NP-MRD: Showing NP-Card for (3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan (NP0222759)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 00:40:49 UTC

Updated at

2022-09-06 00:40:49 UTC

NP-MRD ID

NP0222759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan

Description

(3AS,6aS)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. (3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan is found in Aglaia leptantha, Bupleurum salicifolium, Daphne oleoides, Geranium platyanthum, Haplophyllum acutifolium, Lindera praecox, Liriodendron tulipifera, Magnolia biondii, Magnolia coco, Magnolia denudata, Magnolia stellata, Metrodorea flavida, Metrodorea nigra, Pandanus odoratissimus, Annona mucosa and Annona sylvatica. Based on a literature review very few articles have been published on (3aS,6aS)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202402D          

 28 31  0  0  1  0            999 V2000
    0.8018   -4.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -4.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    1.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036    2.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    3.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3065    4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626    2.3248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007    1.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -3.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.5024    0.0000 C   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
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 12 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
  7 24  1  0  0  0  0
 10 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv1652309062202402D          

 28 31  0  0  1  0            999 V2000
    0.8018   -4.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -4.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    1.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036    2.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8585    3.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3065    4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626    2.3248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007    1.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -3.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.5024    0.0000 C   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
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 12 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
  7 24  1  0  0  0  0
 10 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C1OC[C@@H]2[C@H]1COC2C1=CC=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-28-22(16(15)12-27-21)14-6-8-18(24-2)20(10-14)26-4/h5-10,15-16,21-22H,11-12H2,1-4H3/t15-,16-,21?,22?/m1/s1

> <INCHI_KEY>
PEUUVVGQIVMSAW-KILAXVPQSA-N

> <FORMULA>
C22H26O6

> <MOLECULAR_WEIGHT>
386.444

> <EXACT_MASS>
386.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.976214182480305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6aS)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan

> <JCHEM_LOGP>
2.569547659333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7383009447365905

> <JCHEM_POLAR_SURFACE_AREA>
55.38000000000001

> <JCHEM_REFRACTIVITY>
104.06480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6aS)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan

> <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       1.497  -8.725   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.466  -7.580   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.942  -6.116   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.388  -3.507   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.775   2.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.744   3.379   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.220   4.844   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.727   5.164   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.203   6.629   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.172   7.773   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.757   4.019   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.264   4.340   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.294   3.195   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.281   2.555   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.924  -4.331   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.449  -5.795   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.479  -6.940   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.003  -8.405   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   12                                                       
CONECT   22   11   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    7   10                                                  
CONECT   25    6   26                                                       
CONECT   26   25    3   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₆

Average Mass

386.4440 Da

Monoisotopic Mass

386.17294 Da

IUPAC Name

(3aS,6aS)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan

Traditional Name

(3aS,6aS)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C1OC[C@@H]2[C@H]1COC2C1=CC=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C22H26O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-28-22(16(15)12-27-21)14-6-8-18(24-2)20(10-14)26-4/h5-10,15-16,21-22H,11-12H2,1-4H3/t15-,16-,21?,22?/m1/s1

InChI Key

PEUUVVGQIVMSAW-KILAXVPQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aglaia leptantha	LOTUS Database	35616633
Bupleurum salicifolium	LOTUS Database	35616633
Daphne oleoides	LOTUS Database	35616633
Geranium platyanthum	LOTUS Database	35616633
Haplophyllum acutifolium	LOTUS Database	35616633
Lindera praecox	LOTUS Database	35616633
Liriodendron tulipifera	LOTUS Database	35616633
Magnolia biondii	LOTUS Database	35616633
Magnolia coco	LOTUS Database	35616633
Magnolia denudata	LOTUS Database	35616633
Magnolia stellata	LOTUS Database	35616633
Metrodorea flavida	LOTUS Database	35616633
Metrodorea nigra	LOTUS Database	35616633
Pandanus odoratissimus	LOTUS Database	35616633
Rollinia mucosa	LOTUS Database	35616633
Rollinia sylvatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Substituents

Furanoid lignan
Furofuran lignan skeleton
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Methoxybenzene
Phenol ether
Furofuran
Anisole
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
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	2.57	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.06 m³·mol⁻¹	ChemAxon
Polarizability	40.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

78431777

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

137795855

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan (NP0222759)

MOL for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

3D MOL for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

3D SDF for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

3D-SDF for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

PDB for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

3D PDB for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

SMILES for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

INCHI for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

Structure for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)

3D Structure for NP0222759 ((3as,6as)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan)