NP-MRD: Showing NP-Card for (3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid (NP0244141)

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Record Information

Version

2.0

Created at

2022-09-07 04:51:18 UTC

Updated at

2022-09-07 04:51:18 UTC

NP-MRD ID

NP0244141

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

1,4-Dicaffeoylquinic acid 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. (3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid is found in Helichrysum stoechas, Pyrus communis, Sanicula graveolens and Urospermum dalechampii. Based on a literature review very few articles have been published on 1,4-Dicaffeoylquinic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206512D          

 37 39  0  0  1  0            999 V2000
   -0.4741   -5.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -6.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -6.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741   -7.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741   -8.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404   -8.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404   -9.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741   -9.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741  -10.7049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -9.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -9.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -8.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -5.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -4.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175   -4.5174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3319   -4.9299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7761   -2.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4741   -4.9299    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
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 14 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END

     RDKit          3D

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   -6.4991    1.1661    1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3235   -1.1303   -0.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612   -1.3920   -1.0025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9220   -0.8273   -2.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3410   -1.8306   -3.2785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -0.5298   -2.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    0.5938   -1.8591 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.4091    0.2902   -2.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0201   -0.7513   -0.1084 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -8.9421   -1.4046    2.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309072206512D          

 37 39  0  0  1  0            999 V2000
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 18 35  1  0  0  0  0
 35 36  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0244141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC(C[C@@H](O)C1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O

> <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-RDJMKVHDSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.455

> <EXACT_MASS>
516.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.13984414736679

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.158230316666666

> <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>
126.76419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,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                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.885 -10.743   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.219 -11.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.219 -13.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.885 -13.823   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.885 -15.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.449 -16.133   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.449 -17.673   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.885 -18.443   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.885 -19.983   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.219 -17.673   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.552 -18.443   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.219 -16.133   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.552 -10.743   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.552  -9.203   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.886  -8.433   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.220  -9.203   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.886  -6.893   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.552  -6.123   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.542  -4.943   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.059  -5.210   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.585  -6.657   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.049  -4.031   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.565  -4.298   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.555  -3.118   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.072  -3.386   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.062  -2.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -11.535  -0.759   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -12.525   0.421   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -10.018  -0.491   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -9.492   0.956   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.028  -1.671   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.562  -4.943   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.046  -5.210   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.089  -3.496   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.219  -6.893   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.219  -8.433   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.885  -9.203   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   36                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   32   35                                             
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                                                       
CONECT   32   18   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   18   36                                                       
CONECT   36   35   14   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
1,4-Dicaffeoylquinate	Generator
1,4-Di-O-caffeoylquinic acid	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4550 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC(C[C@@H](O)C1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O

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-RDJMKVHDSA-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
Helichrysum stoechas	LOTUS Database	35616633
Pyrus communis	LOTUS Database	35616633
Sanicula graveolens	LOTUS Database	35616633
Urospermum dalechampii	LOTUS Database	35616633

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

65793557

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12358846

PDB ID

Not Available

ChEBI ID

176204

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid (NP0244141)

MOL for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

3D MOL for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

3D SDF for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

3D-SDF for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

PDB for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

3D PDB for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

SMILES for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

INCHI for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

Structure for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)

3D Structure for NP0244141 ((3r,5r)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid)