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Showing NP-Card for 8-Mercapto-p-menthan-3-one (NP0337386)

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Record Information
Version2.0
Created at2024-09-11 10:36:38 UTC
Updated at2024-09-11 10:36:38 UTC
NP-MRD IDNP0337386
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-Mercapto-p-menthan-3-one
Description8-Mercapto-p-menthan-3-one 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. 8-Mercapto-p-menthan-3-one was first documented in 2019 (PMID: 32626076). Based on a literature review very few articles have been published on 8-Mercapto-p-menthan-3-one (PMID: 36626784).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337386 (8-Mercapto-p-menthan-3-one)


  Mrv2104 05262313082D          

 12 12  0  0  0  0            999 V2000
   -3.0469   -2.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -3.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -3.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0469   -4.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -3.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -3.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0469   -1.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179   -4.2938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0469   -5.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -5.5313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614   -5.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0469   -5.9438    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  5  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
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3D MOL for NP0337386 (8-Mercapto-p-menthan-3-one)

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3D SDF for NP0337386 (8-Mercapto-p-menthan-3-one)

  Mrv2104 05262313082D          

 12 12  0  0  0  0            999 V2000
   -3.0469   -2.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -3.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -3.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0469   -4.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -3.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -3.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0469   -1.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179   -4.2938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0469   -5.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324   -5.5313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614   -5.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0469   -5.9438    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  5  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337386

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(C(=O)C1)C(C)(C)S

> <INCHI_IDENTIFIER>
InChI=1/C10H18OS/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-8,12H,4-6H2,1-3H3

> <INCHI_KEY>
RVOKNSFEAOYULQ-UHFFFAOYNA-N

> <FORMULA>
C10H18OS

> <MOLECULAR_WEIGHT>
186.31

> <EXACT_MASS>
186.107836374

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.67051483091526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-2-(2-sulfanylpropan-2-yl)cyclohexan-1-one

> <JCHEM_LOGP>
2.7783936429999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.896284933109355

> <JCHEM_PKA_STRONGEST_BASIC>
-7.441100563530373

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
54.3292

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
p-mentha-8-thiol-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0337386 (8-Mercapto-p-menthan-3-one)
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PDB for NP0337386 (8-Mercapto-p-menthan-3-one)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -5.688  -4.935   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.021  -5.705   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.021  -7.245   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.688  -8.015   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.354  -7.245   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.354  -5.705   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.688  -3.395   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.020  -8.015   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.688  -9.555   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      -4.354 -10.325   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0      -7.021 -10.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.688 -11.095   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    5                                                       
CONECT    7    1                                                            
CONECT    8    5                                                            
CONECT    9    4   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0337386 (8-Mercapto-p-menthan-3-one)
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SMILES for NP0337386 (8-Mercapto-p-menthan-3-one)
CC1CCC(C(=O)C1)C(C)(C)S
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INCHI for NP0337386 (8-Mercapto-p-menthan-3-one)
InChI=1/C10H18OS/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-8,12H,4-6H2,1-3H3
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SynonymsNot Available
Chemical FormulaC10H18OS
Average Mass186.3100 Da
Monoisotopic Mass186.10784 Da
IUPAC Name5-methyl-2-(2-sulfanylpropan-2-yl)cyclohexan-1-one
Traditional Namep-mentha-8-thiol-3-one
CAS Registry NumberNot Available
SMILES
CC1CCC(C(=O)C1)C(C)(C)S
InChI Identifier
InChI=1/C10H18OS/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-8,12H,4-6H2,1-3H3
InChI KeyRVOKNSFEAOYULQ-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Alkylthiol
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP2.78ChemAxon
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity54.33 m³·mol⁻¹ChemAxon
Polarizability21.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Graf FMR, Buchhaupt M: Engineering volatile thiol formation in yeast. J Appl Microbiol. 2023 Feb 16;134(2):lxac078. doi: 10.1093/jambio/lxac078. [PubMed:36626784  ] 
  2. Bampidis V, Azimonti G, Bastos ML, Christensen H, Kouba M, Kos Durjava M, Lopez-Alonso M, Lopez Puente S, Marcon F, Mayo B, Pechova A, Petkova M, Ramos F, Sanz Y, Villa RE, Woutersen R, Brantom P, Chesson A, Westendorf J, Gregoretti L, Manini P, Dusemund B: Safety and efficacy of 8-mercapto-p-menthan-3-one and p-menth-1-ene-8-thiol belonging to chemical group 20 when used as flavourings for all animal species. EFSA J. 2019 Jan 16;17(1):e05530. doi: 10.2903/j.efsa.2019.5530. eCollection 2019  Jan. [PubMed:32626076  ]