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Showing NP-Card for 3-Sulfanylhexan-1-ol (NP0083787)

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Record Information
Version2.0
Created at2022-04-29 04:43:28 UTC
Updated at2022-04-29 04:43:28 UTC
NP-MRD IDNP0083787
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Sulfanylhexan-1-ol
Description3-Mercapto-1-hexanol, also known as 3-sulfanyl-1-hexanol or fema 3850, belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. Thus, 3-mercapto-1-hexanol is considered to be a fatty alcohol lipid molecule. 3-Mercapto-1-hexanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Mercapto-1-hexanol is a sulfur tasting compound. Outside of the human body, 3-Mercapto-1-hexanol has been detected, but not quantified in, fruits. This could make 3-mercapto-1-hexanol a potential biomarker for the consumption of these foods. 3-Sulfanylhexan-1-ol is found in Humulus lupulus , Passiflora edulis and Vitis vinifera. 3-Sulfanylhexan-1-ol was first documented in 2003 (PMID: 12769536). An alkanethiol that is hexane substituted at positions 1 and 3 by hydroxy and sulfanyl groups respectively (PMID: 21332202) (PMID: 21854044) (PMID: 22663147) (PMID: 22868118).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083787 (3-Sulfanylhexan-1-ol)


  Mrv0541 02241209212D          

  8  7  0  0  0  0            999 V2000
    1.0721   -1.0721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.1646    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    0.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for NP0083787 (3-Sulfanylhexan-1-ol)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
    2.2678    1.0796    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938   -0.2147   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -0.3800   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2266   -0.3459    0.6039 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4222   -1.7347    1.5924 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026   -0.5796    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3706    0.4411   -0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631    1.7330    0.0313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628    0.9009    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2535    1.4537    0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4314    1.7710    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3581   -1.0333    0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -0.2494   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4123   -1.4079   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676    0.3320   -1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073    0.6068    1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694   -2.9173    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563   -1.5696    0.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523   -0.5675    1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    0.3159   -1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4439    0.1818   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184    2.1843   -0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  1
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
M  END
Download

3D SDF for NP0083787 (3-Sulfanylhexan-1-ol)


  Mrv0541 02241209212D          

  8  7  0  0  0  0            999 V2000
    1.0721   -1.0721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.1646    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    0.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083787

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(S)CCO

> <INCHI_IDENTIFIER>
InChI=1S/C6H14OS/c1-2-3-6(8)4-5-7/h6-8H,2-5H2,1H3

> <INCHI_KEY>
TYZFMFVWHZKYSE-UHFFFAOYSA-N

> <FORMULA>
C6H14OS

> <MOLECULAR_WEIGHT>
134.24

> <EXACT_MASS>
134.07653576

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
15.96473404470777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-sulfanylhexan-1-ol

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
1.3825381746666667

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.00248009447285

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.046418413624375

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3882615412357753

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
39.0406

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-sulfanylhexan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0083787 (3-Sulfanylhexan-1-ol)

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PDB for NP0083787 (3-Sulfanylhexan-1-ol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       2.001  -2.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.615  -2.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.615  -2.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.615  -0.461   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      -2.001   0.307   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       0.615   0.307   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.769   1.847   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.615   2.771   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0083787 (3-Sulfanylhexan-1-ol)
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SMILES for NP0083787 (3-Sulfanylhexan-1-ol)
CCCC(S)CCO
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INCHI for NP0083787 (3-Sulfanylhexan-1-ol)
InChI=1S/C6H14OS/c1-2-3-6(8)4-5-7/h6-8H,2-5H2,1H3
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Synonyms
ValueSource
3-Mercaptohexan-1-olChEBI
3-Sulfanyl-1-hexanolChEBI
3-Sulphanylhexan-1-olChEBI
3-Sulphanyl-1-hexanolGenerator
3-Sulfanylhexan-1-olGenerator
3-Mercapto hexan-1-olHMDB
3-MercaptohexanolHMDB
FEMA 3850HMDB
3-Mercapto-1-hexanolChEBI
Chemical FormulaC6H14OS
Average Mass134.2400 Da
Monoisotopic Mass134.07654 Da
IUPAC Name3-sulfanylhexan-1-ol
Traditional Name3-sulfanylhexan-1-ol
CAS Registry NumberNot Available
SMILES
CCCC(S)CCO
InChI Identifier
InChI=1S/C6H14OS/c1-2-3-6(8)4-5-7/h6-8H,2-5H2,1H3
InChI KeyTYZFMFVWHZKYSE-UHFFFAOYSA-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
Humulus lupulusPlant
Passiflora edulisLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassThiols  
Sub ClassAlkylthiols  
Direct ParentAlkylthiols  
Alternative Parents
Substituents
  • Alkylthiol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP2.06ALOGPS
logP1.38ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.05ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.04 m³·mol⁻¹ChemAxon
Polarizability15.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040152  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019857  
KNApSAcK IDNot Available
Chemspider ID454763  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound521348  
PDB IDNot Available
ChEBI ID77690  
Good Scents IDNot Available
References
General References
  1. Vermeulen C, Guyot-Declerck C, Collin S: Combinatorial synthesis and sensorial properties of mercapto primary alcohols and analogues. J Agric Food Chem. 2003 Jun 4;51(12):3623-8. doi: 10.1021/jf0212340. [PubMed:12769536  ] 
  2. Ugliano M, Kwiatkowski M, Vidal S, Capone D, Siebert T, Dieval JB, Aagaard O, Waters EJ: Evolution of 3-mercaptohexanol, hydrogen sulfide, and methyl mercaptan during bottle storage of Sauvignon blanc wines. Effect of glutathione, copper, oxygen exposure, and closure-derived oxygen. J Agric Food Chem. 2011 Mar 23;59(6):2564-72. doi: 10.1021/jf1043585. Epub 2011 Feb 18. [PubMed:21332202  ] 
  3. Allen T, Herbst-Johnstone M, Girault M, Butler P, Logan G, Jouanneau S, Nicolau L, Kilmartin PA: Influence of grape-harvesting steps on varietal thiol aromas in Sauvignon blanc wines. J Agric Food Chem. 2011 Oct 12;59(19):10641-50. doi: 10.1021/jf2018676. Epub 2011 Sep 8. [PubMed:21854044  ] 
  4. Benkwitz F, Nicolau L, Lund C, Beresford M, Wohlers M, Kilmartin PA: Evaluation of key odorants in sauvignon blanc wines using three different methodologies. J Agric Food Chem. 2012 Jun 27;60(25):6293-302. doi: 10.1021/jf300914n. Epub 2012 Jun 18. [PubMed:22663147  ] 
  5. Makhotkina O, Kilmartin PA: Hydrolysis and formation of volatile esters in New Zealand Sauvignon blanc wine. Food Chem. 2012 Nov 15;135(2):486-93. doi: 10.1016/j.foodchem.2012.05.034. Epub 2012 May 11. [PubMed:22868118  ]