NP-MRD: Showing NP-Card for Eicosanyl-trans-p-coumarate (NP0073458)

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Record Information

Version

2.0

Created at

2022-04-28 18:42:28 UTC

Updated at

2022-04-28 18:42:29 UTC

NP-MRD ID

NP0073458

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eicosanyl-trans-p-coumarate

Description

Eicosyl p-coumarate belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Eicosanyl-trans-p-coumarate is found in Artemisia igniaria, Crepis vesicaria, Juniperus brevifolia, Psiadia punctulata, Tanacetum densum and Tanacetum longifolium. Based on a literature review very few articles have been published on eicosyl p-coumarate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220422D          

 32 32  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282220422D          

 32 32  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0073458

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCOC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26-32-29(31)25-22-27-20-23-28(30)24-21-27/h20-25,30H,2-19,26H2,1H3/b25-22+

> <INCHI_KEY>
NTXQDNOGQGBPCH-YYDJUVGSSA-N

> <FORMULA>
C29H48O3

> <MOLECULAR_WEIGHT>
444.7

> <EXACT_MASS>
444.360345406

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
59.07458687357721

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
icosyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
9.88

> <JCHEM_LOGP>
10.648745982333335

> <ALOGPS_LOGS>
-7.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398661260312752

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9547309780583015

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
137.29950000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.64e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
icosyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.006   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.340   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.674   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      28.007   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.341   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.675   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.008   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      33.342   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      34.676   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   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                                                            
CONECT   32    2                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
Eicosyl p-coumaric acid	Generator

Chemical Formula

C₂₉H₄₈O₃

Average Mass

444.7000 Da

Monoisotopic Mass

444.36035 Da

IUPAC Name

icosyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

icosyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCOC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C29H48O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26-32-29(31)25-22-27-20-23-28(30)24-21-27/h20-25,30H,2-19,26H2,1H3/b25-22+

InChI Key

NTXQDNOGQGBPCH-YYDJUVGSSA-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
Artemisia igniaria	LOTUS Database	35616633
Crepis vesicaria	LOTUS Database	35616633
Juniperus brevifolia	Plant	KNApSAcK
Psiadia punctulata	LOTUS Database	35616633
Tanacetum densum	LOTUS Database	35616633
Tanacetum longifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Fatty alcohol ester
Cinnamic acid ester
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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	9.88	ALOGPS
logP	10.65	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	137.3 m³·mol⁻¹	ChemAxon
Polarizability	59.07 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

C00033803

Chemspider ID

10186468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15139446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Eicosanyl-trans-p-coumarate (NP0073458)

MOL for NP0073458 (Eicosanyl-trans-p-coumarate)

3D MOL for NP0073458 (Eicosanyl-trans-p-coumarate)

3D SDF for NP0073458 (Eicosanyl-trans-p-coumarate)

3D-SDF for NP0073458 (Eicosanyl-trans-p-coumarate)

PDB for NP0073458 (Eicosanyl-trans-p-coumarate)

3D PDB for NP0073458 (Eicosanyl-trans-p-coumarate)

SMILES for NP0073458 (Eicosanyl-trans-p-coumarate)

INCHI for NP0073458 (Eicosanyl-trans-p-coumarate)

Structure for NP0073458 (Eicosanyl-trans-p-coumarate)

3D Structure for NP0073458 (Eicosanyl-trans-p-coumarate)