(Z)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-octadecadi-9,12-enamide

ID: ALA1672680

Cas Number: 16729-47-8

PubChem CID: 6444746

Max Phase: Preclinical

Molecular Formula: C26H41NO3

Molecular Weight: 415.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCc1ccc(O)c(OC)c1

Standard InChI:  InChI=1S/C26H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26(29)27-22-23-19-20-24(28)25(21-23)30-2/h7-8,10-11,19-21,28H,3-6,9,12-18,22H2,1-2H3,(H,27,29)/b8-7-,11-10-

Standard InChI Key:  QLXBKYBHBQBEFT-NQLNTKRDSA-N

Molfile:  

     RDKit          2D

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   12.2732  -21.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5630  -21.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8443  -21.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1341  -21.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4155  -21.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4071  -22.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6885  -23.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6802  -23.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3904  -24.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9918  -21.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7020  -21.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1090  -23.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8193  -24.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5379  -23.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2481  -24.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9667  -23.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6770  -24.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3956  -23.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1058  -24.3958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4039  -23.1511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8244  -23.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5347  -24.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5238  -25.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2332  -25.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9527  -25.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9585  -24.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2484  -24.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6635  -25.6662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6757  -24.0104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3874  -24.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
 15 16  1  0
  5  6  1  0
 16 17  1  0
  6  7  1  0
 17 18  1  0
  7  8  2  0
 18 19  1  0
  8  9  1  0
 18 20  2  0
  1 10  1  0
 19 21  1  0
 10 11  1  0
 21 22  1  0
 22 23  2  0
  9 12  1  0
 23 24  1  0
  1  2  1  0
 24 25  2  0
 12 13  1  0
 25 26  1  0
  2  3  1  0
 26 27  2  0
 27 22  1  0
 13 14  1  0
 25 28  1  0
  3  4  1  0
 26 29  1  0
 14 15  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1672680

   9,12-Octadecadienamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-, (Z,Z)-

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: 415.62

Molecular Weight (Monoisotopic): 415.3086

AlogP: 6.83

#Rotatable Bonds: 17

Polar Surface Area: 58.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.93

CX Basic pKa: ┄

CX LogP: 7.10

CX LogD: 7.10

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.22

Np Likeness Score: 0.51

References

1. Dang HT, Kang GJ, Yoo ES, Hong J, Choi JS, Kim HS, Chung HY, Jung JH..  (2011)  Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads.,  19  (4): [PMID:21257314] [10.1016/j.bmc.2010.12.046]

2. Schiano Moriello A, López Chinarro S, Novo Fernández O, Eras J, Amodeo P, Canela-Garayoa R, Vitale RM, Di Marzo V, De Petrocellis L..  (2018)  Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists.,  61  (18): [PMID:30176215] [10.1021/acs.jmedchem.8b00734]

3. Richbart SD, Friedman JR, Brown KC, Gadepalli RS, Miles SL, Rimoldi JM, Rankin GO, Valentovic MA, Tirona MT, Finch PT, Hess JA, Dasgupta P..  (2021)  Nonpungent N-AVAM Capsaicin Analogues and Cancer Therapy.,  64  (3.0): [PMID:33508189] [10.1021/acs.jmedchem.0c01679]

Source

Source(1):

• Scientific Literature