NP-MRD: Showing NP-Card for pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0320205)

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Record Information

Version

2.0

Created at

2022-09-11 21:43:45 UTC

Updated at

2022-09-11 21:43:45 UTC

NP-MRD ID

NP0320205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

Pentacosanyl 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. pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Sophora tetraptera. Based on a literature review very few articles have been published on Pentacosanyl caffeate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223432D          

 38 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112223432D          

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   17.8618  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354  -17.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499  -16.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2933  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0078  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7223  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7223  -18.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4367  -18.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0078  -18.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0078  -19.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2933  -18.5625    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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
  9 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  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 31 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320205

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C34H58O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-29-38-34(37)28-26-31-25-27-32(35)33(36)30-31/h25-28,30,35-36H,2-24,29H2,1H3/b28-26+

> <INCHI_KEY>
FVFCQHVXXOWKMY-BYCLXTJYSA-N

> <FORMULA>
C34H58O4

> <MOLECULAR_WEIGHT>
530.834

> <EXACT_MASS>
530.433510348

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
70.68823184629754

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
12.56802398566667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.612491850866324

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20864393932515

> <JCHEM_PKA_STRONGEST_BASIC>
-6.28375993218878

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
162.28539999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      16.004 -32.340   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.338 -33.110   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.672 -32.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.005 -33.110   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.339 -32.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.673 -33.110   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.006 -32.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.340 -33.110   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.674 -32.340   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.007 -33.110   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.341 -32.340   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.675 -33.110   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.008 -32.340   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.342 -33.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.676 -32.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.009 -33.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.343 -32.340   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.677 -33.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.010 -32.340   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.344 -33.110   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      42.678 -32.340   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      44.011 -33.110   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.345 -32.340   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      46.679 -33.110   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      48.012 -32.340   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      49.346 -33.110   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      50.680 -32.340   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      50.680 -30.800   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      52.013 -33.110   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      53.347 -32.340   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      54.681 -33.110   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      56.015 -32.340   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      57.348 -33.110   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      57.348 -34.650   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      58.682 -35.420   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      56.015 -35.420   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      56.015 -36.960   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      54.681 -34.650   0.000  0.00  0.00           C+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                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   31                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   76    0
END

View in JSmol

Synonyms

Value	Source
Pentacosanyl caffeic acid	Generator

Chemical Formula

C₃₄H₅₈O₄

Average Mass

530.8340 Da

Monoisotopic Mass

530.43351 Da

IUPAC Name

pentacosyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

pentacosyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C34H58O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-29-38-34(37)28-26-31-25-27-32(35)33(36)30-31/h25-28,30,35-36H,2-24,29H2,1H3/b28-26+

InChI Key

FVFCQHVXXOWKMY-BYCLXTJYSA-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
Sophora tetraptera	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
logP	12.57	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	162.29 m³·mol⁻¹	ChemAxon
Polarizability	70.69 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

101928789

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0320205)

MOL for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0320205 (pentacosyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)