N-benzyl-9-Z-octadecenamide

ID: ALA1223510

Chembl Id: CHEMBL1223510

Cas Number: 101762-87-2

PubChem CID: 49865534

Max Phase: Preclinical

Molecular Formula: C25H41NO

Molecular Weight: 371.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC/C=C\CCCCCCCC(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C25H41NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-25(27)26-23-24-20-17-16-18-21-24/h9-10,16-18,20-21H,2-8,11-15,19,22-23H2,1H3,(H,26,27)/b10-9-

Standard InChI Key:  QHXGFOCPQQADIF-KTKRTIGZSA-N

Alternative Forms

1. Parent:

   

   ALA1223510

   N-benzyloleamide

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: 371.61

Molecular Weight (Monoisotopic): 371.3188

AlogP: 7.34

#Rotatable Bonds: 17

Polar Surface Area: 29.10

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.93

CX LogD: 7.93

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.23

Np Likeness Score: -0.02

References

1. D'Oca Cda R, Coelho T, Marinho TG, Hack CR, Duarte Rda C, da Silva PA, D'Oca MG..  (2010)  Synthesis and antituberculosis activity of new fatty acid amides.,  20  (17): [PMID:20667727] [10.1016/j.bmcl.2010.06.149]

2. Wu H, Kelley CJ, Pino-Figueroa A, Vu HD, Maher TJ..  (2013)  Macamides and their synthetic analogs: evaluation of in vitro FAAH inhibition.,  21  (17): [PMID:23891163] [10.1016/j.bmc.2013.06.034]

3. dos Santos DS, Piovesan LA, D'Oca CR, Hack CR, Treptow TG, Rodrigues MO, Vendramini-Costa DB, Ruiz AL, de Carvalho JE, D'Oca MG..  (2015)  Antiproliferative activity of synthetic fatty acid amides from renewable resources.,  23  (2): [PMID:25510639] [10.1016/j.bmc.2014.11.019]

4. Cunningham CW..  (2019)  Plant-Based Modulators of Endocannabinoid Signaling.,  82  (3): [PMID:30816712] [10.1021/acs.jnatprod.8b00874]

5. Singh N,Barnych B,Morisseau C,Wagner KM,Wan D,Takeshita A,Pham H,Xu T,Dandekar A,Liu JY,Hammock BD.  (2020)  N-Benzyl-linoleamide, a Constituent of Lepidium meyenii (Maca), Is an Orally Bioavailable Soluble Epoxide Hydrolase Inhibitor That Alleviates Inflammatory Pain.,  83  (12): [PMID:33320645] [10.1021/acs.jnatprod.0c00938]

6. Tena Perez, Victor, Apaza Ticona, Luis, Serban, Andreea Madalina, Acero Gomez, Javier, Rumbero SAnchez, Angel.  (2020)  Synthesis and biological screening of a library of macamides as TNF-alpha inhibitors,  11  (10): [PMID:33479624] [10.1039/d0md00208a]

7. Halder S, Macatangay NJ, Zerfas BL, Salazar-Chaparro AF, Trader DJ..  (2022)  Oleic amide derivatives as small molecule stimulators of the human proteasome's core particle.,  13  (9.0): [PMID:36324496] [10.1039/d2md00133k]

Source

Source(1):

• Scientific Literature