Structure Database (LMSD)
Common Name
9S,10S,13S-trihydroxyoctadec-11E-enoic acid
Systematic Name
9S,10S,13S-trihydroxy-11E-octadecenoic acid
Synonyms
- 9S,10S,13S-11E-TriHOME
LM ID
LMFA02000336
Formula
Exact Mass
Calculate m/z
330.240625
Sum Composition
Status
Curated
3D model of 9S,10S,13S-trihydroxyoctadec-11E-enoic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
9(S),10(S),13(S)-TriHOME is an oxylipin derived from linoleic acid.1,2 It has been detected in beer and in bronchoalveolar lavage fluid (BALF) from female smokers.
This information has been provided by Cayman Chemical
References
2. Hamberg, M. Trihydroxyoctadecenoic acids in beer: Qualitative and quantitative analysis. J. Agric. Food Chem. 39(9), 1568-1572 (1991).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
An LC-MS/MS workflow to characterize 16 regio- and stereoisomeric trihydroxyoctadecenoic acids.,
J Lipid Res, 2018
J Lipid Res, 2018
Pubmed ID:
30065010
DOI:
10.1194/jlr.D087429
String Representations
InChiKey (Click to copy)
NTVFQBIHLSPEGQ-MVFSOIOZSA-N
InChi (Click to copy)
InChI=1S/C18H34O5/c1-2-3-7-10-15(19)13-14-17(21)16(20)11-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1
SMILES (Click to copy)
C(C)CCC[C@H](O)/C=C/[C@H](O)[C@@H](O)CCCCCCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
358.63
Topological Polar Surface Area
97.99
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
5
logP
3.88
Molar Refractivity
92.79
Admin
Created at
-
Updated at
-