NP-MRD: Showing NP-Card for 9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one (NP0193750)

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Record Information

Version

2.0

Created at

2022-09-04 11:17:26 UTC

Updated at

2022-09-04 11:17:26 UTC

NP-MRD ID

NP0193750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one

Description

Fesumtuorin D 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. 9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one is found in Ferula sumbul. Based on a literature review very few articles have been published on Fesumtuorin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042213172D          

 42 49  0  0  1  0            999 V2000
    4.2712   10.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042213172D          

 42 49  0  0  1  0            999 V2000
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    4.7402    3.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0258    4.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4547    4.4081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1692    3.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9307    6.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5182    6.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1770    7.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1856    7.7401    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  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  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
  8 16  2  0  0  0  0
 12 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  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  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  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
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 25 38  1  0  0  0  0
 32 38  2  0  0  0  0
 22 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
 19 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC1COC1=C2OC=CC2=CC2=C1O[C@]1(O[C@@H](COC3=C4OC=CC4=CC4=C3OC(=O)C=C4)C(C)(C)O1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C32H28O10/c1-30(2)21(39-30)15-37-29-25-20(9-12-35-25)14-18-7-10-32(41-27(18)29)40-22(31(3,4)42-32)16-36-28-24-19(8-11-34-24)13-17-5-6-23(33)38-26(17)28/h5-14,21-22H,15-16H2,1-4H3/t21?,22-,32+/m0/s1

> <INCHI_KEY>
DGFLEVFPESLTBR-HJMAHHELSA-N

> <FORMULA>
C32H28O10

> <MOLECULAR_WEIGHT>
572.566

> <EXACT_MASS>
572.168247102

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.2271216698199

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-{[(2S,5S)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromene]-5-yl]methoxy}-7H-furo[3,2-g]chromen-7-one

> <JCHEM_LOGP>
5.455541199333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5952132711838627

> <JCHEM_POLAR_SURFACE_AREA>
111.26000000000002

> <JCHEM_REFRACTIVITY>
149.0246

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
9-[(2S,5S)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromene]-5-ylmethoxy]furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.973  19.503   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.509  19.610   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.882  18.116   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.670  21.142   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.916  20.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.448  20.076   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.074  18.669   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.606  18.508   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.232  17.101   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.764  16.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.669  18.186   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.042  19.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.669  21.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.524  22.030   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.191  21.260   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      15.511  19.754   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.390  15.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.485  14.287   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.953  14.448   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.327  15.855   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      15.429  12.984   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.183  12.078   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.183  10.538   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.849   9.768   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.849   8.228   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.183   7.458   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.648   7.934   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      16.553   6.688   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.648   5.443   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.183   5.918   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.849   5.148   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.516   5.918   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.182   5.148   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.848   5.918   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.848   7.458   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.515   8.228   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.182   8.228   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      11.516   7.458   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.937  12.984   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.167  11.650   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.530  13.610   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      13.413  14.448   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    2    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8   12                                                  
CONECT   17   10   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   42                                             
CONECT   20   19    9                                                       
CONECT   21   19   22                                                       
CONECT   22   21   23   39                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   25   32                                                  
CONECT   39   22   40   41   42                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   39   19                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₈O₁₀

Average Mass

572.5660 Da

Monoisotopic Mass

572.16825 Da

IUPAC Name

9-{[(2S,5S)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromene]-5-yl]methoxy}-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-[(2S,5S)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromene]-5-ylmethoxy]furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC1COC1=C2OC=CC2=CC2=C1O[C@]1(O[C@@H](COC3=C4OC=CC4=CC4=C3OC(=O)C=C4)C(C)(C)O1)C=C2

InChI Identifier

InChI=1S/C32H28O10/c1-30(2)21(39-30)15-37-29-25-20(9-12-35-25)14-18-7-10-32(41-27(18)29)40-22(31(3,4)42-32)16-36-28-24-19(8-11-34-24)13-17-5-6-23(33)38-26(17)28/h5-14,21-22H,15-16H2,1-4H3/t21?,22-,32+/m0/s1

InChI Key

DGFLEVFPESLTBR-HJMAHHELSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ferula sumbul	LOTUS Database	35616633

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
Benzopyran
1-benzopyran
Benzofuran
Phenol ether
Alkyl aryl ether
Carboxylic acid orthoester
Pyranone
Ortho ester
Benzenoid
Pyran
Meta-dioxolane
Heteroaromatic compound
Furan
Orthocarboxylic acid derivative
Lactone
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	5.46	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	149.02 m³·mol⁻¹	ChemAxon
Polarizability	57.23 Å³	ChemAxon
Number of Rings	8	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

C00037148

Chemspider ID

424031

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

483512

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one (NP0193750)

MOL for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

3D MOL for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

3D SDF for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

3D-SDF for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

PDB for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

3D PDB for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

SMILES for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

INCHI for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

Structure for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)

3D Structure for NP0193750 (9-[(2s,5s)-9'-[(3,3-dimethyloxiran-2-yl)methoxy]-4,4-dimethylspiro[1,3-dioxolane-2,7'-furo[3,2-g]chromen]-5-ylmethoxy]furo[3,2-g]chromen-7-one)