NP-MRD: Showing NP-Card for (-)-Scorzonerin (NP0073712)

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Record Information

Version

2.0

Created at

2022-04-28 18:56:06 UTC

Updated at

2022-04-28 18:56:07 UTC

NP-MRD ID

NP0073712

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Scorzonerin

Description

(3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propanoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (-)-Scorzonerin is found in Scorzonera pseudodivaricata and Scozonera pseudodivaricata Lipsch.. Based on a literature review very few articles have been published on (3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220562D          

 41 45  0  0  1  0            999 V2000
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282220562D          

 41 45  0  0  1  0            999 V2000
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   -1.1140   -6.4041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8820   -6.1027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0050   -5.2870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3599   -4.7726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5920   -5.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4829   -3.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2509   -3.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7729   -4.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5270   -6.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911   -7.2199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  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  1  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
  5 13  1  6  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  1  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
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  1  0  0  0
 31 32  1  0  0  0  0
 28 33  1  6  0  0  0
 27 34  1  1  0  0  0
 26 35  1  6  0  0  0
  3 36  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
  1 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073712

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](OC1=O)[C@H]1C(C)=CC(=O)C1=C(C)C[C@@H]2OC(=O)CCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O11/c1-13-10-18(32)22-14(2)11-19(24-15(3)29(37)41-28(24)23(13)22)39-21(33)9-6-16-4-7-17(8-5-16)38-30-27(36)26(35)25(34)20(12-31)40-30/h4-5,7-8,10,15,19-20,23-28,30-31,34-36H,6,9,11-12H2,1-3H3/t15-,19-,20+,23-,24+,25+,26-,27+,28+,30+/m0/s1

> <INCHI_KEY>
BYXHHIFURZUBKJ-JHTHEGFKSA-N

> <FORMULA>
C30H36O11

> <MOLECULAR_WEIGHT>
572.607

> <EXACT_MASS>
572.225761979

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
59.3231399377186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propanoate

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.269775812666667

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19026066530083

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199482242867262

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686494

> <JCHEM_POLAR_SURFACE_AREA>
169.04999999999998

> <JCHEM_REFRACTIVITY>
142.8867

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propanoate

> <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       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.455   0.843   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.766   1.393   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.616  -1.954   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.482  -4.108   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.711  -5.631   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.507  -6.591   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.145  -6.193   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.374  -7.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.170  -8.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.400 -10.199   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.196 -11.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.762 -10.597   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.533  -9.074   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.737  -8.114   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.558 -11.557   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.876 -10.994   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.080 -11.954   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.513 -11.392   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.743  -9.869   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.539  -8.909   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.105  -9.471   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.768  -7.386   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.202  -6.823   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.176  -9.306   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.717 -12.352   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.850 -13.477   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.665  -4.108   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.530  -1.954   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.176   0.433   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.691   0.843   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.150   2.285   0.000  0.00  0.00           C+0
CONECT    1    2    7   40                                                  
CONECT    2    1    3   37                                                  
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6   12                                                  
CONECT   12   11                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   35                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28                                                            
CONECT   34   27                                                            
CONECT   35   26                                                            
CONECT   36    3                                                            
CONECT   37    2   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39    1   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
(3S,3AR,4S,9as,9BR)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propanoic acid	Generator

Chemical Formula

C₃₀H₃₆O₁₁

Average Mass

572.6070 Da

Monoisotopic Mass

572.22576 Da

IUPAC Name

(3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propanoate

Traditional Name

(3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propanoate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](OC1=O)[C@H]1C(C)=CC(=O)C1=C(C)C[C@@H]2OC(=O)CCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

InChI Identifier

InChI=1S/C30H36O11/c1-13-10-18(32)22-14(2)11-19(24-15(3)29(37)41-28(24)23(13)22)39-21(33)9-6-16-4-7-17(8-5-16)38-30-27(36)26(35)25(34)20(12-31)40-30/h4-5,7-8,10,15,19-20,23-28,30-31,34-36H,6,9,11-12H2,1-3H3/t15-,19-,20+,23-,24+,25+,26-,27+,28+,30+/m0/s1

InChI Key

BYXHHIFURZUBKJ-JHTHEGFKSA-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
Scorzonera pseudodivaricata	LOTUS Database	35616633
Scozonera pseudodivaricata Lipsch.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Phenol ether
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Fatty acyl
Benzenoid
Tetrahydrofuran
Lactone
Ketone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Primary 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	1.02	ALOGPS
logP	1.27	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	142.89 m³·mol⁻¹	ChemAxon
Polarizability	59.32 Å³	ChemAxon
Number of Rings	5	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

20567701

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16736245

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Scorzonerin (NP0073712)

MOL for NP0073712 ((-)-Scorzonerin)

3D MOL for NP0073712 ((-)-Scorzonerin)

3D SDF for NP0073712 ((-)-Scorzonerin)

3D-SDF for NP0073712 ((-)-Scorzonerin)

PDB for NP0073712 ((-)-Scorzonerin)

3D PDB for NP0073712 ((-)-Scorzonerin)

SMILES for NP0073712 ((-)-Scorzonerin)

INCHI for NP0073712 ((-)-Scorzonerin)

Structure for NP0073712 ((-)-Scorzonerin)

3D Structure for NP0073712 ((-)-Scorzonerin)