Structure Database (LMSD)

Common Name
Margaroleic acid
Systematic Name
9Z-heptadecenoic acid
Synonyms
  • cis-9-heptadecenoic acid
  • C17:1n-8
  • 9-heptadecylenic acid
LM ID
LMFA01030060
Formula
C17H32O2
Exact Mass
Calculate m/z
268.24023
Sum Composition
FA 17:1
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 Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

cis-9-Heptadecenoic acid is a monounsaturated fatty acid that is a major constituent of ruminant fat and milk.1 The levels of cis-9-heptadecenoic acid in milk are negatively correlated with methane production in cows fed a high-lipid diet.2

This information has been provided by Cayman Chemical

References

1. Dijkstra, J., van Zijderveld, S.M., Apajalahti, J.A., et al. Relationships between methane production and milk fatty acid profiles in dairy cattle. Anim. Feed Sci. Technol. 166-167, 23 (2011).
2. Alves, S.P., Marcelino, C., Portugal, P.V., et al. Short communication: The nature of heptadecenoic acid in ruminant fats. J. Dairy Sci. 89(1), 170-173 (2006).

Reactions

Filter by species:
ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Bos taurus (#9913)
Mammalia (#40674)
Isolation of cis-delta-9 heptadecenoic acid from butterfat,
Biochem J, 1960

String Representations

InChiKey (Click to copy)
QSBYPNXLFMSGKH-HJWRWDBZSA-N
InChi (Click to copy)
InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h8-9H,2-7,10-16H2,1H3,(H,18,19)/b9-8-
SMILES (Click to copy)
C(CCCCCCC(=O)O)/C=C\CCCCCCC

Other Databases

KEGG ID
C16536
HMDB ID
HMDB0062437
CHEBI ID
84328
LIPIDBANK ID
DFA0099
PubChem CID
5282748
PlantFA ID
10364
Cayman ID
36254

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 314.96
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.72
Molar Refractivity 82.47

Admin

Created at
-
Updated at
25th Apr 2022