AFCDB: Nopol (FDB001291)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:54 UTC

Update date

2019-11-26 02:56:15 UTC

Primary ID

FDB001291

Secondary Accession Numbers

FDB001292

Chemical Information

FooDB Name

Nopol

Description

(-)-nopol is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other (-)-nopol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-nopol is a sweet, balsamic, and citrus tasting compound found in carrot, rosemary, and wild carrot, which makes (-)-nopol a potential biomarker for the consumption of these food products.

CAS Number

128-50-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	3.22	ALOGPS
logP	1.81	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	16.99	ChemAxon
pKa (Strongest Basic)	-1.9	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	2	ChemAxon
Refractivity	51.25 m³·mol⁻¹	ChemAxon
Polarizability	20.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H18O

IUPAC name

2-{6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}ethan-1-ol

InChI Identifier

InChI=1S/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3

InChI Key

ROKSAUSPJGWCSM-UHFFFAOYSA-N

Isomeric SMILES

CC1(C)C2CC1C(CCO)=CC2

Average Molecular Weight

166.26

Monoisotopic Molecular Weight

166.135765198

Classification

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Bicyclic monoterpenoid
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 79.47%; H 10.91%; O 9.62%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-054o-9600000000-36499504cc88c9623c93	2015-03-01	View Spectrum
Predicted GC-MS	Nopol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00s6-5900000000-d23e455893d418d01858	Spectrum
Predicted GC-MS	Nopol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9620000000-565e4a58ee8c637a6e52	Spectrum
Predicted GC-MS	Nopol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0900000000-b52f1a4c416c90f7666e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-20ad2500efd50a13fe6f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-007k-0900000000-8cedaa08b51367c120fc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-669afeea70039d5626c9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0900000000-7411e6ee830774016459	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00re-2900000000-9a3b8943337fd74831d4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-31eb65f0b47955870b8d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-b5bef5289d2fee1873b0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-dbcc9ddd2c6244883321	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-05af9fd30de6fd63473b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-a2f17ad3d8e232de73ae	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1900000000-8497c6b5069c96120315	2021-09-24	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BYY03-N:BYY03-N

EAFUS ID

1761

Dr. Duke ID

NOPOL

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1017251

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsamic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pine	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Nopol (FDB001291)

Structure for FDB001291 (Nopol)