NP-MRD: Showing NP-Card for octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0162637)

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Record Information

Version

2.0

Created at

2022-09-02 21:04:41 UTC

Updated at

2022-09-02 21:04:41 UTC

NP-MRD ID

NP0162637

Secondary Accession Numbers

None

Natural Product Identification

Common Name

octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

Z-octadecyl 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. octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate was first documented in 2006 (PMID: 16780156). Based on a literature review very few articles have been published on z-octadecyl caffeate (PMID: 22803368).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022223042D          

 31 31  0  0  0  0            999 V2000
   14.2894   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2933   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2933   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0078   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0078   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2933   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2933   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5788   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
M  END

     RDKit          3D

 75 75  0  0  0  0  0  0  0  0999 V2000
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    5.8415    1.7364   -0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9200    2.4039   -1.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1707    2.2373   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2850    1.8348   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4728    0.7911    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6346    0.3604    1.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8964   -0.7820    2.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0269   -1.5080    2.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2936   -2.6373    2.9441 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9075   -1.1021    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0510   -1.8739    1.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6335    0.0028    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6189   -0.2762   -1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160   -0.9353   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4593    1.0833   -3.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556    2.0173   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8275    2.6909   -2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022223042D          

 31 31  0  0  0  0            999 V2000
   14.2894   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.8644   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0162637

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22-31-27(30)21-19-24-18-20-25(28)26(29)23-24/h18-21,23,28-29H,2-17,22H2,1H3/b21-19-

> <INCHI_KEY>
QYVZEPLDLPYECM-VZCXRCSSSA-N

> <FORMULA>
C27H44O4

> <MOLECULAR_WEIGHT>
432.645

> <EXACT_MASS>
432.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.899805854772445

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octadecyl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
8.77

> <JCHEM_LOGP>
9.456043330666668

> <ALOGPS_LOGS>
-6.53

> <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>
130.07839999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
octadecyl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      26.674  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.007  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.341  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.675  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.008  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.342  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.676  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      36.009  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.343  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.677  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      40.010  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.344  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.678  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      44.011  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      45.345  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      46.679  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      48.012  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      49.346  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      50.680  -1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      52.013  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      52.013  -3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      53.347  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      54.681  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      54.681  -3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      56.015  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      56.015  -6.160   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      54.681  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      54.681  -8.470   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      53.347  -6.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      52.013  -6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      53.347  -4.620   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   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
Z-Octadecyl caffeic acid	Generator
Octadecyl caffeate	MeSH

Chemical Formula

C₂₇H₄₄O₄

Average Mass

432.6450 Da

Monoisotopic Mass

432.32396 Da

IUPAC Name

octadecyl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

octadecyl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H44O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22-31-27(30)21-19-24-18-20-25(28)26(29)23-24/h18-21,23,28-29H,2-17,22H2,1H3/b21-19-

InChI Key

QYVZEPLDLPYECM-VZCXRCSSSA-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

Not Available

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	8.77	ALOGPS
logP	9.46	ChemAxon
logS	-6.5	ALOGPS
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	20	ChemAxon
Refractivity	130.08 m³·mol⁻¹	ChemAxon
Polarizability	53.9 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

124519071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou GX, Yang YC, Shi JG: [Study of chemical constituents in stem rind of Daphne giraldii]. Zhongguo Zhong Yao Za Zhi. 2006 Apr;31(7):555-7. [PubMed:16780156 ]
Chen L, Wang L, Zhang Q, Zhang S, Ye W: [Non-alkaloid chemical constituents from Coptis chinensis]. Zhongguo Zhong Yao Za Zhi. 2012 May;37(9):1241-4. [PubMed:22803368 ]
LOTUS database [Link]

Showing NP-Card for octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0162637)

MOL for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0162637 (octadecyl (2z)-3-(3,4-dihydroxyphenyl)prop-2-enoate)