NP-MRD: Showing NP-Card for 15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A (NP0074890)

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Record Information

Version

2.0

Created at

2022-04-28 20:12:13 UTC

Updated at

2022-04-28 20:12:13 UTC

NP-MRD ID

NP0074890

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A

Description

[(2R,3S,4S,5R,6R)-6-{[(3aR,4S,11aS)-6-formyl-4-hydroxy-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. 15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A is found in Sonchus asper . Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6R)-6-{[(3aR,4S,11aS)-6-formyl-4-hydroxy-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222122D          

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M  END

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M  END


  Mrv1652304282222122D          

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    5.8959   11.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1872   10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7905   11.9798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3233    2.0275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -0.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 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
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 17 20  1  6  0  0  0
 16 21  1  1  0  0  0
 15 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 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
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
  7 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  6 37  1  1  0  0  0
 37 38  2  0  0  0  0
  5 39  1  1  0  0  0
  3 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0074890

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)CC2=CC=C(O)C=C2)O[C@@H](OC\C2=C\[C@@H]3OC(=O)C(=C)[C@@H]3[C@@H](O)C\C(C=O)=C/CC2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O12/c1-15-24-20(32)9-17(12-30)3-2-4-18(10-21(24)40-28(15)37)13-39-29-27(36)26(35)25(34)22(41-29)14-38-23(33)11-16-5-7-19(31)8-6-16/h3,5-8,10,12,20-22,24-27,29,31-32,34-36H,1-2,4,9,11,13-14H2/b17-3+,18-10+/t20-,21-,22+,24+,25+,26-,27+,29+/m0/s1

> <INCHI_KEY>
NGDUYKZDYOOZLX-LNFGRTJASA-N

> <FORMULA>
C29H34O12

> <MOLECULAR_WEIGHT>
574.579

> <EXACT_MASS>
574.205026535

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
57.88552946690158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3aR,4S,11aS)-6-formyl-4-hydroxy-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.4243742993333335

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.211413256748877

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.495586095173639

> <JCHEM_PKA_STRONGEST_BASIC>
-2.936001258598795

> <JCHEM_POLAR_SURFACE_AREA>
189.28

> <JCHEM_REFRACTIVITY>
142.3512

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3aR,4S,11aS)-6-formyl-4-hydroxy-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (4-hydroxyphenyl)acetate

> <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      10.476   3.189   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.020   1.748   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.044   0.557   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.525   0.806   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.981   2.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.461   2.497   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.917   3.937   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.893   5.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.413   4.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.957   3.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.389   6.071   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.845   7.511   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.821   8.703   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.277  10.144   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.253  11.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.773  11.085   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.317   9.645   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.341   8.453   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.884   7.012   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.836   9.395   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.749  12.277   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.709  12.776   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.685  13.967   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.141  15.408   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.622  15.657   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.117  16.599   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.574  18.040   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.054  18.289   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.510  19.730   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.486  20.922   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.006  20.672   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.549  19.231   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.942  22.362   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.379   3.866   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.972   2.380   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.531   1.836   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.259   1.534   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.331  -0.004   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.070   3.785   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      10.588  -0.884   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      12.108  -1.133   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   40                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   39                                                  
CONECT    6    5    7   37                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    1                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21   16                                                            
CONECT   22   15   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30                                                            
CONECT   34    7   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    6   38                                                  
CONECT   38   37                                                            
CONECT   39    5                                                            
CONECT   40    3   41                                                       
CONECT   41   40                                                            
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-{[(3ar,4S,11as)-6-formyl-4-hydroxy-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-10-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetic acid	Generator

Chemical Formula

C₂₉H₃₄O₁₂

Average Mass

574.5790 Da

Monoisotopic Mass

574.20503 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-{[(3aR,4S,11aS)-6-formyl-4-hydroxy-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Traditional Name

[(2R,3S,4S,5R,6R)-6-{[(3aR,4S,11aS)-6-formyl-4-hydroxy-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (4-hydroxyphenyl)acetate

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)CC2=CC=C(O)C=C2)O[C@@H](OC\C2=C\[C@@H]3OC(=O)C(=C)[C@@H]3[C@@H](O)C\C(C=O)=C/CC2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C29H34O12/c1-15-24-20(32)9-17(12-30)3-2-4-18(10-21(24)40-28(15)37)13-39-29-27(36)26(35)25(34)22(41-29)14-38-23(33)11-16-5-7-19(31)8-6-16/h3,5-8,10,12,20-22,24-27,29,31-32,34-36H,1-2,4,9,11,13-14H2/b17-3+,18-10+/t20-,21-,22+,24+,25+,26-,27+,29+/m0/s1

InChI Key

NGDUYKZDYOOZLX-LNFGRTJASA-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
Sonchus asper	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Terpene glycoside
Germacranolide
Sesquiterpenoid
Germacrane sesquiterpenoid
O-glycosyl compound
Glycosyl compound
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	0.9	ALOGPS
logP	0.42	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	142.35 m³·mol⁻¹	ChemAxon
Polarizability	57.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

162876633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A (NP0074890)

MOL for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

3D MOL for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

3D SDF for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

3D-SDF for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

PDB for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

3D PDB for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

SMILES for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

INCHI for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

Structure for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)

3D Structure for NP0074890 (15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurospermal A)