NP-MRD: Showing NP-Card for 22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid (NP0192013)

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Record Information

Version

1.0

Created at

2022-09-04 09:07:49 UTC

Updated at

2022-09-04 09:07:49 UTC

NP-MRD ID

NP0192013

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid

Description

22-{[3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid is found in Dioscorea bulbifera and Greigia sphacelata. 22-{[3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231523262D          

 38 38  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
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  3 37  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004231523262D          

 38 38  0  0  0  0            999 V2000
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    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    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
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  5 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192013

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)OCCCCCCCCCCCCCCCCCCCCCC(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H52O6/c1-37-30-27-28(22-24-29(30)33)23-25-32(36)38-26-20-18-16-14-12-10-8-6-4-2-3-5-7-9-11-13-15-17-19-21-31(34)35/h22-25,27,33H,2-21,26H2,1H3,(H,34,35)

> <INCHI_KEY>
RNKDQPOFWZGWEJ-UHFFFAOYSA-N

> <FORMULA>
C32H52O6

> <MOLECULAR_WEIGHT>
532.762

> <EXACT_MASS>
532.376389394

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
67.40520701764186

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid

> <ALOGPS_LOGP>
8.97

> <JCHEM_LOGP>
10.059970281666669

> <ALOGPS_LOGS>
-7.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.867812166992833

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952014383060167

> <JCHEM_PKA_STRONGEST_BASIC>
-4.888712063015675

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
154.63010000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.83e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid

> <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     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -12.003   6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.338   6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.672   6.160   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.005   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.339   6.160   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.673   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      24.006   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.340   6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.674   6.160   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      28.007   6.930   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      26.674   4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -12.003   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    5   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   76    0
END

View in JSmol

Synonyms

Value	Source
22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoate	Generator

Chemical Formula

C₃₂H₅₂O₆

Average Mass

532.7620 Da

Monoisotopic Mass

532.37639 Da

IUPAC Name

22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid

Traditional Name

22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)OCCCCCCCCCCCCCCCCCCCCCC(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C32H52O6/c1-37-30-27-28(22-24-29(30)33)23-25-32(36)38-26-20-18-16-14-12-10-8-6-4-2-3-5-7-9-11-13-15-17-19-21-31(34)35/h22-25,27,33H,2-21,26H2,1H3,(H,34,35)

InChI Key

RNKDQPOFWZGWEJ-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
Dioscorea bulbifera	LOTUS Database	35616633
Greigia sphacelata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen 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	8.97	ALOGPS
logP	10.06	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	154.63 m³·mol⁻¹	ChemAxon
Polarizability	67.41 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid (NP0192013)

MOL for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

3D MOL for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

3D SDF for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

3D-SDF for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

PDB for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

3D PDB for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

SMILES for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

INCHI for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

Structure for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)

3D Structure for NP0192013 (22-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}docosanoic acid)