NP-MRD: Showing NP-Card for (-)-Dracunculifoside M (NP0072865)

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Record Information

Version

2.0

Created at

2022-04-28 18:08:55 UTC

Updated at

2022-04-28 18:08:55 UTC

NP-MRD ID

NP0072865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Dracunculifoside M

Description

Dracunculifoside M belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (-)-Dracunculifoside M is found in Baccharis dracunculifolia DC. . Based on a literature review very few articles have been published on Dracunculifoside M.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220082D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282220082D          

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   -7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -1.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051   -1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933   -2.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    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
  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
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 25 30  1  0  0  0  0
  5 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
  4 34  1  1  0  0  0
 33 35  1  6  0  0  0
 33 36  1  1  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
  5 39  1  1  0  0  0
  3 40  1  1  0  0  0
  3 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0072865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]1(O)CC[C@@]2(C)[C@@H](CC[C@](C)(O)[C@@H]2C1)O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O11/c1-16(2)30(38)12-11-28(3)21(14-30)29(4,37)10-9-22(28)41-27-26(36)25(35)24(34)20(40-27)15-39-23(33)8-6-17-5-7-18(31)19(32)13-17/h5-8,13,16,20-22,24-27,31-32,34-38H,9-12,14-15H2,1-4H3/b8-6+/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+/m1/s1

> <INCHI_KEY>
HEEPALWVIOOYNB-NKIVAHPMSA-N

> <FORMULA>
C30H44O11

> <MOLECULAR_WEIGHT>
580.671

> <EXACT_MASS>
580.288362237

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
61.97920794394223

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(1R,4S,4aR,6S,8aR)-4,6-dihydroxy-4,8a-dimethyl-6-(propan-2-yl)-decahydronaphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
2.1451873259999985

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.064818500162406

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208201687996912

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9040038975513722

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
147.57040000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(1R,4S,4aR,6S,8aR)-4,6-dihydroxy-6-isopropyl-4,8a-dimethyl-hexahydro-1H-naphthalen-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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.670   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.337   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -16.004   4.620   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -16.004   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.540  -2.364   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.817  -3.616   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.356  -3.562   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.094  -4.976   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.723  -4.440   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   40   41                                             
CONECT    4    3    5   34                                                  
CONECT    5    4    6   31   39                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26                                                            
CONECT   30   25                                                            
CONECT   31    5   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33    4                                                       
CONECT   35   33                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39    5                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₁₁

Average Mass

580.6710 Da

Monoisotopic Mass

580.28836 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-{[(1R,4S,4aR,6S,8aR)-4,6-dihydroxy-4,8a-dimethyl-6-(propan-2-yl)-decahydronaphthalen-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-{[(1R,4S,4aR,6S,8aR)-4,6-dihydroxy-6-isopropyl-4,8a-dimethyl-hexahydro-1H-naphthalen-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(C)[C@]1(O)CC[C@@]2(C)[C@@H](CC[C@](C)(O)[C@@H]2C1)O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H44O11/c1-16(2)30(38)12-11-28(3)21(14-30)29(4,37)10-9-22(28)41-27-26(36)25(35)24(34)20(40-27)15-39-23(33)8-6-17-5-7-18(31)19(32)13-17/h5-8,13,16,20-22,24-27,31-32,34-38H,9-12,14-15H2,1-4H3/b8-6+/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+/m1/s1

InChI Key

HEEPALWVIOOYNB-NKIVAHPMSA-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 terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Sesquiterpenoid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
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	1.53	ALOGPS
logP	2.15	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	147.57 m³·mol⁻¹	ChemAxon
Polarizability	61.98 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

C00032926

Chemspider ID

9138134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10962920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Dracunculifoside M (NP0072865)

MOL for NP0072865 ((-)-Dracunculifoside M)

3D MOL for NP0072865 ((-)-Dracunculifoside M)

3D SDF for NP0072865 ((-)-Dracunculifoside M)

3D-SDF for NP0072865 ((-)-Dracunculifoside M)

PDB for NP0072865 ((-)-Dracunculifoside M)

3D PDB for NP0072865 ((-)-Dracunculifoside M)

SMILES for NP0072865 ((-)-Dracunculifoside M)

INCHI for NP0072865 ((-)-Dracunculifoside M)

Structure for NP0072865 ((-)-Dracunculifoside M)

3D Structure for NP0072865 ((-)-Dracunculifoside M)