ChemFOnt: Showing chemical card for Nerolidiol (CFc000334238)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:15:10 UTC

Chemfont ID

CFc000334238

Molecule Identification

Common Name

Nerolidiol

Definition

Nerolidol also known as peruviol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Nerolidol is a naturally occurring sesquiterpene alcohol found in the essential oils of many types of plants and flowers. It is present in neroli, ginger, jasmine, lavender, tea tree, and lemon grass, and is a dominant scent compound in Brassavola nodosa. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also used in non-cosmetic products such as detergents and cleansers (PMID: 27136520 ). Currently it is also under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs (https://doi.org/10.1016/S0939-6411(01)00166-7). Additionally, it is known for various biological activities include antioxidant, anti-fungal, anticancer, and antimicrobial activity (PMID: 27136520 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3S,6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	ChEBI
(S)-cis-Nerolidol	ChEBI
(+)-cis-Nerolidol	HMDB
(+)-Nerolidol	HMDB
(6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	HMDB
(Z)-(S)-(+)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	HMDB
(Z)-Nerolidol	HMDB
3,7,11-Trimethyl-(3S,6Z)-(+)-1,6,10-dodecatrien-3-ol	HMDB
3,7,11-Trimethyl-(Z)-(S)-(+)-1,6,10-dodecatrien-3-ol	HMDB
D-Nerolidol	HMDB
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	HMDB
Nerolidol, (Z)-isomer	HMDB
Nerolidol, (S-(Z))-isomer	HMDB
Nerolidol	HMDB
Nerolidol, (e)-isomer	HMDB
Nerolidol, (S-(e))-isomer	HMDB
Peruviol	HMDB
[S-(Z)]-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	PhytoBank
folic alcohol	PhytoBank
cis-(+)-Nerolidol	PhytoBank
(3S,6Z)-Nerolidol	PhytoBank
(±)-Nerolidol	PhytoBank
Nerodilol	PhytoBank

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

(3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol

Traditional Name

(3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol

CAS Registry Number

142-50-7

SMILES

CC(C)=CCC\C(C)=C/CC[C@](C)(O)C=C

InChI Identifier

InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-/t15-/m1/s1

InChI Key

FQTLCLSUCSAZDY-QKXCFHHRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035663)

Source

Endogenous

Endogenous (HMDB: HMDB0035663)

Plant

Plant (HMDB: HMDB0035663)

Animal

Animal (HMDB: HMDB0035663)

Exogenous

Food

Food (HMDB: HMDB0035663)

Fruit

Tropical fruit

Guava (FooDB: FOOD00150)

Herb and spice

Herb

Sweet basil (FooDB: FOOD00119)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035663)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035663)

Lipid metabolism pathway (HMDB: HMDB0035663)

Cellular process

Cell signaling (HMDB: HMDB0035663)

Biochemical process

Lipid transport (HMDB: HMDB0035663)

Role

Biological role

Energy source (HMDB: HMDB0035663)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035663)

Fragrance (HMDB: HMDB0035663)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0035663)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	4.55	ALOGPS
logP	4.31	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.46	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.01 m³·mol⁻¹	ChemAxon
Polarizability	27.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035663

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006275

KNApSAcK ID

C00034757

Chemspider ID

4512192

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5356544

PDB ID

Not Available

ChEBI ID

176337

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Nerolidiol (CFc000334238)

MOL for CFc000334238 (Nerolidiol)

3D MOL for CFc000334238 (Nerolidiol)

3D SDF for CFc000334238 (Nerolidiol)

3D-SDF for CFc000334238 (Nerolidiol)

PDB for CFc000334238 (Nerolidiol)

3D PDB for CFc000334238 (Nerolidiol)

SMILES for CFc000334238 (Nerolidiol)

INCHI for CFc000334238 (Nerolidiol)

Structure for CFc000334238 (Nerolidiol)

3D Structure for CFc000334238 (Nerolidiol)