NP-MRD: Showing NP-Card for (+)-Epieudesmin (NP0050465)

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Record Information

Version

2.0

Created at

2022-04-27 21:44:27 UTC

Updated at

2022-04-27 21:44:27 UTC

NP-MRD ID

NP0050465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Epieudesmin

Description

(+)-Epieudesmin 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. (+)-Epieudesmin is found in Achillea holosericea, Artemisia absinthium, Daphne oleoides ssp. oleoides , Forsythia sp., Gmelina arborea , Haplophyllum acutifolium , Hernandia nymphaeifolia , Hernandia sonora, Lindera praecox, Magnolia biondii, Magnolia coco, Orophea enneandra, Ouratea semiserrata, Parabenzoin praecox, Persea kurzii, Raulinoa echinata, Samadera bidwillii, Zanthoxylum acanthopodium , Zanthoxylum alatum , Zanthoxylum culantrillo, Zanthoxylum fagara and Zanthoxylum oxyphyllum . Based on a literature review very few articles have been published on (+)-epieudesmin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223442D          

 28 31  0  0  1  0            999 V2000
   -1.3168    1.7408    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
    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
   -0.0000   -0.0000    0.0000 C   0  0  1  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  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  2  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  1  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0370   -5.0865    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
    1.4012    2.6239    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
   -1.8267    3.3100    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
  7  5  1  6  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
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv1652304272223442D          

 28 31  0  0  1  0            999 V2000
   -1.3168    1.7408    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
    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
   -0.0000   -0.0000    0.0000 C   0  0  1  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  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  2  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  1  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0370   -5.0865    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
    1.4012    2.6239    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
   -1.8267    3.3100    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
  7  5  1  6  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
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)[C@H]1OC[C@H]2[C@@H]1CO[C@H]2C1=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+/m0/s1

> <INCHI_KEY>
PEUUVVGQIVMSAW-WWLNLUSPSA-N

> <FORMULA>
C22H26O6

> <MOLECULAR_WEIGHT>
386.444

> <EXACT_MASS>
386.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.14755495838559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
2.569547659333333

> <ALOGPS_LOGS>
-4.85

> <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>
104.06479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.46e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.428   4.394   0.000  0.00  0.00           C+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      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.905  -1.246   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.834  -1.246   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.911  -4.277   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.387  -5.741   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.357  -6.886   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.851  -6.565   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.375  -5.101   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.820  -7.710   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.314  -7.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.833  -8.350   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.802  -9.495   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.109   5.218   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.615   4.898   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.904   5.859   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.410   6.179   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   27                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18   24                                                       
CONECT   24   23                                                            
CONECT   25    3   26                                                       
CONECT   26   25                                                            
CONECT   27    2   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

(1R,3aR,4S,6aR)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan

Traditional Name

(1R,3aR,4S,6aR)-1,4-bis(3,4-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)[C@H]1OC[C@H]2[C@@H]1CO[C@H]2C1=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+/m0/s1

InChI Key

PEUUVVGQIVMSAW-WWLNLUSPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea holosericea	LOTUS Database	35616633
Artemisia absinthium	LOTUS Database	35616633
Daphne oleoides ssp. oleoides	Plant	KNApSAcK
Forsythia sp.	Plant	KNApSAcK
Gmelina arborea	Plant	KNApSAcK
Haplophyllum acutifolium	Plant	KNApSAcK
Hernandia nymphaeifolia	Plant	KNApSAcK
Hernandia sonora	LOTUS Database	35616633
Lindera praecox	LOTUS Database	35616633
Magnolia biondii	LOTUS Database	35616633
Magnolia coco	Plant	KNApSAcK
Orophea enneandra	Plant	KNApSAcK
Ouratea semiserrata	Plant	KNApSAcK
Parabenzoin praecox	Plant	KNApSAcK
Persea kurzii	Plant	KNApSAcK
Raulinoa echinata	Plant	KNApSAcK
Samadera bidwillii	LOTUS Database	35616633
Zanthoxylum acanthopodium	Plant	KNApSAcK
Zanthoxylum alatum	Plant	KNApSAcK
Zanthoxylum culantrillo	Plant	KNApSAcK
Zanthoxylum fagara	Plant	KNApSAcK
Zanthoxylum oxyphyllum	Plant	KNApSAcK

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
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenoxy compound
Furofuran
Phenol ether
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxolane
Ether
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	2.97	ALOGPS
logP	2.57	ChemAxon
logS	-4.8	ALOGPS
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	41.15 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

5367720

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7000209

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Epieudesmin (NP0050465)

MOL for NP0050465 ((+)-Epieudesmin)

3D MOL for NP0050465 ((+)-Epieudesmin)

3D SDF for NP0050465 ((+)-Epieudesmin)

3D-SDF for NP0050465 ((+)-Epieudesmin)

PDB for NP0050465 ((+)-Epieudesmin)

3D PDB for NP0050465 ((+)-Epieudesmin)

SMILES for NP0050465 ((+)-Epieudesmin)

INCHI for NP0050465 ((+)-Epieudesmin)

Structure for NP0050465 ((+)-Epieudesmin)

3D Structure for NP0050465 ((+)-Epieudesmin)