Structure Database (LMSD)

Common Name
12-bromo-dodecanoic acid
Systematic Name
12-bromo-dodecanoic acid
Synonyms
LM ID
LMFA01090007
Formula
C12H23O2Br
Exact Mass
Calculate m/z
278.08814
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Halogenated fatty acids [FA0109]

Biological Context

12-Bromododecanoic acid is a halogenated form of lauric acid . It has been used in the synthesis of clickable forms of myristic acid and as a model fatty acid ligand to determine the X-ray crystal structure of bovine β-lactoglobulin-ligand complexes.1,2 12-Bromododecanoic acid (10 µg/ml) reduces virion DNA in the culture supernatant of primary hepatocytes isolated from a duckling model of hepatitis B virus (HBV) infection and inhibits HIV replication in CEM-SS T cells (EC50 = 38 µM).3

This information has been provided by Cayman Chemical

References

1. Heal, W.P., Wickramasinghe, S.R., Leatherbarrow, R.J., et al. N-Myristoyl transferase-mediated protein labelling in vivo. Org. Biomol. Chem. 6(13), 2308-2315 (2008).
2. Qin, B.Y., Creamer, L.K., Baker, E.N., et al. 12-Bromododecanoic acid binds inside the calyx of bovine β-lactoglobulin. FEBS Lett. 438(3), 272-278 (1998).
3. Parang, K., Wiebe, L.I., Knaus, E.E., et al. In vitro antiviral activities of myristic acid analogs against human immunodeficiency and hepatitis B viruses. Antiviral Res. 34(3), 75-90 (1997).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Imported from LIPIDAT database. Likely synthetic

String Representations

InChiKey (Click to copy)
YYKBWYBUCFHYPR-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C12H23BrO2/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h1-11H2,(H,14,15)
SMILES (Click to copy)
C(CCCCCCCCCCCBr)(=O)O

Other Databases

LIPIDAT ID
2390
CHEBI ID
49519
PubChem CID
175468
Cayman ID
30465
PDB ID
BRC

Calculated Physicochemical Properties

Heavy Atoms 15
Rings 0
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 250.38
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 4.65
Molar Refractivity 68.09

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Created at
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Updated at
14th Dec 2023