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Showing metabocard for alpha-Terpineol (HMDB0004043)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 09:35:11 UTC
Update Date2023-02-21 17:16:51 UTC
HMDB IDHMDB0004043
Secondary Accession Numbers
  • HMDB0036086
  • HMDB04043
  • HMDB36086
Metabolite 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
Data?1676999811
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004043 (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 HMDB0004043 (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 HMDB0004043 (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>
HMDB0004043

> <DATABASE_NAME>
hmdb

> <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 HMDB0004043 (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 HMDB0004043 (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 HMDB0004043 (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 HMDB0004043 (alpha-Terpineol)

CC1=CC[C@@H](CC1)C(C)(C)O
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INCHI for HMDB0004043 (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 JSmolView Stereo Labels
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, MeSH
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-TerpineolMeSH, HMDB
alpha-Terpineol, sodium saltMeSH, HMDB
P-Menth-1-en-8-olMeSH, HMDB
D-alpha-TerpineolMeSH, HMDB
(S)-a-TerpineolGenerator, HMDB
(S)-Α-terpineolGenerator, HMDB
alpha-TerpineolMeSH
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol
Traditional Name(+)-α-terpineol
CAS Registry Number7785-53-7
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
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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular 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,EM (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.7531661259
DarkChem[M-H]-134.77531661259
DeepCCS[M+H]+142.29930932474
DeepCCS[M-H]-139.90330932474
DeepCCS[M-2H]-174.14530932474
DeepCCS[M+Na]+148.42930932474
AllCCS[M+H]+133.432859911
AllCCS[M+H-H2O]+129.032859911
AllCCS[M+NH4]+137.532859911
AllCCS[M+Na]+138.732859911
AllCCS[M-H]-138.932859911
AllCCS[M+Na-2H]-140.632859911
AllCCS[M+HCOO]-142.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.4.79 minutes32390414
Predicted by Siyang on May 30, 202214.041 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.73 minutes32390414

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-Terpineol[H][C@]1(CCC(C)=CC1)C(C)(C)O1688.3Standard polar33892256
alpha-Terpineol[H][C@]1(CCC(C)=CC1)C(C)(C)O1174.4Standard non polar33892256
alpha-Terpineol[H][C@]1(CCC(C)=CC1)C(C)(C)O1184.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Terpineol,1TMS,isomer #1CC1=CC[C@H](C(C)(C)O[Si](C)(C)C)CC11314.6Semi standard non polar33892256
alpha-Terpineol,1TBDMS,isomer #1CC1=CC[C@H](C(C)(C)O[Si](C)(C)C(C)(C)C)CC11558.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - alpha-Terpineol GC-EI-Q (Non-derivatized)splash10-052f-9200000000-ae93728615d3c506a1ce2020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Terpineol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-a6b151ba8e67f64241ac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Terpineol GC-MS (1 TMS) - 70eV, Positivesplash10-01qi-9620000000-6c96b32bd4033639edd22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Terpineol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Terpineol Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0540-5900000000-cda96dbf2d059d85a3c52012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Terpineol Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-001i-9000000000-ef81a719227e0ca1dabc2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Terpineol Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-057l-9000000000-f219b3601875dbade6b92012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 10V, Positive-QTOFsplash10-052r-1900000000-3e8ebaa4ae0750710d122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 20V, Positive-QTOFsplash10-052k-9600000000-de13f72872a89c9b2a522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 40V, Positive-QTOFsplash10-0le9-9100000000-f6bc053d285b0f1e22f42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 10V, Negative-QTOFsplash10-0udi-0900000000-0b1926cd4fc400a61e842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 20V, Negative-QTOFsplash10-0udj-3900000000-b512881ea0d1ea0511992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 40V, Negative-QTOFsplash10-000b-9400000000-90c166242df69d6dee012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 10V, Negative-QTOFsplash10-0udi-0900000000-118ad26f2b30eb1cab8b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 20V, Negative-QTOFsplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 40V, Negative-QTOFsplash10-0f6x-9500000000-4ef1ecf90c5038ba6f9e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 10V, Positive-QTOFsplash10-000i-5900000000-4a5f3c6978eb2913079e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 20V, Positive-QTOFsplash10-05mn-9100000000-e7d43b2d0a8d389277d12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpineol 40V, Positive-QTOFsplash10-00kf-9000000000-c647649541c827cabb3b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1508221
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Mondello F, De Bernardis F, Girolamo A, Cassone A, Salvatore G: In vivo activity of terpinen-4-ol, the main bioactive component of Melaleuca alternifolia Cheel (tea tree) oil against azole-susceptible and -resistant human pathogenic Candida species. BMC Infect Dis. 2006 Nov 3;6:158. [PubMed:17083732 ]
  3. 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 ]
  4. Calcabrini A, Stringaro A, Toccacieli L, Meschini S, Marra M, Colone M, Salvatore G, Mondello F, Arancia G, Molinari A: Terpinen-4-ol, the main component of Melaleuca alternifolia (tea tree) oil inhibits the in vitro growth of human melanoma cells. J Invest Dermatol. 2004 Feb;122(2):349-60. [PubMed:15009716 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.