Structure Database (LMSD)

Common Name
Nerol
Systematic Name
Z-Geraniol
Synonyms
  • (Z)-Geraniol
  • (Z)-3,7-dimethylocta-2,6-dien-1-ol
  • Neryl alcohol
LM ID
LMPR0102010010
Formula
C10H18O
Exact Mass
Calculate m/z
154.135765
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C10 isoprenoids (monoterpenes) [PR0102]
Acyclic monoterpenoids [PR010201]

Biological Context

Nerol is a monoterpene and isomer of geraniol that has been found in a variety of plants, including Cannabis.1 It increases production of reactive oxygen species (ROS) and intracellular calcium levels and induces mitochondrial dysfunction, cytochrome C release, and apoptosis in A. flavus.2 Nerol (30-300 mg/kg) reduces weight loss, production of the inflammatory cytokines IL-13 and TNF-α, gastric damage, and hyperalgesia in a mouse model of oxazolone-induced colitis.3

This information has been provided by Cayman Chemical

References

1. Elzinga, S., Fischedick, J., Podkolinski, R., et al. Cannabinoids and terpenes as chemotaxonomic markers in Cannabis. Nat. Prod. Chem. Res. 3(4), 181 (2015).
2. Tian, J., Gan, Y., Pan, C., et al. Nerol-induced apoptosis associated with the generation of ROS and Ca2+ overload in saprotrophic fungus Aspergillus flavus. Appl. Microbiol. Biotechnol. 102(15), 6659-6672 (2018).
3. González-Ramírez, A.E., González-Trujano, M.E., Orozco-Suárez, S.A., et al. Nerol alleviates pathologic markers in the oxazolone-induced colitis model. Eur. J. Pharmacol. 776, 81-89 (2016).

String Representations

InChiKey (Click to copy)
GLZPCOQZEFWAFX-YFHOEESVSA-N
InChi (Click to copy)
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7-
SMILES (Click to copy)
C(/C)(=C\CO)\CC/C=C(\C)/C

Other Databases

Wikipedia
Nerol
KEGG ID
C09871
HMDB ID
HMDB0005812
CHEBI ID
29452
PubChem CID
643820
Cayman ID
25774
PDB ID
NZZ

Calculated Physicochemical Properties

Heavy Atoms 11
Rings 0
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 185.07
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 2.96
Molar Refractivity 50.00

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Updated at
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