ID: ALA2415106

Max Phase: Preclinical

Molecular Formula: C25H39NO

Molecular Weight: 369.59

Molecule Type: Small molecule

Representations

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

Standard InChI:  InChI=1S/C25H39NO/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/h6-7,9-10,16-18,20-21H,2-5,8,11-15,19,22-23H2,1H3,(H,26,27)/b7-6-,10-9-

Standard InChI Key:  YJWLCIANOBCQGW-HZJYTTRNSA-N

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

Properties

Molecular Weight: 369.59

Molecular Weight (Monoisotopic): 369.3032

AlogP: 7.12

#Rotatable Bonds: 16

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: 7.56

CX LogD: 7.56

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.24

Np Likeness Score: 0.22

References

1. 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]

2. Hajdu Z, Nicolussi S, Rau M, Lorántfy L, Forgo P, Hohmann J, Csupor D, Gertsch J..  (2014)  Identification of endocannabinoid system-modulating N-alkylamides from Heliopsis helianthoides var. scabra and Lepidium meyenii.,  77  (7): [PMID:24972328] [10.1021/np500292g]

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

4. 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]

5. 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]

Source

Source(1):

• Scientific Literature