NP-MRD: Showing NP-Card for (-)-Dracunculifoside L (NP0072864)

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Record Information

Version

2.0

Created at

2022-04-28 18:08:33 UTC

Updated at

2022-04-28 18:08:33 UTC

NP-MRD ID

NP0072864

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Dracunculifoside L

Description

[(2R,3S,4S,5R,6R)-6-({2-[(2R,3S)-6-acetyl-3,5-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-en-1-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (-)-Dracunculifoside L is found in Baccharis dracunculifolia DC. . Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6R)-6-({2-[(2R,3S)-6-acetyl-3,5-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-en-1-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220082D          

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M  END

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  Mrv1652304282220082D          

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   -7.6409   -5.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0534   -4.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6409   -4.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8784   -4.9848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0534   -6.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409   -4.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -4.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -2.8414    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 13 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
  4 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  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
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 35 37  1  0  0  0  0
 34 38  1  0  0  0  0
  3 39  1  6  0  0  0
  2 40  1  1  0  0  0
  1 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0072864

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=CC2=C(C=C1O)[C@H](O)[C@H](O2)C(=C)CO[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O13/c1-12(27-23(34)16-8-18(31)15(13(2)29)9-20(16)40-27)10-39-28-26(37)25(36)24(35)21(41-28)11-38-22(33)6-4-14-3-5-17(30)19(32)7-14/h3-9,21,23-28,30-32,34-37H,1,10-11H2,2H3/b6-4+/t21-,23+,24-,25+,26-,27-,28-/m1/s1

> <INCHI_KEY>
VTMMVIHOOIWLKC-KNVZQHPBSA-N

> <FORMULA>
C28H30O13

> <MOLECULAR_WEIGHT>
574.535

> <EXACT_MASS>
574.168641026

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.705959705669414

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-({2-[(2R,3S)-6-acetyl-3,5-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-en-1-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
1.2500805439999993

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.585768204758603

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.972855784255483

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490924951140364

> <JCHEM_POLAR_SURFACE_AREA>
212.66999999999996

> <JCHEM_REFRACTIVITY>
140.25440000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-({2-[(2R,3S)-6-acetyl-3,5-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-en-1-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.023  -5.304   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.793  -6.638   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.333  -6.638   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.103  -5.304   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.333  -3.970   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.793  -3.970   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.023  -2.637   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.268  -2.549   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.744   1.408   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.531  -2.073   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -9.643  -5.304   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -10.413  -3.970   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -11.953  -3.970   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -12.723  -2.637   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -12.723  -5.304   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -11.953  -6.638   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.723  -7.971   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -11.953  -9.305   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -12.723 -10.639   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -14.263 -10.639   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -15.033  -9.305   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -14.263  -7.971   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -16.573  -9.305   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -15.033 -11.972   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -8.103  -7.971   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -5.023  -7.971   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -3.483  -5.304   0.000  0.00  0.00           O+0
CONECT    1    2    6   41                                                  
CONECT    2    1    3   40                                                  
CONECT    3    2    4   39                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   11   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   13                                                       
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18                                                            
CONECT   25    4   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   38                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   31                                                       
CONECT   37   35                                                            
CONECT   38   34                                                            
CONECT   39    3                                                            
CONECT   40    2                                                            
CONECT   41    1                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6R)-6-({2-[(2R,3S)-6-acetyl-3,5-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-en-1-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₈H₃₀O₁₃

Average Mass

574.5350 Da

Monoisotopic Mass

574.16864 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-({2-[(2R,3S)-6-acetyl-3,5-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-en-1-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6R)-6-({2-[(2R,3S)-6-acetyl-3,5-dihydroxy-2,3-dihydro-1-benzofuran-2-yl]prop-2-en-1-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)C1=CC2=C(C=C1O)[C@H](O)[C@H](O2)C(=C)CO[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C28H30O13/c1-12(27-23(34)16-8-18(31)15(13(2)29)9-20(16)40-27)10-39-28-26(37)25(36)24(35)21(41-28)11-38-22(33)6-4-14-3-5-17(30)19(32)7-14/h3-9,21,23-28,30-32,34-37H,1,10-11H2,2H3/b6-4+/t21-,23+,24-,25+,26-,27-,28-/m1/s1

InChI Key

VTMMVIHOOIWLKC-KNVZQHPBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Baccharis dracunculifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Acetophenone
Coumaran
Catechol
Styrene
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Ether
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.36	ALOGPS
logP	1.25	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.97	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	140.25 m³·mol⁻¹	ChemAxon
Polarizability	56.71 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

162976634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Dracunculifoside L (NP0072864)

MOL for NP0072864 ((-)-Dracunculifoside L)

3D MOL for NP0072864 ((-)-Dracunculifoside L)

3D SDF for NP0072864 ((-)-Dracunculifoside L)

3D-SDF for NP0072864 ((-)-Dracunculifoside L)

PDB for NP0072864 ((-)-Dracunculifoside L)

3D PDB for NP0072864 ((-)-Dracunculifoside L)

SMILES for NP0072864 ((-)-Dracunculifoside L)

INCHI for NP0072864 ((-)-Dracunculifoside L)

Structure for NP0072864 ((-)-Dracunculifoside L)

3D Structure for NP0072864 ((-)-Dracunculifoside L)