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Showing NP-Card for (+)-borneol (NP0271057)

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Record Information
Version2.0
Created at2022-09-08 17:13:00 UTC
Updated at2022-09-08 17:13:00 UTC
NP-MRD IDNP0271057
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-borneol
Description(+)-Isoborneol, also known as isobornyl alcohol, belongs to the class of organic compounds known as bicyclic monoterpenoids. (+)-borneol is found in Abies sibirica, Achillea millefolium, Ageratum conyzoides, Ajania fastigiata, Anthemis aciphylla, Artemisia annua, Artemisia halophila, Artemisia thuscula, Artemisia vulgaris, Brillantaisia lamium, Cistus clusii, Cistus incanus, Cleonia lusitanica, Clinopodium serpyllifolium, Croton sarcopetalus, Curcuma aeruginosa, Curcuma pierreana, Curcuma xanthorrhiza, Cymbopogon distans, Cymbopogon flexuosus, Cyperus rotundus, Gossypium hirsutum, Hamamelis virginiana, Helichrysum odoratissimum, Juniperus taxifolia, Larix sibirica, Lavandula angustifolia, Matricaria chamomilla, Micromeria biflora, Micromeria cristata, Monardella hypoleuca, Ocimum americanum, Origanum cordifolium, Origanum minutiflorum, Persicaria minor, Piper guineense, Plectranthus glabratus, Salvia absconditiflora, Salvia fruticosa, Salvia officinalis, Salvia syriaca, Santolina chamaecyparissus, Sideritis athoa, Thymus eigii, Thymus longicaulis, Thymus sipyleus, Thymus vulgaris, Thymus zygioides, Valeriana officinalis, Zingiber officinale and Zingiber zerumbet. These are monoterpenoids containing exactly 2 rings, which are fused to each other (+)-Isoborneol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0271057 ((+)-borneol)


  Mrv1652303062020462D          

 11 12  0  0  1  0            999 V2000
    2.1600   -1.5380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8742   -1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8742   -2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600   -3.1872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4458   -2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3366   -2.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -2.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444   -1.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -1.5146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -0.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  6  0  0  0
  1 11  1  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  8  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 10  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0271057 ((+)-borneol)

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    1.3023   -1.0386    1.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368   -0.0738    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8756    0.1387   -0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375    1.2824    0.7286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0712    1.9861   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022    0.8609   -1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312   -0.3985   -0.4415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6348   -1.6500   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3844   -0.2990    0.8058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3125   -1.4552    1.5851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526    0.8835    1.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1210   -2.0671    0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -0.9039    2.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4214   -0.9175    1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7508   -0.5409   -0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4831   -0.0189   -1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3074    1.1727   -0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2378    1.7697    1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7222    2.4288   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    2.7822   -0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931    1.0430   -1.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4255    0.7667   -2.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2780   -2.0948   -1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -2.4105   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3303   -1.5018   -2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4068   -0.0967    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -2.0251    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    1.7222    1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5385    0.6554    2.5924 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  6
  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  1
  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  6
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for NP0271057 ((+)-borneol)


  Mrv1652303062020462D          

 11 12  0  0  1  0            999 V2000
    2.1600   -1.5380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8742   -1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8742   -2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600   -3.1872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4458   -2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3366   -2.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -2.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444   -1.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -1.5146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -0.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  6  0  0  0
  1 11  1  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  8  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 10  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271057

> <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-OYNCUSHFSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.447352999747377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0271057 ((+)-borneol)

Download
PDB for NP0271057 ((+)-borneol)
HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0       4.032  -2.871   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.365  -3.642   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.365  -5.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.032  -5.949   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.699  -5.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.699  -3.642   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.228  -5.193   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.900  -4.408   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.243  -3.651   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.395  -2.827   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.047  -1.329   0.000  0.00  0.00           C+0
CONECT    1    8   11    2    6                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    8    5                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   10                                                  
CONECT    7    8                                                            
CONECT    8    1    4    7    9                                             
CONECT    9    8                                                            
CONECT   10    6                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0271057 ((+)-borneol)
Download
SMILES for NP0271057 ((+)-borneol)
CC1(C)[C@H]2CC[C@]1(C)[C@@H](O)C2
Download
INCHI for NP0271057 ((+)-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
Download
View in JSmol
Synonyms
ValueSource
(1S,2S,4S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-olHMDB
(S,S,S)-(+)-IsoborneolHMDB
2-exo-Bornyl alcoholHMDB
IsoborneolHMDB
Isobornyl alcoholHMDB
exo-2-Hydroxy-1,7,7-trimethylnorbornaneHMDB
(+)-IsoborneolHMDB
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional Name(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
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-OYNCUSHFSA-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 sibiricaLOTUS Database
Achillea millefoliumLOTUS Database
Ageratum conyzoidesLOTUS Database
Ajania fastigiataLOTUS Database
Anthemis aciphyllaLOTUS Database
Artemisia annuaLOTUS Database
Artemisia halophilaLOTUS Database
Artemisia thusculaLOTUS Database
Artemisia vulgarisLOTUS Database
Brillantaisia lamiumLOTUS Database
Cistus clusiiLOTUS Database
Cistus incanusLOTUS Database
Cleonia lusitanicaLOTUS Database
Clinopodium serpyllifoliumLOTUS Database
Croton sarcopetalusLOTUS Database
Curcuma aeruginosaLOTUS Database
Curcuma pierreanaLOTUS Database
Curcuma xanthorrhizaLOTUS Database
Cymbopogon distansLOTUS Database
Cymbopogon flexuosusLOTUS Database
Cyperus rotundusLOTUS Database
Gossypium hirsutumLOTUS Database
Hamamelis virginianaLOTUS Database
Helichrysum odoratissimumLOTUS Database
Juniperus taxifoliaLOTUS Database
Larix sibiricaLOTUS Database
Lavandula angustifoliaLOTUS Database
Matricaria chamomillaLOTUS Database
Micromeria bifloraLOTUS Database
Micromeria cristataLOTUS Database
Monardella hypoleucaLOTUS Database
Ocimum americanumLOTUS Database
Origanum cordifoliumLOTUS Database
Origanum minutiflorumLOTUS Database
Persicaria minorLOTUS Database
Piper guineenseLOTUS Database
Plectranthus glabratusLOTUS Database
Salvia absconditifloraLOTUS Database
Salvia fruticosaLOTUS Database
Salvia officinalisLOTUS Database
Salvia syriacaLOTUS Database
Santolina chamaecyparissusLOTUS Database
Sideritis athoaLOTUS Database
Thymus eigiiLOTUS Database
Thymus longicaulisLOTUS Database
Thymus sipyleusLOTUS Database
Thymus vulgarisLOTUS Database
Thymus zygioidesLOTUS Database
Valeriana officinalisLOTUS Database
Zingiber officinaleLOTUS Database
Zingiber zerumbetLOTUS 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 DescriptorsNot Available
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
Polarizability18.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035815  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014576  
KNApSAcK IDNot Available
Chemspider ID16739225  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6973640  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]