NP-MRD: Showing NP-Card for 6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid (NP0300432)

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Record Information

Version

2.0

Created at

2022-09-10 12:49:30 UTC

Updated at

2022-09-10 12:49:31 UTC

NP-MRD ID

NP0300432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid

Description

6-{3-[1-Carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid is found in Salvia yunnanensis. Based on a literature review very few articles have been published on 6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102214492D          

 41 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102214492D          

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  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
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 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
 20 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 31 38  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(CC1=CC=C(O)C(O)=C1)OC(=O)C=CC1=CC(C(C(C1C(O)=O)C(O)=O)C1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O14/c28-15-4-1-11(7-17(15)30)8-19(25(35)36)41-20(32)6-3-12-9-14(24(33)34)21(13-2-5-16(29)18(31)10-13)23(27(39)40)22(12)26(37)38/h1-7,9-10,14,19,21-23,28-31H,8H2,(H,33,34)(H,35,36)(H,37,38)(H,39,40)

> <INCHI_KEY>
JSOPGXFFNOKRAX-UHFFFAOYSA-N

> <FORMULA>
C27H24O14

> <MOLECULAR_WEIGHT>
572.475

> <EXACT_MASS>
572.116605453

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
53.75183010821826

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid

> <JCHEM_LOGP>
2.0726672896666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.5984559392628714

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.031132875442103

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2891616673888295

> <JCHEM_POLAR_SURFACE_AREA>
256.41999999999996

> <JCHEM_REFRACTIVITY>
136.21880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.000 -10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -13.090   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335 -10.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335 -10.780   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.001 -13.090   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   11   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20    5   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    2   29                                                       
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   31                                                       
CONECT   39   29   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Value	Source
6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylate	Generator

Chemical Formula

C₂₇H₂₄O₁₄

Average Mass

572.4750 Da

Monoisotopic Mass

572.11661 Da

IUPAC Name

6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid

Traditional Name

6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(CC1=CC=C(O)C(O)=C1)OC(=O)C=CC1=CC(C(C(C1C(O)=O)C(O)=O)C1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C27H24O14/c28-15-4-1-11(7-17(15)30)8-19(25(35)36)41-20(32)6-3-12-9-14(24(33)34)21(13-2-5-16(29)18(31)10-13)23(27(39)40)22(12)26(37)38/h1-7,9-10,14,19,21-23,28-31H,8H2,(H,33,34)(H,35,36)(H,37,38)(H,39,40)

InChI Key

JSOPGXFFNOKRAX-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
Salvia Yunnanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
3-phenylpropanoic-acid
Catechol
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
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	ChemAxon
pKa (Strongest Acidic)	3.03	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	256.42 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	136.22 m³·mol⁻¹	ChemAxon
Polarizability	53.75 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

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

85174254

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid (NP0300432)

MOL for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

3D MOL for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

3D SDF for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

3D-SDF for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

PDB for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

3D PDB for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

SMILES for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

INCHI for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

Structure for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)

3D Structure for NP0300432 (6-{3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl}-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid)