N-(4-hydroxy-3-methoxyphenyl)icosa-5,8,11,14-tetraenamide

ID: ALA472898

Chembl Id: CHEMBL472898

PubChem CID: 25178127

Max Phase: Preclinical

Molecular Formula: C27H39NO3

Molecular Weight: 425.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)Nc1ccc(O)c(OC)c1

Standard InChI:  InChI=1S/C27H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-27(30)28-24-21-22-25(29)26(23-24)31-2/h7-8,10-11,13-14,16-17,21-23,29H,3-6,9,12,15,18-20H2,1-2H3,(H,28,30)/b8-7-,11-10-,14-13-,17-16-

Standard InChI Key:  VNIXBNUUGFHGQG-ZKWNWVNESA-N

Alternative Forms

1. Parent:

   

   ALA472898

   N-(4-hydroxy-3-methoxyphenyl)icosa-5,8,11,14-tetraenamide

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: 425.61

Molecular Weight (Monoisotopic): 425.2930

AlogP: 7.49

#Rotatable Bonds: 16

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: 9.92

CX Basic pKa: ┄

CX LogP: 7.56

CX LogD: 7.56

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.16

Np Likeness Score: 0.31

References

1. Sinning C, Watzer B, Coste O, Nüsing RM, Ott I, Ligresti A, Di Marzo V, Imming P..  (2008)  New analgesics synthetically derived from the paracetamol metabolite N-(4-hydroxyphenyl)-(5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-enamide.,  51  (24): [PMID:19053765] [10.1021/jm800807k]

2. Å Nilsson JL,Mallet C,Shionoya K,Blomgren A,Sundin AP,Grundemar L,Boudieu L,Blomqvist A,Eschalier A,Nilsson UJ,Zygmunt PM.  (2021)  Paracetamol analogues conjugated by FAAH induce TRPV1-mediated antinociception without causing acute liver toxicity.,  213  [PMID:33257173] [10.1016/j.ejmech.2020.113042]

Source

Source(1):

• Scientific Literature