NP-MRD: Showing NP-Card for (1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid (NP0212582)

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Record Information

Version

2.0

Created at

2022-09-05 11:17:20 UTC

Updated at

2022-09-05 11:17:20 UTC

NP-MRD ID

NP0212582

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid

Description

(1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid is found in Buphthalmum salicifolium.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213172D          

 42 44  0  0  1  0            999 V2000
    4.8289   -2.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -2.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  7 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052213172D          

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   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  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  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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  2  0  0  0  0
 18 25  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 34 41  1  0  0  0  0
 28 42  1  0  0  0  0
  7 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212582

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@@]1(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](C1)OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H30O13/c1-15(2)27(37)42-29(28(38)39)13-22(40-24(34)9-5-16-3-7-18(30)20(32)11-16)26(36)23(14-29)41-25(35)10-6-17-4-8-19(31)21(33)12-17/h3-12,15,22-23,26,30-33,36H,13-14H2,1-2H3,(H,38,39)/b9-5+,10-6+/t22-,23-,26-,29+/m1/s1

> <INCHI_KEY>
XNFNPKMIOPRXMH-QHNIOFFGSA-N

> <FORMULA>
C29H30O13

> <MOLECULAR_WEIGHT>
586.546

> <EXACT_MASS>
586.168641026

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
57.95804700284948

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
3.8428778523333325

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.90755978887337

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3718819248164635

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6041071971576333

> <JCHEM_POLAR_SURFACE_AREA>
217.34999999999997

> <JCHEM_REFRACTIVITY>
145.1171

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

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

> <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  C   UNK     0       9.014  -5.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.497  -4.838   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.971  -3.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.508  -6.018   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.034  -7.465   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.991  -5.750   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.011  -5.750   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.495  -6.018   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.538  -4.303   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -7.700   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  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11   42                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18                                                       
CONECT   26   12   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   42                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   34                                                       
CONECT   42   28    7                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₀O₁₃

Average Mass

586.5460 Da

Monoisotopic Mass

586.16864 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@@]1(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](C1)OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C29H30O13/c1-15(2)27(37)42-29(28(38)39)13-22(40-24(34)9-5-16-3-7-18(30)20(32)11-16)26(36)23(14-29)41-25(35)10-6-17-4-8-19(31)21(33)12-17/h3-12,15,22-23,26,30-33,36H,13-14H2,1-2H3,(H,38,39)/b9-5+,10-6+/t22-,23-,26-,29+/m1/s1

InChI Key

XNFNPKMIOPRXMH-QHNIOFFGSA-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
Buphthalmum salicifolium	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	3.84	ChemAxon
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	217.35 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	145.12 m³·mol⁻¹	ChemAxon
Polarizability	57.96 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

LOTUS database [Link]

Showing NP-Card for (1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid (NP0212582)

MOL for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

3D MOL for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

3D SDF for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

3D-SDF for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

PDB for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

3D PDB for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

SMILES for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

INCHI for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

Structure for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)

3D Structure for NP0212582 ((1s,3r,4s,5r)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-1-[(2-methylpropanoyl)oxy]cyclohexane-1-carboxylic acid)