NP-MRD: Showing NP-Card for (-)-myrtenol (NP0208781)

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Record Information

Version

2.0

Created at

2022-09-05 05:55:36 UTC

Updated at

2022-09-05 05:55:37 UTC

NP-MRD ID

NP0208781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-myrtenol

Description

(-)-Myrtenol, also known as pin-2-ene-10-ol or myrtenol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (-)-myrtenol is found in Artemisia herba-alba, Cyperus articulatus, Ips cembrae, Juniperus communis, Picea abies, Pistacia atlantica and Valeriana officinalis. (-)-myrtenol was first documented in 2022 (PMID: 35956847). Based on a literature review a small amount of articles have been published on (-)-Myrtenol (PMID: 35807301) (PMID: 35712716) (PMID: 35364892).

Structure

MOL 3D MOL SDF PDB SMILES InChI

View in JSmol

Synonyms

Value	Source
6,6-Dimethylbicyclo(3.1.1)hept-2-ene-2-methanol	MeSH
Pin-2-ene-10-ol	MeSH
6,6-Dimethyl-2-oxymethylbicyclo(1.1.3)hept-2-ene	MeSH
Myrtenol	MeSH
2-Pinen-10-ol	MeSH

Chemical Formula

C₁₀H₁₆O

Average Mass

152.2370 Da

Monoisotopic Mass

152.12012 Da

IUPAC Name

[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol

Traditional Name

[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2C[C@H]1C(CO)=CC2

InChI Identifier

InChI=1S/C10H16O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,8-9,11H,4-6H2,1-2H3/t8-,9-/m0/s1

InChI Key

RXBQNMWIQKOSCS-IUCAKERBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia herba-alba	LOTUS Database	35616633
Cyperus articulatus	LOTUS Database	35616633
Ips cembrae	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Picea abies	LOTUS Database	35616633
Pistacia atlantica	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.52	ChemAxon
pKa (Strongest Acidic)	17.1	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	1	ChemAxon
Refractivity	46.5 m³·mol⁻¹	ChemAxon
Polarizability	18.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000812

Chemspider ID

79660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

88301

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Schepetkin IA, Ozek G, Ozek T, Kirpotina LN, Khlebnikov AI, Quinn MT: Neutrophil Immunomodulatory Activity of (-)-Borneol, a Major Component of Essential Oils Extracted from Grindelia squarrosa. Molecules. 2022 Jul 31;27(15). pii: molecules27154897. doi: 10.3390/molecules27154897. [PubMed:35956847 ]
Mendes D, Branco S, Paiva MR, Schutz S, Mateus EP, Gomes da Silva M: Unveiling Chemical Cues of Insect-Tree and Insect-Insect Interactions for the Eucalyptus Weevil and Its Egg Parasitoid by Multidimensional Gas Chromatographic Methods. Molecules. 2022 Jun 23;27(13). pii: molecules27134042. doi: 10.3390/molecules27134042. [PubMed:35807301 ]
Oliveira JP, Abreu FF, Bispo JMM, Cerqueira ARA, Dos Santos JR, Correa CB, Costa SKP, Camargo EA: Myrtenol Reduces Orofacial Nociception and Inflammation in Mice Through p38-MAPK and Cytokine Inhibition. Front Pharmacol. 2022 May 30;13:910219. doi: 10.3389/fphar.2022.910219. eCollection 2022. [PubMed:35712716 ]
Neeman EM, Osseiran N, Huet TR: The conformational landscape of myrtenol: The structure of the hydroxymethyl group and its robustness upon hydration. J Chem Phys. 2022 Mar 28;156(12):124301. doi: 10.1063/5.0084562. [PubMed:35364892 ]
LOTUS database [Link]

Showing NP-Card for (-)-myrtenol (NP0208781)

MOL for NP0208781 ((-)-myrtenol)

3D MOL for NP0208781 ((-)-myrtenol)

3D SDF for NP0208781 ((-)-myrtenol)

3D-SDF for NP0208781 ((-)-myrtenol)

PDB for NP0208781 ((-)-myrtenol)

3D PDB for NP0208781 ((-)-myrtenol)

SMILES for NP0208781 ((-)-myrtenol)

INCHI for NP0208781 ((-)-myrtenol)

Structure for NP0208781 ((-)-myrtenol)

3D Structure for NP0208781 ((-)-myrtenol)