NP-MRD: Showing NP-Card for [2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone (NP0144231)

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Record Information

Version

2.0

Created at

2022-09-01 23:08:00 UTC

Updated at

2022-09-01 23:08:00 UTC

NP-MRD ID

NP0144231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone

Description

Resorthiomycin belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Resorthiomycin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    4.8735    2.9521   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371    2.3011   -0.2428 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    0.5224   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -0.0145   -0.2914 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363   -0.2846    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7678    0.2776    0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828    1.7586    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3589   -0.5306    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6756    0.0706    0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822    0.4803   -0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7243    1.1157   -0.3257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6913    0.2377    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5836    2.3742    0.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2236   -1.9110    0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2751   -2.7692    0.7496 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0139   -2.4499    0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1441   -3.9499    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547   -1.6575    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3013   -2.3884    0.0086 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3695    2.4754   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4831    2.9397    0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7581    4.0320   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261    2.2334    1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8693    2.1935   -0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870    2.0491    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5971    0.9528    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2897   -0.6408    1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824    1.1923   -1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -0.3591   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1620    1.3008   -1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755   -0.6771    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529   -0.0991   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1870    0.8691    1.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3175    2.9388   -0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2071   -2.5235    0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5731   -4.3583    1.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021   -4.2218    0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090   -4.3551   -0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944   -2.0767   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  6
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
M  END


  Mrv1533004231518222D          

 19 19  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 S   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
    1.4289    2.4750    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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 O   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
   -0.7145   -0.4125    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    1.2375    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC(=O)C1=C(C)C(CCC(C)O)=C(O)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O4S/c1-7(15)5-6-10-8(2)11(14(18)19-4)13(17)9(3)12(10)16/h7,15-17H,5-6H2,1-4H3

> <INCHI_KEY>
YIKHKZNDXADDGL-UHFFFAOYSA-N

> <FORMULA>
C14H20O4S

> <MOLECULAR_WEIGHT>
284.37

> <EXACT_MASS>
284.108230298

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.91127299152498

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
4.183519549666667

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.438912343534474

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.477724666324344

> <JCHEM_PKA_STRONGEST_BASIC>
-2.51327065198946

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
79.0139

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       0.000   4.620   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
6-Acetyl-4-(3-hydroxybutyl)-2-methyl-5-methylthioresorcinol	MeSH

Chemical Formula

C₁₄H₂₀O₄S

Average Mass

284.3700 Da

Monoisotopic Mass

284.10823 Da

IUPAC Name

[2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone

Traditional Name

[2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone

CAS Registry Number

Not Available

SMILES

CSC(=O)C1=C(C)C(CCC(C)O)=C(O)C(C)=C1O

InChI Identifier

InChI=1S/C14H20O4S/c1-7(15)5-6-10-8(2)11(14(18)19-4)13(17)9(3)12(10)16/h7,15-17H,5-6H2,1-4H3

InChI Key

YIKHKZNDXADDGL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acid and derivatives

Alternative Parents

Substituents

Salicylic acid or derivatives
P-xylenol
Xylenol
Thiobenzoic acid or derivatives
Benzoyl
O-cresol
P-xylene
Xylene
M-cresol
Resorcinol
Phenol
Vinylogous acid
Carbothioic s-ester
Thiocarboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Sulfenyl compound
Thiocarboxylic acid or derivatives
Alcohol
Organosulfur compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.86	ALOGPS
logP	4.18	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.01 m³·mol⁻¹	ChemAxon
Polarizability	30.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone (NP0144231)

MOL for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

3D MOL for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

3D SDF for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

3D-SDF for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

PDB for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

3D PDB for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

SMILES for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

INCHI for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

Structure for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)

3D Structure for NP0144231 ([2,4-dihydroxy-5-(3-hydroxybutyl)-3,6-dimethylphenyl](methylsulfanyl)methanone)