NP-MRD: Showing NP-Card for 3,5-Dicaffeoyl-4-succinoylquinic acid (NP0084918)

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Record Information

Version

2.0

Created at

2022-04-29 05:32:03 UTC

Updated at

2022-04-29 05:32:03 UTC

NP-MRD ID

NP0084918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-Dicaffeoyl-4-succinoylquinic acid

Description

3,5-Dicaffeoyl-4-succinoylquinic acid is found in Chrysanthemum coronarium .

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207322D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292207322D          

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    0.3343   -1.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -1.0678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 14 20  2  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 26 33  1  0  0  0  0
 23 34  2  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 36 40  1  1  0  0  0
 36 41  1  0  0  0  0
 11 41  1  0  0  0  0
  9 42  2  0  0  0  0
  6 43  1  0  0  0  0
 43 44  2  0  0  0  0
  2 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084918

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H28O15/c30-17-5-1-15(11-19(17)32)3-8-24(36)42-21-13-29(41,28(39)40)14-22(27(21)44-26(38)10-7-23(34)35)43-25(37)9-4-16-2-6-18(31)20(33)12-16/h1-6,8-9,11-12,21-22,27,30-33,41H,7,10,13-14H2,(H,34,35)(H,39,40)/b8-3+,9-4+/t21-,22-,27-,29+/m1/s1

> <INCHI_KEY>
DNZQDZDGNZZGCU-WDDIIZOCSA-N

> <FORMULA>
C29H28O15

> <MOLECULAR_WEIGHT>
616.528

> <EXACT_MASS>
616.142820202

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
59.68329526647325

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.424218473999999

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.8030610426593836

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1379866944407437

> <JCHEM_PKA_STRONGEST_BASIC>
-4.025237549852071

> <JCHEM_POLAR_SURFACE_AREA>
254.64999999999995

> <JCHEM_REFRACTIVITY>
146.80899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4S,5R)-4-[(3-carboxypropanoyl)oxy]-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1-hydroxycyclohexane-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 -17.710   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667 -15.400   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003  -8.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337  -6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.141  -3.173   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.624  -2.905   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       3.131  -1.993   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.151  -4.887   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.334  -8.470   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.335 -15.400   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   44                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   43                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   42                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   41                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14                                                            
CONECT   21   12   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26                                                       
CONECT   34   23                                                            
CONECT   35   21   36                                                       
CONECT   36   35   37   40   41                                             
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   36                                                            
CONECT   41   36   11                                                       
CONECT   42    9                                                            
CONECT   43    6   44                                                       
CONECT   44   43    2                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₈O₁₅

Average Mass

616.5280 Da

Monoisotopic Mass

616.14282 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H28O15/c30-17-5-1-15(11-19(17)32)3-8-24(36)42-21-13-29(41,28(39)40)14-22(27(21)44-26(38)10-7-23(34)35)43-25(37)9-4-16-2-6-18(31)20(33)12-16/h1-6,8-9,11-12,21-22,27,30-33,41H,7,10,13-14H2,(H,34,35)(H,39,40)/b8-3+,9-4+/t21-,22-,27-,29+/m1/s1

InChI Key

DNZQDZDGNZZGCU-WDDIIZOCSA-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
Chrysanthemum coronarium	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	2.35	ALOGPS
logP	2.42	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	254.65 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	146.81 m³·mol⁻¹	ChemAxon
Polarizability	59.68 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

Not Available

References

General References

Not Available

Showing NP-Card for 3,5-Dicaffeoyl-4-succinoylquinic acid (NP0084918)

MOL for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

3D MOL for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

3D SDF for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

3D-SDF for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

PDB for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

3D PDB for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

SMILES for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

INCHI for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

Structure for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)

3D Structure for NP0084918 (3,5-Dicaffeoyl-4-succinoylquinic acid)