N-allyl-tabernaemontanine

ID: ALA4742984

PubChem CID: 162646408

Max Phase: Preclinical

Molecular Formula: C24H30N2O3

Molecular Weight: 394.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CCn1c2c(c3ccccc31)C[C@H]1C(C(=O)OC)[C@H](CC2=O)[C@H](CC)CN1C

Standard InChI:  InChI=1S/C24H30N2O3/c1-5-11-26-19-10-8-7-9-16(19)18-12-20-22(24(28)29-4)17(13-21(27)23(18)26)15(6-2)14-25(20)3/h5,7-10,15,17,20,22H,1,6,11-14H2,2-4H3/t15-,17-,20+,22?/m1/s1

Standard InChI Key:  SLPISKNXJKWBMN-LBXXQKFWSA-N

Molfile:  

 
     RDKit          2D

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    8.9324   -7.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9313   -8.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6451   -9.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3580   -8.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1474   -8.9844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1490   -7.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6389   -8.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4782   -6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7935   -7.4649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4580   -8.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.7670   -8.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1024   -8.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6145   -7.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0380   -8.9339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.2517   -9.4682    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3807   -5.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1766   -5.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1675   -4.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7591   -5.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3073   -6.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7982   -6.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3002   -5.9753    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9217   -7.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4067   -8.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4012   -9.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8492  -10.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1029  -11.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
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  4  1  1  0
  5  6  1  0
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  8  9  2  0
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  9 12  1  0
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 24 10  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 17  2  0
 11 18  1  0
 14 19  1  6
 25 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 14 25  1  0
 25 24  1  0
 24 26  1  6
 15 27  1  1
 27 28  1  0
  7 29  1  0
 29 30  1  0
 30 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4742984

   ---

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: 394.52

Molecular Weight (Monoisotopic): 394.2256

AlogP: 3.70

#Rotatable Bonds: 4

Polar Surface Area: 51.54

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.60

CX LogP: 3.61

CX LogD: 3.20

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: 0.71

References

1. Cardoso DSP,Kincses A,Nové M,Spengler G,Mulhovo S,Aires-de-Sousa J,Dos Santos DJVA,Ferreira MU.  (2021)  Alkylated monoterpene indole alkaloid derivatives as potent P-glycoprotein inhibitors in resistant cancer cells.,  210  [PMID:33189435] [10.1016/j.ejmech.2020.112985]

Source

Source(1):

• Scientific Literature