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Showing NP-Card for 4-thujanol (NP0145348)

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Record Information
Version2.0
Created at2022-09-02 00:31:42 UTC
Updated at2022-09-02 00:31:42 UTC
NP-MRD IDNP0145348
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-thujanol
Description(1R,2R,5S)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]Hexan-2-ol belongs to the class of organic compounds known as bicyclic monoterpenoids. 4-thujanol is found in Achillea grandifolia, Citrus hystrix, Eucalyptus camaldulensis, Lantana ukambensis and Lavandula stoechas. These are monoterpenoids containing exactly 2 rings, which are fused to each other (1R,2R,5S)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]Hexan-2-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0145348 (4-thujanol)


  Mrv1652309272007292D          

 11 12  0  0  0  0            999 V2000
10002.8310 9996.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0501 9997.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3827 9997.0867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.6376 9996.3021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.4626 9996.3021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.7175 9997.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8304 9997.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0235 9997.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0849 9998.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5273 9995.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2248 9995.9864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  6  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
  3  1  1  6  0  0  0
  4  1  1  6  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  6  0  0  0
  5 11  1  1  0  0  0
M  END
Download

3D MOL for NP0145348 (4-thujanol)

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.2593   -1.4120    1.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.6179   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8349    0.5458   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829   -0.0370   -0.0539 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0176    0.2646    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248    0.7511    1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9265   -0.2298    0.0532 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9932    0.4918   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4314   -1.3855    0.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.5019   -0.7818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0124    0.7584   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8019   -2.4207    1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -0.8370    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3557   -1.5758    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900   -1.2365   -1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7588    0.2556   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    1.3688   -0.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159    0.9363    0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931    0.9734    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1058   -0.6730    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432    0.7247    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636    1.7968    0.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384   -0.1986   -1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5805    1.1268   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    1.1876   -1.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504   -1.0767    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6855   -1.3962   -1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4025    1.7433   -1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5932    0.6735   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  2  1  1
  4 11  1  0
 11 10  1  0
 10  7  1  0
  7  8  1  0
  7  9  1  1
  7  6  1  0
  6  5  1  0
 10  4  1  0
  5  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
 11 28  1  0
 11 29  1  0
 10 27  1  6
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  6 21  1  0
  6 22  1  0
  5 19  1  0
  5 20  1  0
M  END
Download

3D SDF for NP0145348 (4-thujanol)


  Mrv1652309272007292D          

 11 12  0  0  0  0            999 V2000
10002.8310 9996.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0501 9997.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3827 9997.0867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.6376 9996.3021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.4626 9996.3021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.7175 9997.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8304 9997.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0235 9997.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0849 9998.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5273 9995.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2248 9995.9864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  6  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
  3  1  1  6  0  0  0
  4  1  1  6  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  6  0  0  0
  5 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0145348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]12C[C@H]1[C@](C)(O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8-,9+,10-/m0/s1

> <INCHI_KEY>
KXSDPILWMGFJMM-AEJSXWLSSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.681223200435564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
1.8920337026666663

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.131154204711283

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9918331508592838

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
45.5544

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0145348 (4-thujanol)

Download
PDB for NP0145348 (4-thujanol)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8671.9518660.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8674.2278662.134   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8672.9818661.229   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8673.4578659.764   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8674.9978659.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8675.4738661.229   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.9508662.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.4448662.052   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8672.4258663.837   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8675.1188658.229   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8676.4208659.175   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    3    6                                                       
CONECT    3    2    4    1    7                                             
CONECT    4    3    5    1                                                  
CONECT    5    4    6   10   11                                             
CONECT    6    2    5                                                       
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0145348 (4-thujanol)
Download
SMILES for NP0145348 (4-thujanol)
CC(C)[C@]12C[C@H]1[C@](C)(O)CC2
Download
INCHI for NP0145348 (4-thujanol)
InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8-,9+,10-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
2-Methyl-5-(1-methylethyl)bicyclo(3.1.0)hexan-2-olMeSH
SabinenehydrateMeSH
trans-(-)-4-ThujanolPhytoBank
(1R,2R,5S)-2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-olPhytoBank
(E)-Sabinene hydratePhytoBank
2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-olPhytoBank
Sabinene hydratePhytoBank
4-ThujanolPhytoBank
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1R,2R,5S)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol
Traditional Name(1R,2R,5S)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol
CAS Registry NumberNot Available
SMILES
CC(C)[C@]12C[C@H]1[C@](C)(O)CC2
InChI Identifier
InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8-,9+,10-/m0/s1
InChI KeyKXSDPILWMGFJMM-AEJSXWLSSA-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
Achillea grandifoliaLOTUS Database
Citrus hystrixLOTUS Database
Eucalyptus camaldulensisLOTUS Database
Lantana ukambensisLOTUS Database
Lavandula stoechasLOTUS 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
    • 

  • Thujane monoterpenoid
    • 

  • Tertiary alcohol
    • 

  • Cyclic 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
logP2.12ALOGPS
logP1.89ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)19.13ChemAxon
pKa (Strongest Basic)-0.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.55 m³·mol⁻¹ChemAxon
Polarizability18.68 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6326181  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]