NP-MRD: Showing NP-Card for Eicosanyl caffeate (NP0138917)

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Record Information

Version

2.0

Created at

2022-06-29 19:23:09 UTC

Updated at

2022-06-29 19:23:09 UTC

NP-MRD ID

NP0138917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eicosanyl caffeate

Description

Eicosanyl caffeate 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. Eicosanyl caffeate is found in Glycyrrhiza inflata. It was first documented in 2009 (PMID: 19921583). Based on a literature review very few articles have been published on Eicosanyl caffeate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221232D          

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 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 29 32  1  0  0  0  0
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138917

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-33-29(32)23-21-26-20-22-27(30)28(31)25-26/h20-23,25,30-31H,2-19,24H2,1H3/b23-21+

> <INCHI_KEY>
LTSJTDDQUOUKJT-XTQSDGFTSA-N

> <FORMULA>
C29H48O4

> <MOLECULAR_WEIGHT>
460.699

> <EXACT_MASS>
460.355260026

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.43870076567325

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
9.33

> <JCHEM_LOGP>
10.345180660666667

> <ALOGPS_LOGS>
-6.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.612491850866327

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208643939325144

> <JCHEM_PKA_STRONGEST_BASIC>
-6.28375993218878

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
139.2804

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.75e-05 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      14.670 -28.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.004 -27.720   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.338 -28.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.672 -27.720   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.005 -28.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.339 -27.720   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.673 -28.490   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.006 -27.720   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.340 -28.490   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.674 -27.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.007 -28.490   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.341 -27.720   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.675 -28.490   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.008 -27.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.342 -28.490   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.676 -27.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.009 -28.490   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.343 -27.720   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.677 -28.490   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      40.010 -27.720   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      41.344 -28.490   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      42.678 -27.720   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      42.678 -26.180   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      44.011 -28.490   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      45.345 -27.720   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      46.679 -28.490   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      48.012 -27.720   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      49.346 -28.490   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      49.346 -30.030   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      48.012 -30.800   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      46.679 -30.030   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      50.680 -30.800   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      50.680 -27.720   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   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   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   29                                                            
CONECT   33   28                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Value	Source
Eicosanyl caffeic acid	Generator

Chemical Formula

C₂₉H₄₈O₄

Average Mass

460.6990 Da

Monoisotopic Mass

460.35526 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

28593-90-0

SMILES

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

InChI Identifier

InChI=1S/C29H48O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-33-29(32)23-21-26-20-22-27(30)28(31)25-26/h20-23,25,30-31H,2-19,24H2,1H3/b23-21+

InChI Key

LTSJTDDQUOUKJT-XTQSDGFTSA-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
Glycyrrhiza inflata	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
Fatty alcohol ester
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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

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

4478381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320238

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dey S, Deepak M, Setty M, D'Souza P, Agarwal A, Sangli GK: Bioactive caffeic acid esters from Glycyrrhiza glabra. Nat Prod Res. 2009;23(18):1657-63. doi: 10.1080/14786410802134348. [PubMed:19921583 ]

Showing NP-Card for Eicosanyl caffeate (NP0138917)

MOL for NP0138917 (Eicosanyl caffeate)

3D MOL for NP0138917 (Eicosanyl caffeate)

3D SDF for NP0138917 (Eicosanyl caffeate)

3D-SDF for NP0138917 (Eicosanyl caffeate)

PDB for NP0138917 (Eicosanyl caffeate)

3D PDB for NP0138917 (Eicosanyl caffeate)

SMILES for NP0138917 (Eicosanyl caffeate)

INCHI for NP0138917 (Eicosanyl caffeate)

Structure for NP0138917 (Eicosanyl caffeate)

3D Structure for NP0138917 (Eicosanyl caffeate)