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Showing NP-Card for 3-Mercaptohexyl acetate (NP0335034)

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Record Information
Version2.0
Created at2024-09-10 23:35:38 UTC
Updated at2024-09-10 23:35:38 UTC
NP-MRD IDNP0335034
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Mercaptohexyl acetate
Description3-Mercaptohexyl acetate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3-Mercaptohexyl acetate was first documented in 2016 (PMID: 27688176). Based on a literature review a significant number of articles have been published on 3-mercaptohexyl acetate (PMID: 30387351) (PMID: 38012999) (PMID: 34399457) (PMID: 33281489) (PMID: 31108790) (PMID: 30097818).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335034 (3-Mercaptohexyl acetate)


  Mrv2104 05262302072D          

 11 10  0  0  0  0            999 V2000
   -3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -2.9684    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
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3D MOL for NP0335034 (3-Mercaptohexyl acetate)

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3D SDF for NP0335034 (3-Mercaptohexyl acetate)

  Mrv2104 05262302072D          

 11 10  0  0  0  0            999 V2000
   -3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -2.9684    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335034

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(S)CCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1/C8H16O2S/c1-3-4-8(11)5-6-10-7(2)9/h8,11H,3-6H2,1-2H3

> <INCHI_KEY>
JUCARGIKESIVLB-UHFFFAOYNA-N

> <FORMULA>
C8H16O2S

> <MOLECULAR_WEIGHT>
176.27

> <EXACT_MASS>
176.087100929

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.178163020418147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-sulfanylhexyl acetate

> <JCHEM_LOGP>
1.8236635849999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.04614512034316

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9938913665179205

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
48.1921

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-sulfanylhexyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0335034 (3-Mercaptohexyl acetate)
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PDB for NP0335034 (3-Mercaptohexyl acetate)
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      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.946  -3.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.389  -3.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.055  -4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.612  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.723  -4.001   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.612  -5.541   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.278  -3.231   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      -2.723  -5.541   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    7                                                            
CONECT    3    1    4                                                       
CONECT    4    3    8                                                       
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7    2    9   10                                                  
CONECT    8    4    5   11                                                  
CONECT    9    7                                                            
CONECT   10    6    7                                                       
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0335034 (3-Mercaptohexyl acetate)
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SMILES for NP0335034 (3-Mercaptohexyl acetate)
CCCC(S)CCOC(C)=O
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INCHI for NP0335034 (3-Mercaptohexyl acetate)
InChI=1/C8H16O2S/c1-3-4-8(11)5-6-10-7(2)9/h8,11H,3-6H2,1-2H3
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Synonyms
ValueSource
3-Mercaptohexyl acetic acidGenerator
Chemical FormulaC8H16O2S
Average Mass176.2700 Da
Monoisotopic Mass176.08710 Da
IUPAC Name3-sulfanylhexyl acetate
Traditional Name3-sulfanylhexyl acetate
CAS Registry NumberNot Available
SMILES
CCCC(S)CCOC(C)=O
InChI Identifier
InChI=1/C8H16O2S/c1-3-4-8(11)5-6-10-7(2)9/h8,11H,3-6H2,1-2H3
InChI KeyJUCARGIKESIVLB-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP1.82ChemAxon
pKa (Strongest Acidic)10.05ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.19 m³·mol⁻¹ChemAxon
Polarizability20.18 ųChemAxon
Number of Rings0ChemAxon
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 ID77818  
Good Scents IDNot Available
References
General References
  1. Zhu J, Xiao Z: Characterization of Odor-Active Volatiles in Hawthorn Puree Using Thermal Desorption System Coupled to Gas Chromatography-Mass Spectrometry-Olfactometry and GC-Flame Photometric Detector. J Agric Food Chem. 2018 Nov 21;66(46):12296-12305. doi: 10.1021/acs.jafc.8b04636.  Epub 2018 Nov 9. [PubMed:30387351  ] 
  2. Api AM, Belsito D, Botelho D, Bruze M, Burton GA Jr, Cancellieri MA, Chon H, Dagli ML, Dekant W, Deodhar C, Fryer AD, Jones L, Joshi K, Kumar M, Lapczynski A, Lavelle M, Lee I, Liebler DC, Moustakas H, Na M, Penning TM, Ritacco G, Romine J, Sadekar N, Schultz TW, Selechnik D, Siddiqi F, Sipes IG, Sullivan G, Thakkar Y, Tokura Y: RIFM fragrance ingredient safety assessment, 3-mercaptohexyl acetate, CAS Registry Number 136954-20-6. Food Chem Toxicol. 2023 Dec;182 Suppl 1:114223. doi: 10.1016/j.fct.2023.114223.  Epub 2023 Nov 25. [PubMed:38012999  ] 
  3. Niu Y, Deng J, Xiao Z, Zhu J: Characterization of the major aroma-active compounds in peach (Prunus persica L. Batsch) by gas chromatography-olfactometry, flame photometric detection and molecular sensory science approaches. Food Res Int. 2021 Sep;147:110457. doi: 10.1016/j.foodres.2021.110457. Epub 2021  Jun 5. [PubMed:34399457  ] 
  4. Zabukovec P, Cadez N, Cus F: Isolation and Identification of Indigenous Wine Yeasts and Their Use in Alcoholic Fermentation. Food Technol Biotechnol. 2020 Sep;58(3):337-347. doi: 10.17113/ftb.58.03.20.6677. [PubMed:33281489  ] 
  5. Wilson C, Brand J, du Toit W, Buica A: Matrix effects influencing the perception of 3-mercaptohexan-1-ol (3MH) and 3-mercaptohexyl acetate (3MHA) in different Chenin Blanc wines by Projective Mapping (PM) with Ultra Flash profiling (UFP) intensity ratings. Food Res Int. 2019 Jul;121:633-640. doi: 10.1016/j.foodres.2018.12.032. Epub 2018  Dec 25. [PubMed:31108790  ] 
  6. Deroite A, Legras JL, Rigou P, Ortiz-Julien A, Dequin S: Lipids modulate acetic acid and thiol final concentrations in wine during fermentation by Saccharomyces cerevisiae x Saccharomyces kudriavzevii hybrids. AMB Express. 2018 Aug 10;8(1):130. doi: 10.1186/s13568-018-0657-5. [PubMed:30097818  ] 
  7. Bonnaffoux H, Delpech S, Remond E, Schneider R, Roland A, Cavelier F: Revisiting the evaluation strategy of varietal thiol biogenesis. Food Chem. 2018 Dec 1;268:126-133. doi: 10.1016/j.foodchem.2018.06.061. Epub 2018  Jun 15. [PubMed:30064739  ] 
  8. Zhu J, Xiao Z: Characterization of the Major Odor-Active Compounds in Dry Jujube Cultivars by Application of Gas Chromatography-Olfactometry and Odor Activity Value. J Agric Food Chem. 2018 Jul 25;66(29):7722-7734. doi: 10.1021/acs.jafc.8b01366.  Epub 2018 Jun 5. [PubMed:29790345  ] 
  9. Zhu J, Wang L, Xiao Z, Niu Y: Characterization of the key aroma compounds in mulberry fruits by application of gas chromatography-olfactometry (GC-O), odor activity value (OAV), gas chromatography-mass spectrometry (GC-MS) and flame photometric detection (FPD). Food Chem. 2018 Apr 15;245:775-785. doi: 10.1016/j.foodchem.2017.11.112. Epub  2017 Dec 2. [PubMed:29287440  ] 
  10. Alegre Y, Cullere L, Ferreira V, Hernandez-Orte P: Study of the influence of varietal amino acid profiles on the polyfunctional mercaptans released from their precursors. Food Res Int. 2017 Oct;100(Pt 1):740-747. doi: 10.1016/j.foodres.2017.07.081.  Epub 2017 Aug 2. [PubMed:28873745  ] 
  11. Roland A, Delpech S, Dagan L, Ducasse MA, Cavelier F, Schneider R: Innovative analysis of 3-mercaptohexan-1-ol, 3-mercaptohexylacetate and their corresponding disulfides in wine by stable isotope dilution assay and nano-liquid chromatography tandem mass spectrometry. J Chromatogr A. 2016 Oct 14;1468:154-163. doi: 10.1016/j.chroma.2016.09.043. Epub  2016 Sep 21. [PubMed:27688176  ] 
  12. Casu F, Pinu FR, Fedrizzi B, Greenwood DR, Villas-Boas SG: The effect of linoleic acid on the Sauvignon blanc fermentation by different wine yeast strains. FEMS Yeast Res. 2016 Aug;16(5):fow050. doi: 10.1093/femsyr/fow050. Epub 2016 Jun  30. [PubMed:27364827  ] 
  13. Saenz-Navajas MP, Alegre Y, de-la-Fuente A, Ferreira V, Garcia D, Eizaguirre S, Razquin I, Hernandez-Orte P: Rapid sensory-directed methodology for the selection of high-quality aroma wines. J Sci Food Agric. 2016 Sep;96(12):4250-62. doi: 10.1002/jsfa.7636. Epub 2016 Feb  15. [PubMed:26799922  ]