Methyl aureanindol-16-ene-21-oate

ID: ALA3115633

PubChem CID: 76336031

Max Phase: Preclinical

Molecular Formula: C24H31NO2

Molecular Weight: 365.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@]1(C)CCC=C2[C@@H]1CC[C@@H](C)[C@]2(C)Cc1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C24H31NO2/c1-16-11-12-20-19(9-7-13-23(20,2)22(26)27-4)24(16,3)14-17-15-25-21-10-6-5-8-18(17)21/h5-6,8-10,15-16,20,25H,7,11-14H2,1-4H3/t16-,20+,23+,24+/m1/s1

Standard InChI Key:  NNODWARDQFGXKL-GEPCJHAKSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.1874   -5.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1874   -5.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8927   -6.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8927   -4.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4763   -7.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935   -7.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8852   -7.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1077   -7.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2907   -8.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -5.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -5.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3033   -6.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0111   -5.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101   -5.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3013   -4.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8891   -5.5016    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7177   -4.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2991   -3.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0063   -4.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9585   -3.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7309   -2.3119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9546   -2.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155   -2.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -3.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0682   -4.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8804   -4.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3589   -3.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0236   -3.0533    0.0000 C   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  2  0
  3  5  1  0
  3  6  1  1
  6  7  1  0
  6  8  2  0
  7  9  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11 16  1  1
 14 17  1  6
 15 18  1  0
 15 19  1  6
 18 20  1  0
 20 24  1  0
 23 21  1  0
 21 22  1  0
 22 20  2  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3115633

   methyl (1S,5S,6R,8aS)-5-(1H-indol-3-ylmethyl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-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: 365.52

Molecular Weight (Monoisotopic): 365.2355

AlogP: 5.66

#Rotatable Bonds: 3

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: 5.74

CX LogD: 5.74

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.56

Np Likeness Score: 1.97

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