NP-MRD: Showing NP-Card for Docosyl-3,4-dihydroxy-trans-cinnamate (NP0076454)

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Record Information

Version

2.0

Created at

2022-04-28 21:37:11 UTC

Updated at

2022-04-28 21:37:11 UTC

NP-MRD ID

NP0076454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Docosyl-3,4-dihydroxy-trans-cinnamate

Description

Docosyl 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. Docosyl-3,4-dihydroxy-trans-cinnamate is found in Acer triflorum, Glycyrrhiza glabra , Halocnemum strobilaceum and Myoschilos oblongum. It was first documented in 2008 (PMID: 18652347). Based on a literature review a significant number of articles have been published on Docosyl caffeate (PMID: 35490355) (PMID: 35490354) (PMID: 35490353) (PMID: 35490352) (PMID: 35490351) (PMID: 19921583).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223372D          

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M  END

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M  END


  Mrv1652304282223372D          

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   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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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  1  0  0  0  0
  3 34  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076454

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H52O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-26-35-31(34)25-23-28-22-24-29(32)30(33)27-28/h22-25,27,32-33H,2-21,26H2,1H3/b25-23+

> <INCHI_KEY>
GUWHMEMJBCLEBP-WJTDDFOZSA-N

> <FORMULA>
C31H52O4

> <MOLECULAR_WEIGHT>
488.753

> <EXACT_MASS>
488.386560154

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
64.29590292682266

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
9.78

> <JCHEM_LOGP>
11.234317990666668

> <ALOGPS_LOGS>
-7.02

> <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>
148.48240000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.63e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
docosyl (2E)-3-(3,4-dihydroxyphenyl)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  C   UNK     0      36.009   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      37.343   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4   34                                                  
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   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34    3                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

View in JSmol

Synonyms

Value	Source
Docosyl caffeic acid	Generator

Chemical Formula

C₃₁H₅₂O₄

Average Mass

488.7530 Da

Monoisotopic Mass

488.38656 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C31H52O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-26-35-31(34)25-23-28-22-24-29(32)30(33)27-28/h22-25,27,32-33H,2-21,26H2,1H3/b25-23+

InChI Key

GUWHMEMJBCLEBP-WJTDDFOZSA-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
Acer triflorum	LOTUS Database	35616633
Glycyrrhiza glabra	Plant	KNApSAcK
Halocnemum strobilaceum	Plant	KNApSAcK
Myoschilos oblongum	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	9.78	ALOGPS
logP	11.23	ChemAxon
logS	-7	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	24	ChemAxon
Refractivity	148.48 m³·mol⁻¹	ChemAxon
Polarizability	64.3 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

C00039038

Chemspider ID

4475900

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316952

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Baumbusch J, Blakey EP, Carapellotti AM, Dohmen M, Fick DM, Kagan SH, Melendez-Torres GJ, Morgan BE, Munsterman E, Resnick B, Young HM: Nurses and the decade of healthy ageing: An unprecedented opportunity. Int J Older People Nurs. 2022 May;17(3):e12469. doi: 10.1111/opn.12469. [PubMed:35490355 ]
Hill NL, Bratlee-Whitaker E, Wion RK, Madrigal C, Bhargava S, Mogle J: Factors that influence the emotional impact of memory problems in older adults: A qualitative descriptive study. Int J Older People Nurs. 2022 May;17(3):e12439. doi: 10.1111/opn.12439. Epub 2021 Dec 8. [PubMed:35490354 ]
Polastri M, Loforte A, Swol J: "Racing team" or "orchestra" approach? Two different perspectives on providing care in emergency and critical settings. Artif Organs. 2022 May 1. doi: 10.1111/aor.14274. [PubMed:35490353 ]
Wei YF, Wang L, Xia ZY, Gou M, Sun ZY, Lv WF, Tang YQ: Microbial communities in crude oil phase and filter-graded aqueous phase from a Daqing oilfield after polymer flooding. J Appl Microbiol. 2022 May 1. doi: 10.1111/jam.15603. [PubMed:35490352 ]
Authors unspecified: CORRIGENDUM. Transbound Emerg Dis. 2022 May 1. doi: 10.1111/tbed.14572. [PubMed:35490351 ]
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 ]
Wang Q, Zhang CF, Zhang M, Wang ZT: [Study on chemical constituents in roots and rhizomes of Ligularia duciforms II]. Zhongguo Zhong Yao Za Zhi. 2008 May;33(9):1018-20. [PubMed:18652347 ]
Niu F, Zhang B, Du Y, Hu D, Ma S, Feng ZJ, Zhang Y, Pan W: Effect of microcrystalline cellulose under different hydrolysis durations on the stability of thyme oil emulsion. J Food Sci. 2022 Jun;87(6):2707-2717. doi: 10.1111/1750-3841.16154. Epub 2022 May 1. [PubMed:35490350 ]
Arnold F, Wobser R, Kalbhenn J, Westermann L: Integration of sustained low-efficiency dialysis into extracorporeal membrane oxygenation circuit in critically ill COVID-19 patients-A feasibility study. Artif Organs. 2022 May 1. doi: 10.1111/aor.14277. [PubMed:35490349 ]
Lavryk OA, Bandi B, Shawki SF, Floruta C, Xue J, Valente MA, Steele SR, Hull TL: Turnbull-Cutait abdominoperineal pull-through operation: The Cleveland Clinic experience in the 21st century. Colorectal Dis. 2022 May 1. doi: 10.1111/codi.16163. [PubMed:35490348 ]

Showing NP-Card for Docosyl-3,4-dihydroxy-trans-cinnamate (NP0076454)

MOL for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

3D MOL for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

3D SDF for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

3D-SDF for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

PDB for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

3D PDB for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

SMILES for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

INCHI for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

Structure for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)

3D Structure for NP0076454 (Docosyl-3,4-dihydroxy-trans-cinnamate)