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Showing NP-Card for alpha-Terpinene-4-ol (NP0044994)

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Record Information
Version2.0
Created at2022-03-10 18:52:25 UTC
Updated at2022-03-10 22:18:11 UTC
NP-MRD IDNP0044994
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Terpinene-4-ol
DescriptionAlpha-Terpinene-4-ol, also known as terpinen-4-ol, 1-para-menthen-4-ol or p-Menth-1-en-4-ol or 4-carvomenthenol, is an isomer of terpineol. It 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. Alpha-Terpinene-4-ol is a hydrophobic, largely neutral molecule that is essentially insoluble in water.  It has a peppery, spicy, musty, citrus odor and a cooling woody or spicy taste.  Alpha-Terpinene-4-ol is widely used as a flavoring agent and as a masking agent in cosmetics.  Alpha-Terpinene-4-ol is a natural product that can be found in a number of plants, such as allspice, anise, apple, basil, cardamom, cinnamon and Melaleuca alternifolia (also called tea tree) and is the main bioactive component of tea tree oil (PMID 22083482 ).  Alpha-Terpinene-4-ol is also one of the monoterpenes found in cannabis plants (PMID: 6991645 ).   Terpinen-4-ol is a potent bactericidal agent that also possess antifungal properties. In particular, it has shown in vitro activity against Staphylococcus aureus and C. Albicans (PMID: 27275783 ). It has also been shown that combining this natural substance and conventional drugs may help treat resistant yeast and bacterial infections.  Several studies have suggested that terpinen-4-ol induces antitumor effects by selectively causing necrotic cell death and cell-cycle arrest in melanoma cell lines, or by triggering caspase-dependent apoptosis in human melanoma cells (PMID: 27275783 ).  
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044994 (alpha-Terpinene-4-ol)

Carvomenthanol (4-)
  Mrv1652303202019022D          

 11 11  0  0  1  0            999 V2000
    2.1615    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    0.5231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9866    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
M  END
Download

3D MOL for NP0044994 (alpha-Terpinene-4-ol)

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.3577    0.9607    0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489    0.2553   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3078    0.7866   -0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -0.0383   -1.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463   -0.7240   -0.1908 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8596   -2.0569   -0.5712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741   -0.1155    0.2041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8434   -0.1422   -0.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    1.3245    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779   -0.8742    0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7814   -1.0856    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995    0.2820    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588    1.6446   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    1.5552    1.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4776    1.7816   -1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4976   -0.8102   -2.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.6032   -1.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5675   -2.3788    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979   -0.7115    1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -1.0647   -1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6200    0.7406   -1.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8606   -0.0287   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0142    2.0053   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707    1.4960    1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8033    1.5792    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1451   -1.7641    1.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048    0.0286    1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179   -1.7878   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853   -1.4608    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  7  5  1  0
  5  6  1  6
  5 10  1  0
 10 11  1  0
 11  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  7 19  1  1
  9 23  1  0
  9 24  1  0
  9 25  1  0
  6 18  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  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
M  END
Download

3D SDF for NP0044994 (alpha-Terpinene-4-ol)

Carvomenthanol (4-)
  Mrv1652303202019022D          

 11 11  0  0  1  0            999 V2000
    2.1615    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    0.5231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9866    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044994

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]1(O)CCC(C)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1

> <INCHI_KEY>
WRYLYDPHFGVWKC-SNVBAGLBSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.704458168600958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.3302049676666665

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.999288199495165

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6121113415408138

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.3079

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-isopropyl-4-methylcyclohex-3-en-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0044994 (alpha-Terpinene-4-ol)

Download
PDB for NP0044994 (alpha-Terpinene-4-ol)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Carvomenthanol (4-)                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0       4.035   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.805   0.976   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.575   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.139   0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.471   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.139  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.805  -2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.471  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.115   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.805   3.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.805  -3.644   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2    9   10                                                  
CONECT    4    2    6                                                       
CONECT    5    2    8                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    5    7                                                       
CONECT    9    3                                                            
CONECT   10    3                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0044994 (alpha-Terpinene-4-ol)
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SMILES for NP0044994 (alpha-Terpinene-4-ol)
CC(C)[C@]1(O)CCC(C)=CC1
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INCHI for NP0044994 (alpha-Terpinene-4-ol)
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(+)-Terpinen-4-olHMDB
(S)-(+)-p-Menth-1-en-4-olHMDB
(S)-1-Isopropyl-4-methyl-3-cyclohexen-1-olHMDB
S-4-CarvomenthenolHMDB
S-OriganolHMDB
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
Traditional Name(1S)-1-isopropyl-4-methylcyclohex-3-en-1-ol
CAS Registry Number2438-10-0
SMILES
CC(C)[C@]1(O)CCC(C)=CC1
InChI Identifier
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1
InChI KeyWRYLYDPHFGVWKC-SNVBAGLBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies sachalinensisLOTUS Database
Acorus calamusLOTUS Database
Acorus gramineusLOTUS Database
Anthemis aciphyllaLOTUS Database
Artemisia annuaLOTUS Database
Artemisia herba-albaLOTUS Database
Artemisia scopariaLOTUS Database
Artemisia vulgarisLOTUS Database
Cannabis sativaNULL
      Not Available
Cedrus libaniLOTUS Database
Chamaecyparis formosensisLOTUS Database
Chamaecyparis obtusaLOTUS Database
Cistus creticusLOTUS Database
Citrus junosLOTUS Database
Citrus sinensisLOTUS Database
Citrus wilsoniiLOTUS Database
Cryptomeria japonicaLOTUS Database
Cyperus rotundusLOTUS Database
Espeletia timotensisLOTUS Database
Eucalyptus crenulataLOTUS Database
Houttuynia cordataLOTUS Database
Juniperus communisLOTUS Database
Larix gmeliniLOTUS Database
Laurus nobilisLOTUS Database
Libocedrus bidwilliiLOTUS Database
Liquidambar formosanaLOTUS Database
Melaleuca alternifoliaLOTUS Database
Mentha pulegiumLOTUS Database
Mosla chinensisLOTUS Database
Oenanthe aquaticaLOTUS Database
Picea rubensLOTUS Database
Pimpinella anisumLOTUS Database
Pinus densifloraLOTUS Database
Pinus pumilaLOTUS Database
Pinus sylvestrisLOTUS Database
Piper aduncumLOTUS Database
Piper arboreumLOTUS Database
Sideritis leucanthaLOTUS Database
Tanacetum longifoliumLOTUS Database
Tanacetum vulgareLOTUS Database
Thujopsis dolabrataLOTUS Database
Vitex agnus-castusLOTUS 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 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
logP2.81ALOGPS
logP2.33ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)20ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.31 m³·mol⁻¹ChemAxon
Polarizability18.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035823  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014586  
KNApSAcK IDC00010928  
Chemspider ID2006320  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2724161  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References