NP-MRD: Showing NP-Card for (1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol (NP0225340)

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Record Information

Version

2.0

Created at

2022-09-06 04:01:53 UTC

Updated at

2022-09-06 04:01:53 UTC

NP-MRD ID

NP0225340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

Description

Trans-Verbenol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol is found in Achillea abrotanoides, Anthemis aciphylla, Artemisia herba-alba, Artemisia judaica, Artemisia sericea, Brassica nigra, Commiphora gurreh, Echinophora tournefortii, Gutierrezia sarothrae, Helminthotheca echioides, Ips cembrae, Lavandula stoechas, Micromeria biflora, Micromeria cristata, Mosla chinensis, Myrtus communis, Peumus boldus, Pityophthorus pityographus, Stevia rebaudiana, Teucrium polium and Vitex agnus-castus. (1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol was first documented in 2021 (PMID: 33923848). Based on a literature review a small amount of articles have been published on trans-Verbenol (PMID: 35807301) (PMID: 35200079) (PMID: 34808354).

Structure

MOL 3D MOL SDF PDB SMILES InChI

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O

Average Mass

152.2370 Da

Monoisotopic Mass

152.12012 Da

IUPAC Name

(1R,2S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

Traditional Name

(1R,2S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

CAS Registry Number

Not Available

SMILES

CC1=C[C@H](O)[C@@H]2C[C@H]1C2(C)C

InChI Identifier

InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9+/m1/s1

InChI Key

WONIGEXYPVIKFS-VGMNWLOBSA-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
Achillea abrotanoides	LOTUS Database	35616633
Anthemis aciphylla	LOTUS Database	35616633
Artemisia herba-alba	LOTUS Database	35616633
Artemisia judaica	LOTUS Database	35616633
Artemisia sericea	LOTUS Database	35616633
Brassica nigra	LOTUS Database	35616633
Commiphora gurreh	LOTUS Database	35616633
Echinophora tournefortii	LOTUS Database	35616633
Gutierrezia sarothrae	LOTUS Database	35616633
Helminthia echioides	LOTUS Database	35616633
Ips cembrae	LOTUS Database	35616633
Lavandula stoechas	LOTUS Database	35616633
Micromeria biflora	LOTUS Database	35616633
Micromeria cristata	LOTUS Database	35616633
Mosla chinensis	LOTUS Database	35616633
Myrtus communis	LOTUS Database	35616633
Peumus boldus	LOTUS Database	35616633
Pityophthorus pityographus	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Vitex agnus-castus	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
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
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	1.65	ChemAxon
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	-1.2	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	0	ChemAxon
Refractivity	46.16 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

C00000863

Chemspider ID

80927

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

89664

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
Ayub MA, Hanif MA, Blanchfield J, Zubair M, Abid MA, Saleh MT: Chemical composition and antimicrobial activity of Boswellia serrata oleo-gum-resin essential oil extracted by superheated steam. Nat Prod Res. 2022 Feb 24:1-6. doi: 10.1080/14786419.2022.2044327. [PubMed:35200079 ]
Ramakrishnan R, Hradecky J, Roy A, Kalinova B, Mendezes RC, Synek J, Blaha J, Svatos A, Jirosova A: Metabolomics and transcriptomics of pheromone biosynthesis in an aggressive forest pest Ips typographus. Insect Biochem Mol Biol. 2022 Jan;140:103680. doi: 10.1016/j.ibmb.2021.103680. Epub 2021 Nov 19. [PubMed:34808354 ]
Gimenes L, Silva JCRL, Facanali R, Hantao LW, Siqueira WJ, Marques MOM: Essential Oils of New Lippia alba Genotypes Analyzed by Flow-Modulated Comprehensive Two-Dimensional Gas Chromatography (GCxGC) and Chemometric Analysis. Molecules. 2021 Apr 16;26(8):2332. doi: 10.3390/molecules26082332. [PubMed:33923848 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol (NP0225340)

MOL for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

3D MOL for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

3D SDF for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

3D-SDF for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

PDB for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

3D PDB for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

SMILES for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

INCHI for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

Structure for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)

3D Structure for NP0225340 ((1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol)