NP-MRD: Showing NP-Card for 3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid (NP0229011)

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Record Information

Version

2.0

Created at

2022-09-06 08:53:46 UTC

Updated at

2022-09-06 08:53:46 UTC

NP-MRD ID

NP0229011

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

Description

3,4,5-Tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. 3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid is found in Terminalia chebula. 3,4,5-Tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171500182D          

 45 48  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -5.3625    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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  4 33  1  0  0  0  0
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 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 37 45  1  0  0  0  0
M  END

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004171500182D          

 45 48  0  0  0  0            999 V2000
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   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 10 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 23 31  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
  4 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 37 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229011

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(C1)OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O17/c29-13-1-10(2-14(30)21(13)35)26(40)43-19-7-9(25(38)39)8-20(44-27(41)11-3-15(31)22(36)16(32)4-11)24(19)45-28(42)12-5-17(33)23(37)18(34)6-12/h1-7,19-20,24,29-37H,8H2,(H,38,39)

> <INCHI_KEY>
KRGJABLVIDOYEE-UHFFFAOYSA-N

> <FORMULA>
C28H22O17

> <MOLECULAR_WEIGHT>
630.467

> <EXACT_MASS>
630.085699248

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
58.428705387622045

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.113737573999999

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.642283120597284

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9247991003549427

> <JCHEM_PKA_STRONGEST_BASIC>
-5.5489416091600505

> <JCHEM_POLAR_SURFACE_AREA>
298.27

> <JCHEM_REFRACTIVITY>
146.25439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10                                                       
CONECT   19    6   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23                                                       
CONECT   32   19   33   34                                                  
CONECT   33   32    4                                                       
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   45                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   37                                                       
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylate	Generator

Chemical Formula

C₂₈H₂₂O₁₇

Average Mass

630.4670 Da

Monoisotopic Mass

630.08570 Da

IUPAC Name

3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

Traditional Name

3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(C1)OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C28H22O17/c29-13-1-10(2-14(30)21(13)35)26(40)43-19-7-9(25(38)39)8-20(44-27(41)11-3-15(31)22(36)16(32)4-11)24(19)45-28(42)12-5-17(33)23(37)18(34)6-12/h1-7,19-20,24,29-37H,8H2,(H,38,39)

InChI Key

KRGJABLVIDOYEE-UHFFFAOYSA-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
Terminalia chebula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Galloyl ester
Tetracarboxylic acid or derivatives
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Benzenetriol
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclitol or derivatives
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Polyol
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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
logP	2.79	ALOGPS
logP	3.11	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.92	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	298.27 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	146.25 m³·mol⁻¹	ChemAxon
Polarizability	58.43 Å³	ChemAxon
Number of Rings	4	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

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

14653357

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid (NP0229011)

MOL for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D MOL for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D SDF for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D-SDF for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

PDB for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D PDB for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

SMILES for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

INCHI for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

Structure for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)

3D Structure for NP0229011 (3,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohex-1-ene-1-carboxylic acid)