NP-MRD: Showing NP-Card for 3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one (NP0206563)

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Record Information

Version

2.0

Created at

2022-09-05 02:51:05 UTC

Updated at

2022-09-05 02:51:05 UTC

NP-MRD ID

NP0206563

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one

Description

3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one is found in Carthamus tinctorius.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204512D          

 43 46  0  0  0  0            999 V2000
   -3.0997    4.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 12 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052204512D          

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   -6.7701    4.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2398    3.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7095    2.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9916    2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4613    1.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7435    0.5963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8041    1.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0863    1.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3344    2.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1469    2.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0522    3.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5825    3.8995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2431    3.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2431    2.9485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  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
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 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  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  0  0  0  0
 29 42  1  0  0  0  0
 12 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0206563

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(C(O)C(O)C1O)C1=C(O)C(O)(C2OC(CO)C(O)C(O)C2O)C(=O)C(C(=O)C=CC2=CC=C(O)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O16/c28-7-12-16(32)19(35)21(37)23(42-12)15-18(34)14(11(31)6-3-9-1-4-10(30)5-2-9)24(39)27(41,25(15)40)26-22(38)20(36)17(33)13(8-29)43-26/h1-6,12-13,16-17,19-23,26,28-30,32-38,40-41H,7-8H2

> <INCHI_KEY>
ZZMASNSDVDSYKO-UHFFFAOYSA-N

> <FORMULA>
C27H32O16

> <MOLECULAR_WEIGHT>
612.537

> <EXACT_MASS>
612.16903495

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
58.24628060905725

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one

> <JCHEM_LOGP>
-4.591517138333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.790636416233357

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.096647654809112

> <JCHEM_PKA_STRONGEST_BASIC>
-3.646794443393917

> <JCHEM_POLAR_SURFACE_AREA>
295.35999999999996

> <JCHEM_REFRACTIVITY>
142.52110000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0      -5.786   7.814   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -7.120   7.044   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.120   5.504   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.786   4.734   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.786   3.194   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.452   2.424   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.452   0.884   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.786   0.114   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.786  -1.426   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.120   0.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.120   2.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.454   7.814   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.454   9.354   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -7.120  10.124   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.787  10.124   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.787  11.664   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -11.121  12.434   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -11.121  13.974   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.455  14.744   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -13.788  13.974   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.787  14.744   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -9.787  16.284   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -8.454  13.974   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -7.120  14.744   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -8.454  12.434   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -7.120  11.664   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -11.121   9.354   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -12.455  10.124   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -11.121   7.814   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -12.637   8.081   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -11.648   6.367   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -10.658   5.187   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -11.184   3.740   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.195   2.560   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -10.721   1.113   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -12.701   3.473   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -13.228   2.025   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0     -13.691   4.652   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0     -15.208   4.385   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0     -13.164   6.099   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -14.154   7.279   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -9.787   7.044   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -9.787   5.504   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13   42                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   27                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   15   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   42                                             
CONECT   30   29                                                            
CONECT   31   29   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   31   41                                                  
CONECT   41   40                                                            
CONECT   42   29   12   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₆

Average Mass

612.5370 Da

Monoisotopic Mass

612.16903 Da

IUPAC Name

3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one

Traditional Name

3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

OCC1OC(C(O)C(O)C1O)C1=C(O)C(O)(C2OC(CO)C(O)C(O)C2O)C(=O)C(C(=O)C=CC2=CC=C(O)C=C2)=C1O

InChI Identifier

InChI=1S/C27H32O16/c28-7-12-16(32)19(35)21(37)23(42-12)15-18(34)14(11(31)6-3-9-1-4-10(30)5-2-9)24(39)27(41,25(15)40)26-22(38)20(36)17(33)13(8-29)43-26/h1-6,12-13,16-17,19-23,26,28-30,32-38,40-41H,7-8H2

InChI Key

ZZMASNSDVDSYKO-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
Carthamus tinctorius	LOTUS Database	35616633

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	-4.6	ChemAxon
pKa (Strongest Acidic)	3.1	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	295.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.52 m³·mol⁻¹	ChemAxon
Polarizability	58.25 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one (NP0206563)

MOL for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

3D MOL for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

3D SDF for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

3D-SDF for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

PDB for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

3D PDB for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

SMILES for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

INCHI for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

Structure for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)

3D Structure for NP0206563 (3,5,6-trihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,4-dien-1-one)