NP-MRD: Showing NP-Card for (1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid (NP0281087)

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Record Information

Version

2.0

Created at

2022-09-09 07:13:36 UTC

Updated at

2022-09-09 07:13:36 UTC

NP-MRD ID

NP0281087

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Description

(1R,3R,4S,5S)-3,4-dihydroxy-1-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic 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. (1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid is found in Urochloa ruziziensis. Based on a literature review very few articles have been published on (1R,3R,4S,5S)-3,4-dihydroxy-1-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092209132D          

 37 39  0  0  1  0            999 V2000
    3.6404   -4.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092209132D          

 37 39  0  0  1  0            999 V2000
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 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 11 33  1  0  0  0  0
  5 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281087

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O[C@@]2(C[C@@H](O)[C@H](O)[C@H](C2)OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O11/c1-35-20-12-16(4-9-18(20)28)6-11-23(31)37-26(25(33)34)13-19(29)24(32)21(14-26)36-22(30)10-5-15-2-7-17(27)8-3-15/h2-12,19,21,24,27-29,32H,13-14H2,1H3,(H,33,34)/b10-5+,11-6+/t19-,21+,24+,26-/m1/s1

> <INCHI_KEY>
YLKBTONOZYPFLU-WOCNSCFESA-N

> <FORMULA>
C26H26O11

> <MOLECULAR_WEIGHT>
514.483

> <EXACT_MASS>
514.147511657

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.57248788915406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.6076896943333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.271601293075147

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1960104416767994

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2325629248174694

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
129.2656

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.795  -8.918   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.129  -9.688   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.129 -11.228   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.463 -11.998   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.463 -13.538   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.796 -14.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.796 -15.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.130 -16.618   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.464 -15.848   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      12.130 -18.158   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.464 -18.928   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.474 -20.108   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.001 -21.555   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.957 -19.840   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.991 -17.481   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.507 -17.213   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.034 -15.766   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      17.550 -15.499   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.077 -14.052   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.540 -16.679   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.057 -16.411   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.047 -17.591   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.563 -17.323   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.553 -18.503   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.027 -19.950   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      24.017 -21.130   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      21.510 -20.218   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.520 -19.038   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.497 -18.393   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      18.014 -18.126   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      15.970 -19.840   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.960 -21.020   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.454 -20.108   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.129 -14.308   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.795 -13.538   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.795 -11.998   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.462 -11.228   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15   33                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29   16   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   11                                                       
CONECT   34    5   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
(1R,3R,4S,5S)-3,4-Dihydroxy-1-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate	Generator

Chemical Formula

C₂₆H₂₆O₁₁

Average Mass

514.4830 Da

Monoisotopic Mass

514.14751 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O[C@@]2(C[C@@H](O)[C@H](O)[C@H](C2)OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C26H26O11/c1-35-20-12-16(4-9-18(20)28)6-11-23(31)37-26(25(33)34)13-19(29)24(32)21(14-26)36-22(30)10-5-15-2-7-17(27)8-3-15/h2-12,19,21,24,27-29,32H,13-14H2,1H3,(H,33,34)/b10-5+,11-6+/t19-,21+,24+,26-/m1/s1

InChI Key

YLKBTONOZYPFLU-WOCNSCFESA-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
Urochloa ruziziensis	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
Coumaric acid ester
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Cinnamic acid or derivatives
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Styrene
Fatty acid ester
Phenol
Cyclohexanol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
1,2-diol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Ether
Organic oxide
Carbonyl group
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

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

163186034

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid (NP0281087)

MOL for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D MOL for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D SDF for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D-SDF for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

PDB for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D PDB for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

SMILES for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

INCHI for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

Structure for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D Structure for NP0281087 ((1r,3r,4s,5s)-3,4-dihydroxy-1-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)