NP-MRD: Showing NP-Card for (E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid (NP0058530)

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Record Information

Version

1.0

Created at

2022-04-28 03:52:54 UTC

Updated at

2022-04-28 03:52:54 UTC

NP-MRD ID

NP0058530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid

Description

(2E)-3-[3-(2-hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methylprop-2-enoic acid belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. (E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid is found in Cyathus bulleri. Based on a literature review very few articles have been published on (2E)-3-[3-(2-hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methylprop-2-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.7895   -0.5898    1.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -1.0790    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7649   -0.7267   -0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518    0.1577   -0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683    1.5164   -0.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    2.1952   -0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9376    3.5752   -0.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    2.2234   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5996    1.6058    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    2.4547    0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    0.2110   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700   -0.2553    0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5962   -1.5742    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718   -2.1615   -1.2238 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5961   -0.4732   -0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -1.9295   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7813   -1.9822   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7326   -2.3988   -1.6972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083   -2.3552    0.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0158    0.1809    1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117   -1.4401    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7913   -0.2674    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260   -1.1014   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133    1.8152    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3057    2.0668   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369    3.8905    0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584    3.3061    0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928    3.5085    0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5464    2.4260   -0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2522    2.1496    1.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.1357    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137    0.4077   -0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431   -1.4535    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056   -2.3021    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -2.9814   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484   -2.4642    0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819   -2.2741   -1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791   -2.3257   -0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4892   -1.6912    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4 15  2  0
 15 16  1  0
 15 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  5  2  0
  5  6  1  0
  6  7  1  0
  2 17  1  0
 17 19  1  0
 17 18  2  0
  5  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
  8 27  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
 19 39  1  0
M  END


  Mrv1652304282205532D          

 19 19  0  0  0  0            999 V2000
    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
    0.0000   -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 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
   -0.7145    1.2375    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
   -1.4289    2.4750    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 11  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/C1=C(C)C(CCO)=C(C)C=C1CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9-6-12(8-17)14(7-10(2)15(18)19)11(3)13(9)4-5-16/h6-7,16-17H,4-5,8H2,1-3H3,(H,18,19)/b10-7+

> <INCHI_KEY>
SFHSWFPDOAPCEJ-JXMROGBWSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.070420562955924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[3-(2-hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methylprop-2-enoic acid

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
2.3124411983333344

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.970065710751506

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4697477091142055

> <JCHEM_PKA_STRONGEST_BASIC>
-2.407248064437365

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
75.88619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[3-(2-hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methylprop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    4                                                            
CONECT   12    3   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(2E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methylprop-2-enoate	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(2E)-3-[3-(2-hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methylprop-2-enoic acid

Traditional Name

(2E)-3-[3-(2-hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methylprop-2-enoic acid

CAS Registry Number

Not Available

SMILES

C\C(=C/C1=C(C)C(CCO)=C(C)C=C1CO)C(O)=O

InChI Identifier

InChI=1S/C15H20O4/c1-9-6-12(8-17)14(7-10(2)15(18)19)11(3)13(9)4-5-16/h6-7,16-17H,4-5,8H2,1-3H3,(H,18,19)/b10-7+

InChI Key

SFHSWFPDOAPCEJ-JXMROGBWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cyathus bulleri	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acids

Direct Parent

Cinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Benzyl alcohol
M-xylene
Xylene
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Primary alcohol
Aromatic alcohol
Hydrocarbon derivative
Carbonyl group
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	1.49	ALOGPS
logP	2.31	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.89 m³·mol⁻¹	ChemAxon
Polarizability	29.07 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

C00011935

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

163184528

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid (NP0058530)

MOL for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

3D MOL for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

3D SDF for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

3D-SDF for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

PDB for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

3D PDB for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

SMILES for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

INCHI for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

Structure for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)

3D Structure for NP0058530 ((E)-3-[3-(2-Hydroxyethyl)-6-(hydroxymethyl)-2,4-dimethylphenyl]-2-methyl-2-propenoic acid)