NP-MRD: Showing NP-Card for 1,3-Dicaffeoylquinic acid (NP0044064)

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Record Information

Version

1.0

Created at

2021-11-12 23:48:05 UTC

Updated at

2021-11-26 17:45:02 UTC

NP-MRD ID

NP0044064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3-Dicaffeoylquinic acid

Description

1,3-Dicaffeoylquinic acid, also known as cinarin or 15-O-trans-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. 1,3-Dicaffeoylquinic acid is found in Arctium lappa, Arnica chamissonis, Aster indicus, Cynara cardunculus , Cynara scolymus , Isertia pittieri, Mikania hirsutissima and Xanthium strumarium. It was first documented in 2006 (PMID: 17090114). 1,3-Dicaffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 20428313).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100482D          

 37 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652311132100482D          

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M  END
> <DATABASE_ID>
NP0044064

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@@](C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O)(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(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

> <INCHI_KEY>
YDDUMTOHNYZQPO-PSEXTPKNSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.4509

> <EXACT_MASS>
516.126776232

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.622612335951445

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.158230316666666

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.907564069574317

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.184533116763618

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2325629248174694

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
126.76419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0      -6.552  -2.972   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -7.885  -3.742   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.885  -5.282   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.552  -6.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.552  -7.592   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.218  -8.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.218  -9.902   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.552 -10.672   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.552 -12.212   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.885  -9.902   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -9.219 -10.672   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -7.885  -8.362   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -9.219  -2.972   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -9.219  -1.432   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.553  -0.662   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.553   0.878   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -12.069   0.611   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -12.596  -0.837   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -11.606  -2.016   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -14.113  -1.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.639  -2.551   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -16.156  -2.819   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -16.683  -4.266   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -18.199  -4.533   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -19.189  -3.353   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -20.706  -3.621   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -18.662  -1.906   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -19.652  -0.727   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -17.146  -1.639   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -11.079   2.325   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -10.090   3.505   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -12.596   2.593   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -9.219   1.648   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.885   0.878   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.552   1.648   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.885  -0.662   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.552  -1.432   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                                                       
CONECT   16   15   17   30   33                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22                                                       
CONECT   30   16   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   16   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   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
1,3-Dicaffeoylquinate	Generator
15-O-trans-Dicaffeoylquinic acid	HMDB
15-O-trans-Dicaffeoylquinate	HMDB
1,3-Di-O-caffeoylquinic acid	HMDB
1,5-Dicaffeoylquinic acid?	HMDB
Cinarin	HMDB
Listrocol	HMDB
Cynarex	HMDB
Cinarine	HMDB
Nivellipid	HMDB
Phemocil	HMDB
1,5-Dicaffeoylquinic acid	HMDB
1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)	HMDB
Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer	HMDB
Listricol	HMDB
Cinarina	HMDB
Cynarin	HMDB
Cynarine	HMDB
Cynarix	HMDB
(1S,3R,4R,5R)-1,3-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylate	Generator
1,3-Dicaffeoylquinic acid	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4509 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@](C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O)(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(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

InChI Key

YDDUMTOHNYZQPO-PSEXTPKNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arctium lappa	LOTUS Database	35616633
Arnica chamissonis	LOTUS Database	35616633
Aster indicus	LOTUS Database	35616633
Cynara cardunculus	Plant	KNApSAcK
Cynara scolymus	Plant	KNApSAcK
Isertia pittieri	LOTUS Database	35616633
Mikania hirsutissima	LOTUS Database	35616633
Xanthium strumarium	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 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
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
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	2.07	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.18	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	49.62 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

HMDB0029279

DrugBank ID

Not Available

Phenol Explorer Compound ID

526

FoodDB ID

FDB000278

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

6474640

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
Dini I, Tenore GC, Dini A: New polyphenol derivative in Ipomoea batatas tubers and its antioxidant activity. J Agric Food Chem. 2006 Nov 15;54(23):8733-7. doi: 10.1021/jf061687v. [PubMed:17090114 ]

Showing NP-Card for 1,3-Dicaffeoylquinic acid (NP0044064)

MOL for NP0044064 (1,3-Dicaffeoylquinic acid)

3D MOL for NP0044064 (1,3-Dicaffeoylquinic acid)

3D SDF for NP0044064 (1,3-Dicaffeoylquinic acid)

3D-SDF for NP0044064 (1,3-Dicaffeoylquinic acid)

PDB for NP0044064 (1,3-Dicaffeoylquinic acid)

3D PDB for NP0044064 (1,3-Dicaffeoylquinic acid)

SMILES for NP0044064 (1,3-Dicaffeoylquinic acid)

INCHI for NP0044064 (1,3-Dicaffeoylquinic acid)

Structure for NP0044064 (1,3-Dicaffeoylquinic acid)

3D Structure for NP0044064 (1,3-Dicaffeoylquinic acid)