LIPID MAPS

Structure Database (LMSD)

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Common Name

Macamide

Systematic Name

N-hexadecanoyl benzylamine

Synonyms

N-benzylpalmitamide

LM ID

LMFA08020155

Formula

C₂₃H₃₉NO

Exact Mass

Calculate m/z

345.303164

Sum Composition

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Category

Main Class

Sub Class

Fatty Acyls [FA]

Fatty amides [FA08]

N-acyl amines [FA0802]

Fatty Acids and Conjugates [FA01]

Unsaturated fatty acids [FA0103]

Carbocyclic fatty acids [FA0114]

Biological Context

N-Benzylpalmitamide is a long-chain fatty acid amide (macamide or macaene) isolated from the maca (L. meyenii) plant and is structurally related to cannabinoids.¹ N-Benzylpalmitamide has been the most frequently isolated of the 19 macamides currently identified. While many macamides have been identified as potent inhibitors of fatty acid amide hydrolase (FAAH), N-benzylpalmitamide displays only moderate FAAH inhibitory activity (44% inhibition at 500 µM).¹ Additionally, many members of this family demonstrate selective antiproliferative activity against diverse cancer cell lines.²

This information has been provided by Cayman Chemical

References

1. Wu, H., Kelley, C.J., Pino-Figueroa, A., et al. Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition. Bioorg. Med. Chem. 21(17), 5188-5197 (2013).

2. dos Santos, D.S., Piovesan, L.A., D'Oca, C.R.M., et al. Antiproliferative activity of synthetic fatty acid amides from renewable resources. Bioorg. Med. Chem. 23(2), 340-347 (2015).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Lepidium meyenii (#153348)

Magnoliopsida (#3398)

Constituents of Lepidium meyenii 'maca'.,
Phytochemistry, 2002

Pubmed ID: 11754952

DOI: 10.1016/s0031-9422(01)00395-8

String Representations

InChiKey (Click to copy)

MLGPKWUKOQAAGI-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C23H39NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-23(25)24-21-22-18-15-14-16-19-22/h14-16,18-19H,2-13,17,20-21H2,1H3,(H,24,25)

SMILES (Click to copy)

C(CCCCCCCCCCCCCCC)(=O)NCC1C=CC=CC=1

Other Databases

HMDB ID

CHEBI ID

PubChem CID

Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 25

Rings 1

Aromatic Rings 1

Rotatable Bonds 16

Van der Waals Molecular Volume 392.43

Topological Polar Surface Area 29.10

Hydrogen Bond Donors 1

Hydrogen Bond Acceptors 2

logP 6.78

Molar Refractivity 108.60

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Created at

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Updated at

16th Dec 2020