: 42.09

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.75

CX LogD: 5.75

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: 1.61

References

1. Marcos IS, Moro RF, Costales I, Basabe P, Díez D, Gil A, Mollinedo F, Pérez-de la Rosa F, Pérez-Roth E, Padrón JM..  (2014)  Synthesis and biological activity of polyalthenol and pentacyclindole analogues.,  73  [PMID:24412720] [10.1016/j.ejmech.2013.12.012]

Source

Source(1):

• Scientific Literature