NP-MRD: Showing NP-Card for 8,9-Dihydroxy-10-isobutyryloxythymol (NP0139269)

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Record Information

Version

2.0

Created at

2022-06-29 19:46:49 UTC

Updated at

2022-06-29 19:46:49 UTC

NP-MRD ID

NP0139269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8,9-Dihydroxy-10-isobutyryloxythymol

Description

2,3-Dihydroxy-2-(2-hydroxy-4-methylphenyl)propyl 2-methylpropanoate belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively. 8,9-Dihydroxy-10-isobutyryloxythymol is found in Aconitum kongboense, Centipeda minima, Eupatorium fortunei and Inula japonica. 2,3-Dihydroxy-2-(2-hydroxy-4-methylphenyl)propyl 2-methylpropanoate 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
   -4.0974   -2.6543    0.6245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1322   -1.5674    0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5555   -0.9315    1.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553    0.0824    1.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    0.5181    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400    1.5753   -0.0942 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0226    2.0008    1.1895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    2.7992   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3740    3.9268   -0.6459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039    1.5501   -0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313    0.7805   -0.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648   -0.5542   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9634   -1.2473   -0.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893   -1.1780    0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4847   -0.5513    1.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890   -1.0270   -0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8938   -0.1591   -1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668    0.2229   -2.3105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954   -1.1745   -0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8651   -3.2998    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0913   -2.2010    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762   -3.2795   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374   -1.2598    2.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2450    0.5330    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677    1.3332    1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    2.5913   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286    2.9733    0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767    4.4840    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3078    2.6169   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8307    1.3874   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9894   -2.2422    0.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565   -0.9259    2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -0.7207    2.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5502    0.5541    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916   -1.9811   -0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332   -0.8095   -1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -0.2395   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9873   -0.2405   -3.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -1.6855   -1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 10  1  0
 10  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 19  1  0
 19 17  2  0
 17 18  1  0
 17  5  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 14 31  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 10 29  1  0
 10 30  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  4 24  1  0
  3 23  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 19 39  1  0
 18 38  1  0
M  END


  Mrv1533004241510112D          

 19 19  0  0  0  0            999 V2000
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.3480    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
    1.4289   -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
    0.7145   -1.2375    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
    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
  2  4  1  0  0  0  0
  4  5  2  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
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139269

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OCC(O)(CO)C1=CC=C(C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O5/c1-9(2)13(17)19-8-14(18,7-15)11-5-4-10(3)6-12(11)16/h4-6,9,15-16,18H,7-8H2,1-3H3

> <INCHI_KEY>
HGIHDUILBYERQC-UHFFFAOYSA-N

> <FORMULA>
C14H20O5

> <MOLECULAR_WEIGHT>
268.309

> <EXACT_MASS>
268.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.410769792749193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydroxy-2-(2-hydroxy-4-methylphenyl)propyl 2-methylpropanoate

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.7037314116666673

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.635598356558653

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.936347016507996

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1651806901563146

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
70.3933

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-2-(2-hydroxy-4-methylphenyl)propyl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.206   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.644   2.516   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   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    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   12                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
2,3-Dihydroxy-2-(2-hydroxy-4-methylphenyl)propyl 2-methylpropanoic acid	Generator

Chemical Formula

C₁₄H₂₀O₅

Average Mass

268.3090 Da

Monoisotopic Mass

268.13107 Da

IUPAC Name

2,3-dihydroxy-2-(2-hydroxy-4-methylphenyl)propyl 2-methylpropanoate

Traditional Name

2,3-dihydroxy-2-(2-hydroxy-4-methylphenyl)propyl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OCC(O)(CO)C1=CC=C(C)C=C1O

InChI Identifier

InChI=1S/C14H20O5/c1-9(2)13(17)19-8-14(18,7-15)11-5-4-10(3)6-12(11)16/h4-6,9,15-16,18H,7-8H2,1-3H3

InChI Key

HGIHDUILBYERQC-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

Species Name	Source	Reference
Aconitum kongboense	LOTUS Database	35616633
Centipeda minima	LOTUS Database	35616633
Eupatorium fortunei	LOTUS Database	35616633
Inula japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Glycerolipid
Toluene
Monocyclic benzene moiety
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aromatic alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
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	0.99	ALOGPS
logP	1.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.94	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.39 m³·mol⁻¹	ChemAxon
Polarizability	28.41 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

14427472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8,9-Dihydroxy-10-isobutyryloxythymol (NP0139269)

MOL for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

3D MOL for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

3D SDF for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

3D-SDF for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

PDB for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

3D PDB for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

SMILES for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

INCHI for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

Structure for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)

3D Structure for NP0139269 (8,9-Dihydroxy-10-isobutyryloxythymol)