3alpha-Cinnamoyloxy-N-(3-(4-hydroxyphenyl)propanoyl)nortropane

ID: ALA5069926

PubChem CID: 166625706

Max Phase: Preclinical

Molecular Formula: C25H27NO4

Molecular Weight: 405.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1)OC1CC2CCC(C1)N2C(=O)CCc1ccc(O)cc1

Standard InChI:  InChI=1S/C25H27NO4/c27-22-12-6-19(7-13-22)8-14-24(28)26-20-10-11-21(26)17-23(16-20)30-25(29)15-9-18-4-2-1-3-5-18/h1-7,9,12-13,15,20-21,23,27H,8,10-11,14,16-17H2/b15-9+

Standard InChI Key:  FPAPOJFPIYGOGV-OQLLNIDSSA-N

Molfile:  

 
     RDKit          2D

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   20.8890   -6.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9637   -7.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4440   -6.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4677   -6.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3292   -6.1211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8224   -6.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3326   -7.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8555   -7.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9569   -8.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6611   -8.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6543   -9.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3722   -8.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0765   -8.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7876   -8.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4890   -8.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1996   -8.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2069   -7.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4977   -6.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7900   -7.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9126   -5.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3131   -4.7058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0954   -5.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6949   -6.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8777   -6.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4635   -5.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6471   -5.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2458   -6.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6668   -6.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4818   -6.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4286   -6.1793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  0
  6  2  1  0
  4  7  1  0
  1  8  1  0
  7  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  5 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5069926

   ---

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: 405.49

Molecular Weight (Monoisotopic): 405.1940

AlogP: 4.10

#Rotatable Bonds: 6

Polar Surface Area: 66.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.51

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: 0.48

References

1. Chan ZY, Krishnan P, Modaresi SM, Hii LW, Mai CW, Lim WM, Leong CO, Low YY, Wong SK, Yong KT, Leong AZ, Lee MK, Ting KN, Lim KH..  (2021)  Monomeric, Dimeric, and Trimeric Tropane Alkaloids from Pellacalyx saccardianus.,  84  (8.0): [PMID:34342431] [10.1021/acs.jnatprod.1c00374]

Source

Source(1):

• Scientific Literature