Np mrd loader

Showing NP-Card for Alpha-Terpineol (NP0000822)

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Record Information
Version2.0
Created at2006-08-13 09:35:11 UTC
Updated at2021-10-07 20:41:31 UTC
NP-MRD IDNP0000822
Secondary Accession Numbers
  • NP0001085
Natural Product Identification
Common NameAlpha-Terpineol
DescriptionAlpha-Terpineol (CAS: 98-55-5) Is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers of terpineol, alpha-, beta-, and gamma-terpineol, with the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. Terpineol has a pleasant odour similar to lilac and is a common ingredient in perfumes, cosmetics, and flavours. Alpha-Terpineol is occasionally found as a volatile component in urine. It is a water-soluble component of Melaleuca alternifolia Cheel, the tea tree oil (TTO). Alpha-Terpineol is a likely mediator of the in vitro and in vivo activity of the TTO as an agent that could control C. Albicans vaginal infections. Purified alpha-terpineol can suppress pro-inflammatory mediator production by activated human monocytes. Alpha-Terpineol is able to impair the growth of human M14 melanoma cells and appear to be more effective on their resistant variants, which express high levels of P-glycoprotein in the plasma membrane, overcoming resistance to caspase-dependent apoptosis exerted by P-glycoprotein-positive tumour cells (PMID: 5556886 , 17083732 , 11131302 , 15009716 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000822 (Alpha-Terpineol)


  Mrv1652309042019472D          

 11 11  0  0  0  0            999 V2000
   -1.0491    2.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0491    0.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    1.6848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4780    0.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3798    2.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0943    1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7923    2.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    2.8117    0.0000 O   0  0  0  0  0  0  0  0  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000822 (Alpha-Terpineol)

HMDB0004043
     RDKit          3D
alpha-Terpineol
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.8707    0.1009    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    0.0286    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791   -1.0991    0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232   -1.3221   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762   -0.1256    0.3300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8387   -0.1097   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937    1.1159    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5849   -1.3646   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -0.0346   -1.7055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2590    1.1126   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5714    1.2384    0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194    1.0743    0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2264   -0.0345    1.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705   -0.7073   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236   -1.9527   -0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0316   -2.2095    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0238   -1.5789   -1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162   -0.0380    1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5450    1.2639    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739    0.9494   -0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861    2.0225   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6517   -1.2323   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009   -1.6580    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1223   -2.1888   -0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4615    0.2368   -2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2993    2.0348    0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    0.9791   -1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694    2.1440    0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3354    1.3544    1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  1
  7 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for NP0000822 (Alpha-Terpineol)


  Mrv1652309042019472D          

 11 11  0  0  0  0            999 V2000
   -1.0491    2.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0491    0.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    1.6848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4780    0.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3798    2.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0943    1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7923    2.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    2.8117    0.0000 O   0  0  0  0  0  0  0  0  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@@H](CC1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1

> <INCHI_KEY>
WUOACPNHFRMFPN-VIFPVBQESA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.068760635093753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.1742975076666666

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.402266970394027

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8732484271496527

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.4619

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-α-terpineol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000822 (Alpha-Terpineol)

HMDB0004043
     RDKit          3D
alpha-Terpineol
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.8707    0.1009    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    0.0286    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791   -1.0991    0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232   -1.3221   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762   -0.1256    0.3300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8387   -0.1097   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937    1.1159    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5849   -1.3646   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -0.0346   -1.7055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2590    1.1126   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5714    1.2384    0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194    1.0743    0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2264   -0.0345    1.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705   -0.7073   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236   -1.9527   -0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0316   -2.2095    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0238   -1.5789   -1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162   -0.0380    1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5450    1.2639    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739    0.9494   -0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861    2.0225   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6517   -1.2323   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009   -1.6580    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1223   -2.1888   -0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4615    0.2368   -2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2993    2.0348    0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    0.9791   -1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694    2.1440    0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3354    1.3544    1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  1
  7 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

PDB for NP0000822 (Alpha-Terpineol)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.958   3.915   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.292   3.145   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.292   1.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.958   0.835   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.625   1.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.625   3.145   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.626   0.835   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.709   3.915   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.043   3.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.479   5.249   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.061   5.249   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    3                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000822 (Alpha-Terpineol)

COMPND    HMDB0004043
HETATM    1  C1  UNL     1       3.871   0.101   0.372  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.366   0.029   0.325  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.779  -1.099   0.009  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.323  -1.322  -0.078  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.476  -0.126   0.330  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.839  -0.110  -0.332  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.594   1.116   0.118  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.585  -1.365  -0.007  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.620  -0.035  -1.705  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.259   1.113  -0.129  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.571   1.238   0.639  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.219   1.074   0.017  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.226  -0.034   1.412  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.270  -0.707  -0.282  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.424  -1.953  -0.211  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.032  -2.209   0.535  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.024  -1.579  -1.131  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.616  -0.038   1.425  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.545   1.264   1.218  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.674   0.949  -0.167  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.286   2.023  -0.428  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.652  -1.232  -0.288  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.501  -1.658   1.059  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.122  -2.189  -0.616  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.461   0.237  -2.156  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.299   2.035   0.044  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.501   0.979  -1.203  1.00  0.00           H  
HETATM   28  H17 UNL     1       2.069   2.144   0.252  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.335   1.354   1.697  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6   10   18
CONECT    6    7    8    9
CONECT    7   19   20   21
CONECT    8   22   23   24
CONECT    9   25
CONECT   10   11   26   27
CONECT   11   28   29
END
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SMILES for NP0000822 (Alpha-Terpineol)

CC1=CC[C@@H](CC1)C(C)(C)O
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INCHI for NP0000822 (Alpha-Terpineol)

InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1
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View in JSmol
Synonyms
ValueSource
(+)-p-Menth-1-en-8-olChEBI
(1R)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolChEBI
(R)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanolChEBI
(R)-alpha-TerpineolChEBI
(+)-alpha-TerpineolKegg
(1R)-a,a,4-Trimethyl-3-cyclohexene-1-methanolGenerator
(1R)-Α,α,4-trimethyl-3-cyclohexene-1-methanolGenerator
(R)-a,a,4-Trimethylcyclohex-3-ene-1-methanolGenerator
(R)-Α,α,4-trimethylcyclohex-3-ene-1-methanolGenerator
(R)-a-TerpineolGenerator
(R)-Α-terpineolGenerator
(+)-a-TerpineolGenerator
(+)-Α-terpineolGenerator
a-TerpineolGenerator
Α-terpineolGenerator
(6R)-p-Menth-1-en-8-olHMDB
(R)-(+)-alpha-TerpineolHMDB
(R)-2-(4-Methyl-3-cyclohexenyl)isopropanolHMDB
(R)-p-Menth-1-en-8-olHMDB
(S)-(-)-p-Menth-1-en-8-olHMDB
1-alpha-TerpineolHMDB
2-(4-Methyl-3-cyclohexen-1-yl)-2-propanolHMDB
2-(4-Methylcyclohex-3-en-1-yl)propan-2-olHMDB
2-(4-Methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol)HMDB
2-[(1R)-4-Methylcyclohex-3-en-1-yl]propan-2-olHMDB
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanolHMDB
alpha-TerpinenolHMDB
alpha-TerpineoleHMDB
alpha-TerpinolHMDB
L-alpha-TerpineolHMDB
Lily OF valleyHMDB
TerpenolHMDB
TerpineolHMDB
Terpineol schlechthinHMDB
DL-alpha-TerpineolHMDB
alpha-Terpineol, sodium saltHMDB
p-Menth-1-en-8-olHMDB
D-alpha-TerpineolHMDB
(S)-a-TerpineolHMDB
(S)-Α-terpineolHMDB
alpha-TerpineolMeSH
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol
Traditional Name(+)-α-terpineol
CAS Registry Number98-55-5
SMILES
CC1=CC[C@@H](CC1)C(C)(C)O
InChI Identifier
InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1
InChI KeyWUOACPNHFRMFPN-VIFPVBQESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies albaLOTUS Database
Abies sachalinensisLOTUS Database
Achillea millefoliumLOTUS Database
Acokanthera oblongifoliaLOTUS Database
Acorus calanus L.Plant
Ageratina conyzoidesPlant
Aloysia citrodoraLOTUS Database
Alphinia galanga-
Ambrosia trifidaPlant
Amomum krervanhPlant
Ananas comosusFooDB
Anethum graveolensFooDB
Anthemis aciphylla BOISS.var.discoidea BOISSPlant
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Apium graveolens var. rapaceumFooDB
    • Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Arachis hypogaeaPlant
Aristolochia trilobataPlant
Artemisia anethoidesPlant
Artemisia annuaPlant
Artemisia argyiPlant
Artemisia capillarisPlant
Artemisia herba-albaLOTUS Database
Artemisia scopariaLOTUS Database
Artemisia spp.KNApSAcK Database
Artemisia vulgarisFooDB
Asarum canadenseLOTUS Database
Asarum heterotropoides var.mandshuricumPlant
Asarum sieboldiiPlant
Atalantia guillauminiiPlant
Azadirachta indicaPlant
Backhousia angustifoliaLOTUS Database
Baeckea frutescens-
Boeckea frutescens-
Brassica oleracea var. botrytisFooDB
    • L. Valettea X. Fernandez, S. Poulain, A.-M. Loiseau, L. Lizzani-Cuvelier, R. Levieil, L. Restier....
Brassica oleracea var. capitataFooDB
Bupleurum chinensePlant
Calamintha nepetaPlant
Camellia sinensisPlant
Cananga odorataPlant
Canarium zeylanicumLOTUS Database
Cannabis inflorescencesPlant
Cannabis sativaCannabisDB
      Not Available
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Carum carviFooDB
Catha edulisLOTUS Database
Cedrus libaniPlant
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum camphoraPlant
Cinnamomum illicioidesPlant
Cinnamomum spp.KNApSAcK Database
Cinnamomum verumFooDB
Cistus creticusPlant
Citrus aurantiifoliaFooDB
Citrus aurantiumPlant
Citrus junosLOTUS Database
Citrus latifoliaPlant
Citrus limonFooDB
Citrus paradisiPlant
Citrus reticulataFooDB
Citrus reticulate x Citrus sinensisPlant
Citrus sinensis L.Plant
Citrus unshiuLOTUS Database
Citrus wilsoniiLOTUS Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.Plant
Commiphora mukulPlant
Conyza newiiPlant
Coriandrum sativum L.FooDB
Cuminum cyminumFooDB
Curcuma aeruginosaPlant
Curcuma amanda RoxbPlant
Curcuma aromaticaPlant
Curcuma kwangsiensisPlant
Curcuma longaFooDB
Curcuma manggaPlant
Curcuma phaeocaulisPlant
Curcuma wenyujinPlant
Curcuma xanthorrhizaPlant
Cyathocline purpureaPlant
Cymbopogon citratusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • David M. Alabran, Howard R. Moskowitz, and Ahmed F. Mabrouk. Carrot-Root Oil Components and Their...
Dittrichia graveolensPlant
Elettaria cardamomumFooDB
Ephedra sinicaPlant
Espeletia timotensisLOTUS Database
Eucalyptus cinereaPlant
Eucalyptus globulus var. bicostataPlant
Eucalyptus mitchellianaLOTUS Database
Eucalyptus radiataPlant
Eucalyptus spp.KNApSAcK Database
Feijoa sellowianaPlant
Ficus caricaFooDB
Foeniculum vulgareFooDB
Forsythia suspensaPlant
Fragaria moschataLOTUS Database
Ganoderma lucidumFungi
Gentiana luteaPlant
Glechomia longituba-
Guarea macrophylla ssp.tuberculataPlant
Guatteria hispidaPlant
Helianthus annuus L.FooDB
Hesperis matronalisPlant
Hibiscus sabbariffaFooDB
Houttuynia cordataPlant
Houttuynia emeiensisPlant
Hyssopus officinalis L.FooDB
Ichthyothere terminalisLOTUS Database
Illicium verumFooDB
Jasminum grandiflorumPlant
Juniperus communisLOTUS Database
Juniperus drupaceaLOTUS Database
Juniperus scopulorumLOTUS Database
Juniperus spp.KNApSAcK Database
Lantana camaraLOTUS Database
Larix gmeliniLOTUS Database
Laurus nobilis L.FooDB
Lavandin abrialis-
Lavandula angustifoliaPlant
Lavandula canarien-sisPlant
Lavandula dentataPlant
Lavandula gibsoniPlant
Lavandula stoechasPlant
Leptospermum scopariumPlant
Levisticum officinaleFooDB
Ligusticum jeholensePlant
Lindera sericeaLOTUS Database
Lippia javanicaPlant
Lippia ukambensisPlant
Lonicera japonicaPlant
Lychnophora ericoidesPlant
Magnolia officinalisPlant
Melaleuca alternifoliaLOTUS Database
Melaleuca leucadendra L.Plant
Melissa officinalis L.FooDB
MenthaFooDB
Mentha arvensisPlant
Mentha pulegiumPlant
Mentha spicataFooDB
Mentha spp.KNApSAcK Database
Mentha x piperitaFooDB
Monarda fistulosaLOTUS Database
Monodora myristicaPlant
Murraya paniculataPlant
Myristica fragransFooDB
Myrtus communisPlant
Nicotiana alataPlant
Nicotiana langsdorffiiPlant
Nicotiana mutabilisPlant
Notopterygium forbesiiPlant
Ocimum basilicumFooDB
Oenanthe aquaticaLOTUS Database
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Perovskia angustifoliaPlant
Petroselinum crispumFooDB
Phagnalon sordidumPlant
Picea abiesLOTUS Database
Picea koraiensisLOTUS Database
Picea rubensLOTUS Database
Picea sitchensisLOTUS Database
Pimenta dioicaFooDB
Pimpinella anisumFooDB
Pinus halepensisPlant
Pinus mugo subsp. MugoPlant
Pinus sibiricaPlant
Pinus sylvestrisLOTUS Database
Pinus taedaPlant
Piper arboreumPlant
Piper fimbriulatumPlant
Piper nigrum L.FooDB
Plectranthus marrubioidesPlant
Prunus armeniacaFooDB
Prunus armeniaca var.ansuPlant
Prunus aviumPlant
Prunus persicaFooDB
Prunus salcina Lindl. (Friar)Plant
Psidium guajavaFooDB
Pyrus pyrifoliaFooDB
    • Gary R. Takeoka, Ron G. Buttery, and Robert A. Flath. Volatile Constituents of Asian Pear (Pyrus ...
Quercus agrifoliaLOTUS Database
Rhodiola roseaPlant
Rhynchosia minimaPlant
Ribes nigrumFooDB
Salix babylonicaPlant
Salvia lavendulifoliaPlant
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Santiria trimeraLOTUS Database
Santolina corsica Jordan et FourrPlant
Satureja hortensis L.FooDB
Satureja montanaFooDB
Saxifraga stolonifera Meerb.Plant
Schisandra chinensisPlant
Senecio vulgarisPlant
Sideritis chamaedrifoliaLOTUS Database
Spongiporus leucomallellus (Murril)-
Syzygium aromaticumFooDB
Syzygium formosanumPlant
Tabernaemontana catharinensisPlant
Tamarindus indicaFooDB
Tanacetum macrophyllumPlant
Tarchonanthus camphoratusPlant
Taxus baccataPlant
Tetradenia ripariaPlant
Thryptomene saxicolaLOTUS Database
Thymus marschallianusLOTUS Database
Thymus piperellaPlant
Thymus serpyllumPlant
Thymus vulgarisFooDB
Tilia L.FooDB
Tipuana tipuPlant
Trachyspermum roxburghianum-
Trichostema lanceolatumPlant
Trifolium repensPlant
Turnera diffusaPlant
Vaccinium corymbosumFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Valeriana jatamansiPlant
Valeriana officinalis var.latifoliaPlant
Viburnum dilatatumLOTUS Database
Vitex agnus-castusLOTUS Database
Vitex trifoliaPlant
VitisFooDB
Vitis vinifera L.FooDB
Xylopia aethiopicaPlant
Xylopia parvifloraPlant
Xylopia sericeaPlant
Zanthoxylum armatumPlant
Zanthoxylum bungeanumPlant
Zanthoxylum decaryiPlant
Zea mays L.FooDB
Zingiber officinaleFooDB
Zingiber zerumbetLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point37.5 °CNot Available
Boiling Point217.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.71 mg/mL at 25 °CNot Available
LogP2.98Li, J., Perdue, E.M. (1995) Physicochemical properties of selected monoterpenes. Pre-print Extended Abstract, Presented Before The Division of Environmental Chemistry, Amer Chem Soc, Anaheim, Ca: April 2-7
Predicted Properties
PropertyValueSource
Water Solubility1.56 g/LALOGPS
logP3.17ALOGPS
logP2.17ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)19.4ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.46 m³·mol⁻¹ChemAxon
Polarizability19.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004043
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014552
KNApSAcK IDC00029674
Chemspider ID390927
KEGG Compound IDC09902
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTerpineol
METLIN IDNot Available
PubChem Compound442501
PDB IDNot Available
ChEBI ID300
Good Scents IDrw1508221
References
General References
  1. Hart PH, Brand C, Carson CF, Riley TV, Prager RH, Finlay-Jones JJ: Terpinen-4-ol, the main component of the essential oil of Melaleuca alternifolia (tea tree oil), suppresses inflammatory mediator production by activated human monocytes. Inflamm Res. 2000 Nov;49(11):619-26. [PubMed:11131302 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  3. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.