NP-MRD: Showing NP-Card for 3-Caffeoyl-4-feruloylquinic acid (NP0085393)

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Record Information

Version

2.0

Created at

2022-04-29 05:56:14 UTC

Updated at

2022-04-29 05:56:14 UTC

NP-MRD ID

NP0085393

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Caffeoyl-4-feruloylquinic acid

Description

4-Feruloyl-5-caffeoylquinic 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. 3-Caffeoyl-4-feruloylquinic acid is found in Citrus reticulata . 3-Caffeoyl-4-feruloylquinic acid was first documented in 2019 (PMID: 31713022). Based on a literature review very few articles have been published on 4-Feruloyl-5-caffeoylquinic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207562D          

 38 40  0  0  1  0            999 V2000
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    0.0000   -1.6500    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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  2 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292207562D          

 38 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0085393

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2[C@H](O)C[C@](O)(C[C@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O12/c1-36-20-11-15(3-7-17(20)28)5-9-23(32)38-24-19(30)12-26(35,25(33)34)13-21(24)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h2-11,19,21,24,27-30,35H,12-13H2,1H3,(H,33,34)/b8-4+,9-5+/t19-,21-,24-,26+/m1/s1

> <INCHI_KEY>
RKAYMOSEFYVEJU-DRFAHUGVSA-N

> <FORMULA>
C26H26O12

> <MOLECULAR_WEIGHT>
530.482

> <EXACT_MASS>
530.142426277

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.95975406802272

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.3041243726666663

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.122514544688554

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.310916931495464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246879196378373

> <JCHEM_POLAR_SURFACE_AREA>
200.28

> <JCHEM_REFRACTIVITY>
131.24649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.49e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334 -11.550   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      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.011 -15.810   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.991 -15.810   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.508 -15.542   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.464 -17.257   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   36                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   34                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18                                                       
CONECT   26   15                                                            
CONECT   27   13   28                                                       
CONECT   28   27   29   30   33                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34                                                       
CONECT   34   33   12   35                                                  
CONECT   35   34                                                            
CONECT   36   10                                                            
CONECT   37    7   38                                                       
CONECT   38   37    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
4-Feruloyl-5-caffeoylquinate	Generator

Chemical Formula

C₂₆H₂₆O₁₂

Average Mass

530.4820 Da

Monoisotopic Mass

530.14243 Da

IUPAC Name

(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Traditional Name

(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2[C@H](O)C[C@](O)(C[C@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)=O)=C1

InChI Identifier

InChI=1S/C26H26O12/c1-36-20-11-15(3-7-17(20)28)5-9-23(32)38-24-19(30)12-26(35,25(33)34)13-21(24)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h2-11,19,21,24,27-30,35H,12-13H2,1H3,(H,33,34)/b8-4+,9-5+/t19-,21-,24-,26+/m1/s1

InChI Key

RKAYMOSEFYVEJU-DRFAHUGVSA-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
Citrus reticulata	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
Methoxyphenol
Tricarboxylic acid or derivatives
Anisole
Catechol
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Hydroxy acid
Fatty acyl
Benzenoid
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	2.55	ALOGPS
logP	2.3	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	131.25 m³·mol⁻¹	ChemAxon
Polarizability	51.96 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055232

Chemspider ID

8112448

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9936820

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Torres A, Basurto F, Navarro-Ocana A: Quantitative Analysis of the Biologically Active Compounds Present in Leaves of Mexican Sweet Potato Accessions: Phenols, Flavonoids, Anthocyanins, 3,4,5-Tri-Caffeoylquinic Acid and 4-Feruloyl-5-Caffeoylquinic Acid. Plant Foods Hum Nutr. 2019 Dec;74(4):531-537. doi: 10.1007/s11130-019-00774-2. [PubMed:31713022 ]

Showing NP-Card for 3-Caffeoyl-4-feruloylquinic acid (NP0085393)

MOL for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

3D MOL for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

3D SDF for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

3D-SDF for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

PDB for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

3D PDB for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

SMILES for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

INCHI for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

Structure for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)

3D Structure for NP0085393 (3-Caffeoyl-4-feruloylquinic acid)