NP-MRD: Showing NP-Card for 4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one (NP0246726)

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Record Information

Version

2.0

Created at

2022-09-07 08:17:16 UTC

Updated at

2022-09-07 08:17:16 UTC

NP-MRD ID

NP0246726

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one

Description

ACMC-20dhky 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. 4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one is found in Acorus calamus, Daldinia concentrica, Linum usitatissimum, Peperomia heyneana and Rhaphidophora decursiva. ACMC-20dhky is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.0407    3.5913    2.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0895    3.2467    1.4407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584    2.0290    0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2909    1.0486    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403   -0.1660    0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6271   -1.2186    0.2525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1085   -1.3584    1.5345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680   -1.5005    1.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9774   -1.1525    0.1510 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7210   -2.2759   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9229   -2.5639   -0.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8118   -2.9057   -1.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671   -1.9551   -1.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509   -0.9465   -0.6763 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6207   -0.3502   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    0.5973   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8004    0.3965   -1.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0030   -0.8311   -1.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4307    1.8193    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035    2.8066    0.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9430    3.2996    1.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842    4.6694    2.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0325    3.1000    3.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6126    1.2745    1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1567   -2.1921   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8843   -0.7686    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8278   -2.5130    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746   -0.2187    0.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8825   -2.4278   -1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2378   -1.4356   -2.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6471    0.0758   -1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460   -1.3000   -0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536   -0.7657   -2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877   -1.6271   -1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175   -1.1474   -2.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172    3.6658    0.5456 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  1  0
 17 18  1  0
 16 19  2  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
 19  3  1  0
 14  6  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
 18 33  1  0
 18 34  1  0
 18 35  1  0
 20 36  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


  Mrv1533004151516542D          

 20 22  0  0  0  0            999 V2000
    0.3392    3.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942    2.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    0.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    1.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    1.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3788    2.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648    2.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    3.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    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
  5  6  2  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
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0246726

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O6/c1-17-10-3-7(4-11(18-2)12(10)15)13-8-5-20-14(16)9(8)6-19-13/h3-4,8-9,13,15H,5-6H2,1-2H3

> <INCHI_KEY>
AUXYOVQIZNPKSO-UHFFFAOYSA-N

> <FORMULA>
C14H16O6

> <MOLECULAR_WEIGHT>
280.276

> <EXACT_MASS>
280.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.529932504227553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-one

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
0.7086532706666666

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.302986918853017

> <JCHEM_PKA_STRONGEST_BASIC>
-4.044295843591029

> <JCHEM_POLAR_SURFACE_AREA>
74.22

> <JCHEM_REFRACTIVITY>
68.6388

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3H-furo[3,4-c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       0.633   6.683   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.109   5.218   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.079   4.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.555   2.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.476   1.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.982   1.785   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.964   3.570   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.440   5.034   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.428   4.394   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.904   5.859   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.905  -1.246   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.834  -1.246   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.405  -3.956   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-(3',5'-Dimethoxy-4'-hydroxyphenyl)-3,7-dioxoabicyclo(3.3.0)octan-6-one	MeSH
Zhepeiresinol	MeSH

Chemical Formula

C₁₄H₁₆O₆

Average Mass

280.2760 Da

Monoisotopic Mass

280.09469 Da

IUPAC Name

4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-one

Traditional Name

4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3H-furo[3,4-c]furan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2=O

InChI Identifier

InChI=1S/C14H16O6/c1-17-10-3-7(4-11(18-2)12(10)15)13-8-5-20-14(16)9(8)6-19-13/h3-4,8-9,13,15H,5-6H2,1-2H3

InChI Key

AUXYOVQIZNPKSO-UHFFFAOYSA-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
Acorus calamus	LOTUS Database	35616633
Daldinia concentrica	LOTUS Database	35616633
Linum usitatissimum	LOTUS Database	35616633
Peperomia heyneana	LOTUS Database	35616633
Rhaphidophora decursiva	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

Lignan lactone
Furanoid lignan
Furofuran lignan skeleton
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Phenoxy compound
Furofuran
Phenol ether
Anisole
Methoxybenzene
Phenol
Alkyl aryl ether
Benzenoid
Gamma butyrolactone
Monocyclic benzene moiety
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen 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	0.92	ALOGPS
logP	0.71	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.64 m³·mol⁻¹	ChemAxon
Polarizability	27.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

5315434

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one (NP0246726)

MOL for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D MOL for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D SDF for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D-SDF for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

PDB for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D PDB for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

SMILES for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

INCHI for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

Structure for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

3D Structure for NP0246726 (4-(4-hydroxy-3,5-dimethoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)