NP-MRD: Showing NP-Card for 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol (NP0044924)

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Record Information

Version

2.0

Created at

2022-03-10 18:51:12 UTC

Updated at

2022-03-10 22:16:45 UTC

NP-MRD ID

NP0044924

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol

Description

Fenchol or 1,3,3-Trimethylbicyclo[2.2.1]Heptan-2-ol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Fenchol is a naturally occurring bicyclic monoterpenoid and an isomer of Borneol. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclation reactions to yield a diverse number of cyclic arrangements. Fenchol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a colorless or white solid with a characteristic scent found in basil and Aster and cannabis plants (PMID:6991645 ). Fenchol is used extensively in perfumery.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    2.3565   -0.1274   -0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1182   -0.0480    0.1365 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5473   -0.3111    1.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638   -1.0691   -0.3149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0700   -2.1074    0.5657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616   -0.2075   -0.4520 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2740   -0.7965   -1.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5382    0.4144    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.4903    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4780    1.2992   -0.0156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5303    1.0154   -1.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536    0.8732   -1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682   -0.3673   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845   -0.8843   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7334   -0.6456    2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369    0.6206    1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444   -1.0921    1.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3679   -1.3676   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1080   -2.9610    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2434   -0.5169   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3012   -0.3968   -2.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220   -1.9136   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6048   -0.2989    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115    0.9350    0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097    1.3089    2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973    2.5059    1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1324    2.1213   -0.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0402    0.7441   -2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2998    1.7830   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  6
  6 11  1  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
 11 10  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
 10 27  1  6
  9 25  1  0
  9 26  1  0
  8 23  1  0
  8 24  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
 11 28  1  0
 11 29  1  0
  4 18  1  6
  5 19  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1S,2-endo)-1,3,3-Trimethylnorbornan-2-ol	ChEBI
(1S,2S,4R)-endo-Fenchol	ChEBI
1,3,3-Trimethyl-2-norbornanol	ChEBI
2-Fenchanol	ChEBI
alpha-Fenchol	ChEBI
alpha-Fenchyl alcohol	ChEBI
endo-alpha-Fenchol	ChEBI
endo-Fenchol	ChEBI
Fenchyl alcohol	ChEBI
(-)-alpha-Fenchyl alcohol	Kegg
a-Fenchol	Generator
Α-fenchol	Generator
a-Fenchyl alcohol	Generator
Α-fenchyl alcohol	Generator
endo-a-Fenchol	Generator
endo-Α-fenchol	Generator
(-)-a-Fenchyl alcohol	Generator
(-)-Α-fenchyl alcohol	Generator
a-Fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol	Generator
Α-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol	Generator
Fenchol, ((endo)-(+-))-isomer	MeSH
Fenchol, ((exo)-(+-))-isomer	MeSH
Fenchol, (endo)-isomer	MeSH
Fenchol, (1R-endo)-isomer	MeSH
Fenchol, (1S-exo)-isomer	MeSH
Fenchol	MeSH
Fenchol, (1S-endo)-isomer	MeSH
Fenchol, (exo)-isomer	MeSH
(1S,2S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol	PhytoBank
(-)-endo-Fenchol	PhytoBank
(-)-alpha-Fenchol	PhytoBank
(-)-α-Fenchol	PhytoBank
(1S-endo)-Fenchol	PhytoBank
l-alpha-Fenchyl alcohol	PhytoBank
l-α-Fenchyl alcohol	PhytoBank
rel-(1R,2R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol	PhytoBank
(±)-alpha-Fenchol	PhytoBank
(±)-α-Fenchol	PhytoBank
dl-alpha-Fenchol	PhytoBank
dl-α-Fenchol	PhytoBank
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol	PhytoBank

Chemical Formula

C₁₀H₁₈O

Average Mass

154.2530 Da

Monoisotopic Mass

154.13577 Da

IUPAC Name

(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol

Traditional Name

((endo)-(+-))-fenchol

CAS Registry Number

2217-02-9

SMILES

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

InChI Identifier

InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1

InChI Key

IAIHUHQCLTYTSF-MRTMQBJTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Abies sibirica	LOTUS Database	35616633
Alpinia zerumbet	LOTUS Database	35616633
Artemisia annua	LOTUS Database	35616633
Artemisia tridentata	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Calyptranthes spruceana	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Cistus incanus	LOTUS Database	35616633
Citrus iyo	LOTUS Database	35616633
Cleonia lusitanica	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Curcuma pierreana	LOTUS Database	35616633
Cyperus rotundus	LOTUS Database	35616633
Eucalyptus melanophloia	LOTUS Database	35616633
Eucalyptus moluccana	LOTUS Database	35616633
Eucalyptus nitens	LOTUS Database	35616633
Eucalyptus tetraptera	LOTUS Database	35616633
Ferula assa-foetida	LOTUS Database	35616633
Ferula ovina	LOTUS Database	35616633
Foeniculum vulgare	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Helichrysum odoratissimum	LOTUS Database	35616633
Hyptis goyazensis	LOTUS Database	35616633
Kunzea salina	LOTUS Database	35616633
Liquidambar styraciflua	LOTUS Database	35616633
Myrcianthes fragrans	LOTUS Database	35616633
Myrtus communis	LOTUS Database	35616633
Picea abies	LOTUS Database	35616633
Salvia rosmarinus	LOTUS Database	35616633
Sequoiadendron giganteum	LOTUS Database	35616633
Sideritis leucantha	LOTUS Database	35616633
Sideritis tragoriganum	LOTUS Database	35616633
Stoebe plumosa	LOTUS Database	35616633
Zanthoxylum armatum	LOTUS Database	35616633
Zingiber mioga	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

Fenchane monoterpenoid
Bicyclic monoterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

carbobicyclic compound (CHEBI:15405 )
fenchane monoterpenoid (CHEBI:15405 )
Bicyclic monoterpenoids (LMPR0102120005 )

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	2.3	ALOGPS
logP	2.15	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-0.52	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	45.16 m³·mol⁻¹	ChemAxon
Polarizability	18.52 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

FDB029688

KNApSAcK ID

C00035801

Chemspider ID

Not Available

KEGG Compound ID

C02344

BioCyc ID

CPD-685

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439711

PDB ID

Not Available

ChEBI ID

15405

Good Scents ID

Not Available

References

General References

Padalia RC, Chanotiya CS, Sundaresan V: Compositional variability in essential oil from different parts of Alpinia speciosa from India. Nat Prod Commun. 2010 Feb;5(2):279-82. [PubMed:20334144 ]
Koksal M, Chou WK, Cane DE, Christianson DW: Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate. Biochemistry. 2012 Apr 10;51(14):3011-20. doi: 10.1021/bi201827a. Epub 2012 Mar 28. [PubMed:22455514 ]

Showing NP-Card for 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol (NP0044924)

MOL for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

3D MOL for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

3D SDF for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

3D-SDF for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

PDB for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

3D PDB for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

SMILES for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

INCHI for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

Structure for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)

3D Structure for NP0044924 (1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol)