NP-MRD: Showing NP-Card for Decuroside III (NP0051440)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:21 UTC

Updated at

2022-04-27 22:48:22 UTC

NP-MRD ID

NP0051440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Decuroside III

Description

(2R)-2-(2-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}propan-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Decuroside III is found in Angelica decursiva and Peucedanum decursivum. Based on a literature review very few articles have been published on (2R)-2-(2-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}propan-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200482D          

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M  END

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M  END


  Mrv1652304282200482D          

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   10.7274   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7274   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9024   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2524   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2524   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4274    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 20 25  1  1  0  0  0
 26 25  1  1  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
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
 29 34  1  6  0  0  0
 28 35  1  6  0  0  0
 27 36  1  1  0  0  0
 19 37  1  1  0  0  0
 18 38  1  6  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O[C@@H]1O[C@H](CO)[C@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)[C@H]1CC2=C(O1)C=C1OC(=O)C=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O14/c1-26(2,16-6-11-5-10-3-4-17(29)36-12(10)7-13(11)35-16)40-25-22(34)20(32)23(15(9-28)38-25)39-24-21(33)19(31)18(30)14(8-27)37-24/h3-5,7,14-16,18-25,27-28,30-34H,6,8-9H2,1-2H3/t14-,15-,16-,18+,19+,20-,21-,22-,23+,24-,25+/m1/s1

> <INCHI_KEY>
FBXYOMVTZDVTHK-DNFJZVHFSA-N

> <FORMULA>
C26H34O14

> <MOLECULAR_WEIGHT>
570.544

> <EXACT_MASS>
570.194855775

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.09771815927839

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-(2-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}propan-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
-0.87

> <JCHEM_LOGP>
-1.8092776843333336

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.485732932854049

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.939478400335886

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835652988272

> <JCHEM_POLAR_SURFACE_AREA>
214.05999999999997

> <JCHEM_REFRACTIVITY>
131.1675

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-(2-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}propan-2-yl)-2H,3H-furo[3,2-g]chromen-7-one

> <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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.799   2.016   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.245   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.785   0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.555  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.095  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.865  -1.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.095  -3.231   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.555  -3.231   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.785  -1.897   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.785  -4.565   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.245  -4.565   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      13.865  -4.565   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      15.405  -4.565   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.175  -5.898   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.715  -5.898   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.485  -4.565   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.715  -3.231   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.175  -3.231   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      18.485  -1.897   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      20.025  -1.897   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      20.025  -4.565   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      18.485  -7.232   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      15.405  -7.232   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      15.405  -1.897   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.865   0.770   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.245  -0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.245   2.310   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    1                                                       
CONECT   15   13   16   39   40                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   20   37                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   36                                                  
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29                                                            
CONECT   35   28                                                            
CONECT   36   27                                                            
CONECT   37   19                                                            
CONECT   38   18                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₄

Average Mass

570.5440 Da

Monoisotopic Mass

570.19486 Da

IUPAC Name

(2R)-2-(2-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}propan-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

Traditional Name

(2R)-2-(2-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}propan-2-yl)-2H,3H-furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC(C)(O[C@@H]1O[C@H](CO)[C@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)[C@H]1CC2=C(O1)C=C1OC(=O)C=CC1=C2

InChI Identifier

InChI=1S/C26H34O14/c1-26(2,16-6-11-5-10-3-4-17(29)36-12(10)7-13(11)35-16)40-25-22(34)20(32)23(15(9-28)38-25)39-24-21(33)19(31)18(30)14(8-27)37-24/h3-5,7,14-16,18-25,27-28,30-34H,6,8-9H2,1-2H3/t14-,15-,16-,18+,19+,20-,21-,22-,23+,24-,25+/m1/s1

InChI Key

FBXYOMVTZDVTHK-DNFJZVHFSA-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
Angelica decursiva	LOTUS Database	35616633
Peucedanum decursivum MAXIM	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
O-glycosyl compound
Glycosyl compound
Disaccharide
1-benzopyran
Benzopyran
Coumaran
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Heteroaromatic compound
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	-0.87	ALOGPS
logP	-1.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	214.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	131.17 m³·mol⁻¹	ChemAxon
Polarizability	56.1 Å³	ChemAxon
Number of Rings	5	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

162987906

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Decuroside III (NP0051440)

MOL for NP0051440 (Decuroside III)

3D MOL for NP0051440 (Decuroside III)

3D SDF for NP0051440 (Decuroside III)

3D-SDF for NP0051440 (Decuroside III)

PDB for NP0051440 (Decuroside III)

3D PDB for NP0051440 (Decuroside III)

SMILES for NP0051440 (Decuroside III)

INCHI for NP0051440 (Decuroside III)

Structure for NP0051440 (Decuroside III)

3D Structure for NP0051440 (Decuroside III)