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Showing NP-Card for 1-p-menthene-8-thiol (NP0252221)

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Record Information
Version2.0
Created at2022-09-07 15:39:41 UTC
Updated at2022-09-07 15:39:41 UTC
NP-MRD IDNP0252221
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-p-menthene-8-thiol
DescriptionP-Menth-1-ene-8-thiol, also known as 8-mercapto-p-menth-1-ene or fema 3700, 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. P-Menth-1-ene-8-thiol is an extremely weak basic (essentially neutral) compound (based on its pKa). P-Menth-1-ene-8-thiol is an aromatic, grapefruit, and naphthyl tasting compound. Outside of the human body, p-Menth-1-ene-8-thiol has been detected, but not quantified in, citrus. 1-p-menthene-8-thiol is found in Citrus paradisi. This could make p-menth-1-ene-8-thiol a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0252221 (1-p-menthene-8-thiol)


  Mrv0541 05061308392D          

 11 11  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
Download

3D MOL for NP0252221 (1-p-menthene-8-thiol)

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.7622   -0.3686   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -0.0738   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7598   -0.2572    1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.0351    1.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4251   -0.5290    0.0727 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8844   -0.2619    0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2354    1.1900    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455   -0.8655   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3712   -1.0572    1.8432 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -0.0578   -1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5253    0.4017   -1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3871    0.2343    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9871   -1.4401   -0.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1028   -0.0930   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3886   -0.6131    1.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0286   -0.5033    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060    1.1132    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858   -1.6312    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6920    1.8398   -0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309    1.5905    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148    1.2933    0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622   -1.9069   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831   -0.8631   -0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6717   -0.2457   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9071   -0.2593    2.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5273    0.7725   -1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0119   -0.8671   -2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486    0.0874   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608    1.5286   -1.2324 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 10  1  0
 10 11  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  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  6
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
  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
M  END
Download

3D SDF for NP0252221 (1-p-menthene-8-thiol)


  Mrv0541 05061308392D          

 11 11  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC(CC1)C(C)(C)S

> <INCHI_IDENTIFIER>
InChI=1S/C10H18S/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3

> <INCHI_KEY>
ZQPCOAKGRYBBMR-UHFFFAOYSA-N

> <FORMULA>
C10H18S

> <MOLECULAR_WEIGHT>
170.315

> <EXACT_MASS>
170.112921266

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
20.89029238348657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)propane-2-thiol

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
3.218110975

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.959337032181024

> <JCHEM_PKA_STRONGEST_BASIC>
-9.7812112672069

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
54.588899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
grapefruit mercaptan

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0252221 (1-p-menthene-8-thiol)

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PDB for NP0252221 (1-p-menthene-8-thiol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0       2.874   3.850   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    6    8                                                       
CONECT    5    7    8                                                       
CONECT    6    4    9                                                       
CONECT    7    5    9                                                       
CONECT    8    1    4    5                                                  
CONECT    9    6    7   10                                                  
CONECT   10    2    3    9   11                                             
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0252221 (1-p-menthene-8-thiol)
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SMILES for NP0252221 (1-p-menthene-8-thiol)
CC1=CCC(CC1)C(C)(C)S
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INCHI for NP0252221 (1-p-menthene-8-thiol)
InChI=1S/C10H18S/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
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View in JSmol
Synonyms
ValueSource
1-p-Menthen-8-thiolHMDB
1-p-Menthene-8-thiolHMDB
4-(1-Mercapto-1-methylethyl)-1-methylcyclohexeneHMDB
8-Mercapto-p-menth-1-eneHMDB
a,a,4-Trimethyl-3-cyclohexene-1-methanethiol, 9ciHMDB
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanethiolHMDB
alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanethiolHMDB
FEMA 3700HMDB
p-1-Menthen-8-thiolHMDB
p-1-Menthene-8-thiolHMDB
p-Menth-1-en-8-thiolHMDB
Chemical FormulaC10H18S
Average Mass170.3150 Da
Monoisotopic Mass170.11292 Da
IUPAC Name2-(4-methylcyclohex-3-en-1-yl)propane-2-thiol
Traditional Namegrapefruit mercaptan
CAS Registry NumberNot Available
SMILES
CC1=CCC(CC1)C(C)(C)S
InChI Identifier
InChI=1S/C10H18S/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
InChI KeyZQPCOAKGRYBBMR-UHFFFAOYSA-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
Citrus paradisiLOTUS 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
    • 

  • Alkylthiol
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • 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
logP4.46ALOGPS
logP3.22ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity54.59 m³·mol⁻¹ChemAxon
Polarizability20.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035703  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014423  
KNApSAcK IDNot Available
Chemspider ID4932553  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6427135  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]