NP-MRD: Showing NP-Card for Ethyl 3,4-dicaffeoylquinate (NP0138892)

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Record Information

Version

1.0

Created at

2022-06-29 19:21:59 UTC

Updated at

2022-06-29 19:21:59 UTC

NP-MRD ID

NP0138892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ethyl 3,4-dicaffeoylquinate

Description

Ethyl 3,4-dicaffeoylquinate belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. It was first documented in 1993 (PMID: 35862567). Based on a literature review a significant number of articles have been published on ethyl 3,4-dicaffeoylquinate (PMID: 35863886) (PMID: 35863885) (PMID: 25172103) (PMID: 20822012).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221222D          

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M  END

     RDKit          3D

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  Mrv1652306292221222D          

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 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
  9 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 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
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 33 36  1  0  0  0  0
 32 37  1  0  0  0  0
  8 38  1  1  0  0  0
  6 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0138892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)[C@]1(O)C[C@@H](O)[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H](C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O12/c1-2-37-26(35)27(36)13-21(32)25(39-24(34)10-6-16-4-8-18(29)20(31)12-16)22(14-27)38-23(33)9-5-15-3-7-17(28)19(30)11-15/h3-12,21-22,25,28-32,36H,2,13-14H2,1H3/b9-5+,10-6+/t21-,22-,25-,27+/m1/s1

> <INCHI_KEY>
RGAMPVVUXFUXES-FYOODVSHSA-N

> <FORMULA>
C27H28O12

> <MOLECULAR_WEIGHT>
544.509

> <EXACT_MASS>
544.158076342

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.608994240190306

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (1S,3R,4R,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylate

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.660932327333333

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.508604020092859

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.907347662124694

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2468837188713318

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
136.28190000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (1S,3R,4R,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylate

> <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      -1.012  -5.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.505  -4.838   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.495  -6.018   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.011  -5.750   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.538  -4.303   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       9.336 -19.250   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       4.991  -5.750   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11   39                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   38                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    6                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24   19                                                            
CONECT   25    9   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   33                                                            
CONECT   37   32                                                            
CONECT   38    8                                                            
CONECT   39    6                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 3,4-dicaffeoylquinic acid	Generator

Chemical Formula

C₂₇H₂₈O₁₂

Average Mass

544.5090 Da

Monoisotopic Mass

544.15808 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

143051-73-4

SMILES

CCOC(=O)[C@]1(O)C[C@@H](O)[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H](C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C27H28O12/c1-2-37-26(35)27(36)13-21(32)25(39-24(34)10-6-16-4-8-18(29)20(31)12-16)22(14-27)38-23(33)9-5-15-3-7-17(28)19(30)11-15/h3-12,21-22,25,28-32,36H,2,13-14H2,1H3/b9-5+,10-6+/t21-,22-,25-,27+/m1/s1

InChI Key

RGAMPVVUXFUXES-FYOODVSHSA-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 quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
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

8729931

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10554540

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Morales Corado JA, Lee CU, Enns GM: Carnitine-Acylcarnitine Translocase Deficiency. 1993. [PubMed:35862567 ]
Kaorop W, Maneechote C, Kumfu S, Chattipakorn SC, Chattipakorn N: Mitochondrial-derived peptides as a novel intervention for obesity and cardiac diseases: bench evidence for potential bedside application. J Clin Pathol. 2022 Jul 21. pii: jcp-2022-208321. doi: 10.1136/jcp-2022-208321. [PubMed:35863886 ]
Zheng T, Zheng S, Wang K, Quan H, Bai Q, Li S, Qi R, Zhao Y, Cui X, Gao X: Automatic CD30 scoring method for whole slide images of primary cutaneous CD30(+) lymphoproliferative diseases. J Clin Pathol. 2022 Jul 21. pii: jcp-2022-208344. doi: 10.1136/jcp-2022-208344. [PubMed:35863885 ]
Chen J, Mangelinckx S, Ma L, Wang Z, Li W, De Kimpe N: Caffeoylquinic acid derivatives isolated from the aerial parts of Gynura divaricata and their yeast alpha-glucosidase and PTP1B inhibitory activity. Fitoterapia. 2014 Dec;99:1-6. doi: 10.1016/j.fitote.2014.08.015. Epub 2014 Aug 27. [PubMed:25172103 ]
Liu J, Ding G, Yu S: [Chemical constituents from stem barks of Vernonia cumingiana]. Zhongguo Zhong Yao Za Zhi. 2010 Jun;35(11):1421-4. [PubMed:20822012 ]

Showing NP-Card for Ethyl 3,4-dicaffeoylquinate (NP0138892)

MOL for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

3D MOL for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

3D SDF for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

3D-SDF for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

PDB for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

3D PDB for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

SMILES for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

INCHI for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

Structure for NP0138892 (Ethyl 3,4-dicaffeoylquinate)

3D Structure for NP0138892 (Ethyl 3,4-dicaffeoylquinate)