(4aR,6aR,12bS)-4,4,6a,12b-Tetramethyl-1,4a,5,6,6a,12,12a,12b-octahydro-2H,4H-6b-aza-benzo[5,6]pentaleno[2,1-b]naphthalen-3-one

ID: ALA1082691

PubChem CID: 46891410

Max Phase: Preclinical

Molecular Formula: C23H29NO

Molecular Weight: 335.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C(=O)CC[C@]2(C)C3Cc4cc5ccccc5n4[C@]3(C)CC[C@@H]12

Standard InChI:  InChI=1S/C23H29NO/c1-21(2)18-9-12-23(4)19(22(18,3)11-10-20(21)25)14-16-13-15-7-5-6-8-17(15)24(16)23/h5-8,13,18-19H,9-12,14H2,1-4H3/t18-,19?,22-,23+/m0/s1

Standard InChI Key:  NEPLKJAINOWIJL-IZZOUOQSSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   -1.8483    0.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8444    0.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1299   -0.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1384    1.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235    0.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180    0.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0092    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839    1.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    0.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506    2.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758    2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113    1.5438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889    2.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4341    1.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0458    1.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8330    1.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0025    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3883    2.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579   -0.2693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5469   -0.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    1.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876    1.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4200   -0.6649    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9176   -1.0500    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  6  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 11  9  1  0
 12 13  1  0
 13 16  1  0
 15 14  1  0
 14 12  2  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  2 21  2  0
  3 22  1  0
  5 23  1  1
 10 24  1  1
  6 25  1  6
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1082691

   (1R,13S,18R)-1,13,17,17-tetramethyl-2-azapentacyclo[10.8.0.02,10.03,8.013,18]icosa-3,5,7,9-tetraen-16-one

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: 335.49

Molecular Weight (Monoisotopic): 335.2249

AlogP: 5.33

#Rotatable Bonds: ┄

Polar Surface Area: 22.00

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.33

CX LogD: 5.33

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.64

Np Likeness Score: 1.46

References

1. Ngantchou I, Nyasse B, Denier C, Blonski C, Hannaert V, Schneider B..  (2010)  Antitrypanosomal alkaloids from Polyalthia suaveolens (Annonaceae): their effects on three selected glycolytic enzymes of Trypanosoma brucei.,  20  (12): [PMID:20529682] [10.1016/j.bmcl.2010.04.145]

Source

Source(1):

• Scientific Literature