N-(3-nitrobenzyl)-tabernaemontanine

ID: ALA4757834

PubChem CID: 162656119

Max Phase: Preclinical

Molecular Formula: C28H31N3O5

Molecular Weight: 489.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@@H]1CN(C)[C@H]2Cc3c(n(Cc4cccc([N+](=O)[O-])c4)c4ccccc34)C(=O)C[C@H]1C2C(=O)OC

Standard InChI:  InChI=1S/C28H31N3O5/c1-4-18-16-29(2)24-13-22-20-10-5-6-11-23(20)30(15-17-8-7-9-19(12-17)31(34)35)27(22)25(32)14-21(18)26(24)28(33)36-3/h5-12,18,21,24,26H,4,13-16H2,1-3H3/t18-,21-,24+,26?/m1/s1

Standard InChI Key:  OKFKLMDUQSONRL-PWPNFUGASA-N

Molfile:  

 
     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
    0.6065   -3.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -3.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3197   -4.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -2.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328   -3.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0330   -3.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8230   -4.2395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246   -2.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -3.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1540   -2.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4702   -2.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1345   -3.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6205   -4.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4445   -4.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7800   -3.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -2.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7142   -4.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8760   -1.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9294   -4.7236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585   -0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8549   -0.9753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8451    0.0344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4379   -0.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9837   -2.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755   -1.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9765   -1.2283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5998   -3.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0852   -3.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -5.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245   -5.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7203   -5.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -6.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219   -6.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2329   -7.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814   -6.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -7.8096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2907   -7.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9357   -8.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  8 10  1  0
  9 12  1  0
 11 24  1  0
 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
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 34 36  1  0
 36 37  2  0
 36 38  1  0
M  CHG  2  36   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4757834

   ---

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: 489.57

Molecular Weight (Monoisotopic): 489.2264

AlogP: 4.47

#Rotatable Bonds: 5

Polar Surface Area: 94.68

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.58

CX LogP: 4.55

CX LogD: 4.15

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.30

Np Likeness Score: 0.06

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