NP-MRD: Showing NP-Card for 1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid (NP0085288)

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Record Information

Version

2.0

Created at

2022-04-29 05:51:55 UTC

Updated at

2022-04-29 05:51:55 UTC

NP-MRD ID

NP0085288

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid

Description

1,4-Di-O-caffeoylquinic acid, also known as NSC 91529, 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. 1,4-Di-O-caffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,4-Di-O-caffeoylquinic acid has been detected, but not quantified in, herbs and spices and tea. 1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid is found in Helichrysum italicum . This could make 1,4-di-O-caffeoylquinic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241215532D          

 37 39  0  0  0  0            999 V2000
    0.1918   -0.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6175   -0.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9054    0.3727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1907    0.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234   -1.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5238    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387    0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237   -0.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532    0.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  6 35  1  1  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02241215532D          

 37 39  0  0  0  0            999 V2000
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    0.1918   -0.8636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0085288

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(32)36-23-19(30)11-25(24(34)35,12-20(23)31)37-22(33)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-31H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

> <INCHI_KEY>
IYXQRCXQQWUFQV-PSEXTPKNSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.4509

> <EXACT_MASS>
516.126776232

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
50.156182474639834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.158230316666666

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.907578720562968

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.209402664079978

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246899366301757

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
126.76419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.358  -0.072   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.358  -1.612   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.690  -2.382   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.019  -1.612   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.019  -0.072   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.690   0.696   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.356   1.467   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.977  -2.382   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.354  -2.382   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.978   0.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.312   1.467   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.978  -0.844   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.646   0.697   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.980   1.468   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.976   3.006   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.311   3.773   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.645   3.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.648   1.463   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.314   0.698   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.982   0.693   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -8.977   3.776   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.690  -3.922   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.024  -4.692   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.023  -6.233   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.358  -3.921   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.357  -7.003   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.357  -8.544   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.023  -9.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.026 -10.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.359 -11.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.695 -10.852   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.690  -9.314   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.029 -11.622   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.357 -13.159   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.690   2.236   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.024   3.006   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.357   3.006   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7   35                                             
CONECT    7    6   10                                                       
CONECT    8    2                                                            
CONECT    9    4                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   14   18                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22    3   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   26                                                       
CONECT   25   23                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   27   31                                                       
CONECT   33   31                                                            
CONECT   34   30                                                            
CONECT   35    6   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
1,4-Di-O-caffeoylquinate	Generator
1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid	HMDB
1,4-Dicaffeoylquinic acid	HMDB
1,4-Dicaffeylquinic acid	HMDB
NSC 91529	HMDB
(1S,3R,4S,5R)-1,4-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylate	Generator

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4509 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

(1S,3R,4S,5R)-1,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid

Traditional Name

(1S,3R,4S,5R)-1,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(32)36-23-19(30)11-25(24(34)35,12-20(23)31)37-22(33)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-31H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

InChI Key

IYXQRCXQQWUFQV-PSEXTPKNSA-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
Helichrysum italicum	Plant	KNApSAcK

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
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Catechol
Styrene
Phenol
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Cyclohexanol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	2.06	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	50.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0034766

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013317

KNApSAcK ID

Not Available

Chemspider ID

22912997

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid (NP0085288)

MOL for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

3D MOL for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

3D SDF for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

3D-SDF for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

PDB for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

3D PDB for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

SMILES for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

INCHI for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

Structure for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)

3D Structure for NP0085288 (1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid)