NP-MRD: Showing NP-Card for (3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one (NP0233201)

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Record Information

Version

2.0

Created at

2022-09-06 14:43:08 UTC

Updated at

2022-09-06 14:43:08 UTC

NP-MRD ID

NP0233201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one

Description

(3AR,4S,6aR)-4-(7-methoxy-2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-one belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. (3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one is found in Nectandra turbacensis. Based on a literature review very few articles have been published on (3aR,4S,6aR)-4-(7-methoxy-2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
    3.2278   -2.5877   -1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -1.2812   -0.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5615   -0.4444   -0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -0.8469   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -0.0330    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909   -0.4984    0.3070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8198   -0.1539    1.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1908   -0.2111    1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2078    0.6409   -0.0840 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3496    0.3474   -0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4903    0.8577   -0.8385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9865   -0.5798   -1.8846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229   -0.9718   -1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047    0.0905   -0.8117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5890    1.2451    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986    1.6822    0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9010    0.8407    0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1303    1.4638    0.2554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827    2.8456    0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428    2.8684    0.9835 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5894   -3.1242   -0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -3.1305   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173   -2.5900   -2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022   -1.8472   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1890   -1.6071    0.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4672   -1.2566    0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032    0.2204    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0987    1.6908    0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1024   -1.0665   -2.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6055   -1.9390   -1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4679    0.8588   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.9009    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984    3.2746    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419    3.3416   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 17  3  1  0
 14  6  1  0
 20 16  1  0
 10  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
 15 32  1  0
 19 33  1  0
 19 34  1  0
  6 25  1  6
  8 26  1  0
  8 27  1  0
  9 28  1  1
 14 31  1  6
 13 29  1  0
 13 30  1  0
M  END


  Mrv1652309062216432D          

 20 23  0  0  1  0            999 V2000
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4615   -0.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0136   -0.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6011   -1.4045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6873   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018   -2.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -2.5605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3816   -1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941   -1.2330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC2=C1OCO2)[C@H]1OC[C@H]2[C@@H]1COC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O6/c1-16-10-2-7(3-11-13(10)20-6-19-11)12-8-4-18-14(15)9(8)5-17-12/h2-3,8-9,12H,4-6H2,1H3/t8-,9-,12+/m0/s1

> <INCHI_KEY>
ZANKSPPCAFPVGD-HOTUBEGUSA-N

> <FORMULA>
C14H14O6

> <MOLECULAR_WEIGHT>
278.26

> <EXACT_MASS>
278.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.99344867582961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aR)-4-(7-methoxy-2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-one

> <JCHEM_LOGP>
0.7931233256666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.025550215352215

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
65.96160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aR)-4-(7-methoxy-2H-1,3-benzodioxol-5-yl)-tetrahydro-3H-furo[3,4-c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.195  -0.144   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.225  -1.288   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.455  -2.622   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.616  -4.153   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.950  -4.923   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.209  -4.780   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.179  -3.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.949  -2.302   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6    9                                                  
CONECT   15    5   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16    3   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₄O₆

Average Mass

278.2600 Da

Monoisotopic Mass

278.07904 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC2=C1OCO2)[C@H]1OC[C@H]2[C@@H]1COC2=O

InChI Identifier

InChI=1S/C14H14O6/c1-16-10-2-7(3-11-13(10)20-6-19-11)12-8-4-18-14(15)9(8)5-17-12/h2-3,8-9,12H,4-6H2,1H3/t8-,9-,12+/m0/s1

InChI Key

ZANKSPPCAFPVGD-HOTUBEGUSA-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
Nectandra turbacensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Not Available

Direct Parent

Lignan lactones

Alternative Parents

Substituents

Furanoid lignan
Lignan lactone
Furofuran lignan skeleton
Benzodioxole
Anisole
Furofuran
Alkyl aryl ether
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
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

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

162886797

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one (NP0233201)

MOL for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D MOL for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D SDF for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D-SDF for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

PDB for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D PDB for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

SMILES for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

INCHI for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

Structure for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D Structure for NP0233201 ((3ar,4s,6ar)-4-(7-methoxy-2h-1,3-benzodioxol-5-yl)-tetrahydro-3h-furo[3,4-c]furan-1-one)