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Showing NP-Card for (-)-borneol (NP0307913)

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Record Information
Version2.0
Created at2022-09-11 01:21:49 UTC
Updated at2022-09-11 01:21:49 UTC
NP-MRD IDNP0307913
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-borneol
Description(-)-Borneol, also known as L-borneol or linderol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other (-)-Borneol is an extremely weak basic (essentially neutral) compound (based on its pKa) (-)-Borneol is a camphor, pine, and woody tasting compound. Outside of the human body, (-)-Borneol has been detected, but not quantified in, several different foods, such as common thymes, corianders, cornmints, and tea. (-)-borneol is found in Abies sachalinensis, Abies sibirica, Ageratum conyzoides, Larix gmelinii, Mosla chinensis, Pimpinella anisum, Pinus mugo, Thymus marschallianus and Vaccinium vitis-idaea. (-)-borneol was first documented in 2010 (PMID: 20038111). This could make (-)-borneol a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0307913 ((-)-borneol)


  Mrv0541 02241214342D          

 11 12  0  0  0  0            999 V2000
   -0.1254    0.6996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8399    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254   -0.9504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5890   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890    0.2871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1254    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3035    0.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863   -0.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832    0.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  6  8  1  6  0  0  0
  1  9  1  1  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0307913 ((-)-borneol)

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    1.5547    1.1009    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8633   -0.1431    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -1.3317    0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -0.1891   -1.2530 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1562   -1.3360   -1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1974   -1.1068   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6183   -0.0115    0.5021 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0691   -0.0256    1.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    1.2890   -0.2434 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2136    1.4147   -0.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462    1.0799   -1.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    1.4894    1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662    1.8621   -0.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5823    0.8618    1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3866   -2.2754    0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6088   -1.1449    0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1907   -1.5238    1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7150   -0.2135   -1.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246   -1.2642   -2.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3022   -2.3259   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087   -0.7259   -0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261   -2.0189    0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141    1.0179    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271   -0.4219    1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4976   -0.6245    2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.1561    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443    1.6212   -1.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898    0.8549   -2.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793    1.9349   -1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
  9 11  1  0
  7  2  1  0
 11  4  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
  4 18  1  6
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  1
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for NP0307913 ((-)-borneol)


  Mrv0541 02241214342D          

 11 12  0  0  0  0            999 V2000
   -0.1254    0.6996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8399    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254   -0.9504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5890   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890    0.2871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1254    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3035    0.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863   -0.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832    0.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007   -0.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  6  8  1  6  0  0  0
  1  9  1  1  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307913

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m0/s1

> <INCHI_KEY>
DTGKSKDOIYIVQL-QXFUBDJGSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.47619618261634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
1.9894578843333337

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.60482336496175

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7846502601657298

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
45.314299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-borneol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0307913 ((-)-borneol)

Download
PDB for NP0307913 ((-)-borneol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.234   1.306   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.568   0.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.568  -1.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.234  -1.774   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.099  -1.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.099   0.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.234   2.846   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.433   1.306   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.908  -0.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.395   0.272   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.241  -0.897   0.000  0.00  0.00           C+0
CONECT    1    2    6    7    9                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    8                                                  
CONECT    7    1                                                            
CONECT    8    6                                                            
CONECT    9    1    4   10   11                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0307913 ((-)-borneol)
Download
SMILES for NP0307913 ((-)-borneol)
CC1(C)[C@H]2CC[C@]1(C)[C@H](O)C2
Download
INCHI for NP0307913 ((-)-borneol)
InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m0/s1
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View in JSmol
Synonyms
ValueSource
(1S,2R,4S)-(-)-BorneolChEBI
(1S,2R,4S)-BorneolChEBI
(1S-endo)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-olChEBI
L-BorneolChEBI
LinderolChEBI
1,7,7-Trimethyl-(1R,2S,4R)-rel-bicyclo[2.2.1]heptan-2-olHMDB
1,7,7-Trimethyl-endo-bicyclo[2.2.1]heptan-2-olHMDB
Borneo camphorHMDB
BorneolHMDB
Borneol (8ci)HMDB
Bornyl alcoholHMDB
DL-BorneolHMDB
endo-(-)-Bornan-2-olHMDB
endo-2-BornanolHMDB
endo-2-CamphanolHMDB
endo-2-Hydroxy-1,7,7-trimethylnorbornaneHMDB
endo-2-HydroxycamphaneHMDB
endo-BorneolHMDB
Rel-(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-olHMDB
Sumatra camphorHMDB
IsoborneolHMDB
Isoborneol, (1R-endo)-isomerHMDB
Isoborneol, (1S-endo)-isomerHMDB
Isoborneol, (1S-exo)-isomerHMDB
Isoborneol, (1R-exo)-isomerHMDB
Isoborneol, (endo)-isomerHMDB
Isoborneol, (endo-(+-))-isomerHMDB
Isoborneol, (exo)-isomerHMDB
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional NameL-borneol
CAS Registry NumberNot Available
SMILES
CC1(C)[C@H]2CC[C@]1(C)[C@H](O)C2
InChI Identifier
InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m0/s1
InChI KeyDTGKSKDOIYIVQL-QXFUBDJGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies sachalinensisLOTUS Database
Abies sibiricaLOTUS Database
Ageratum conyzoidesLOTUS Database
Larix gmeliniLOTUS Database
Mosla chinensisLOTUS Database
Pimpinella anisumLOTUS Database
Pinus mugo subsp. MugoLOTUS Database
Thymus marschallianusLOTUS Database
Vaccinium vitis-idaeaLOTUS Database
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
    • 

  • Bornane monoterpenoid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.83ALOGPS
logP1.99ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.31 m³·mol⁻¹ChemAxon
Polarizability18.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034976  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014588  
KNApSAcK IDC00011024  
Chemspider ID1013314  
KEGG Compound IDC01411  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1201518  
PDB IDNot Available
ChEBI ID15394  
Good Scents IDNot Available
References
General References
  1. Garcia GA, Soldi-Lose H, Nahon L, Powis I: Photoelectron circular dichroism spectroscopy in an orbitally congested system: the terpene endoborneol. J Phys Chem A. 2010 Jan 21;114(2):847-53. doi: 10.1021/jp909344r. [PubMed:20038111  ] 
  2. LOTUS database [Link]