Structure Database (LMSD)
Common Name
10-hydroxy-2E-decenoic acid
Systematic Name
10-hydroxy-2E-decenoic acid
Synonyms
3D model of 10-hydroxy-2E-decenoic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
10-HDA is an unsaturated fatty acid found in royal jelly produced from the hypopharyngeal and mandibular gland secretions of honeybees.1 10-HDA has longevity-promoting effects in C. elegans at a concentration of 25 μM.2 It down-regulates matrix metalloproteinases (MMPs) in rheumatoid arthritis synovial fibroblasts at a concentration of 1.25 nM and inhibits VEGF-induced angiogenesis in HUVECs at 500 μM.3,4 10-HDA also facilitates differentiation of neurons from neural stem/progenitor cells and promotes collagen production by skin fibroblasts at concentrations of 100 μM and 1.5 mM, respectively.5,6
This information has been provided by Cayman Chemical
References
2. Kodai, T., Umebayashi, K., Nakatani, T., et al. Compositions of royal jelly II. Organic acid glycosides and sterols of the royal jelly of honeybees (Apis mellifera). Chem. Pharm. Bull. (Tokyo) 55(10), 1528-1531 (2007).
3. Izuta, H., Chikaraishi, Y., Shimazawa, M., et al. 10-Hydroxy-2-decenoic acid, a major fatty acid from royal jelly, inhibits VEGF-induced angiogenesis in human umbilical vein endothelial cells. Evid. Based Complement. Alternat. Med. 6(4), 489-494 (2009).
String Representations
InChiKey (Click to copy)
QHBZHVUGQROELI-SOFGYWHQSA-N
InChi (Click to copy)
InChI=1S/C10H18O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h6,8,11H,1-5,7,9H2,(H,12,13)/b8-6+
SMILES (Click to copy)
C(/C=C/CCCCCCCO)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
13
Rings
0
Aromatic Rings
0
Rotatable Bonds
8
Van der Waals Molecular Volume
202.65
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
2.24
Molar Refractivity
52.05
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Updated at
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