NP-MRD: Showing NP-Card for 4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol (NP0321796)

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Record Information

Version

2.0

Created at

2022-09-12 00:11:33 UTC

Updated at

2022-09-12 00:11:34 UTC

NP-MRD ID

NP0321796

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol

Description

4-[(1R,3aS,4R,6aS)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol 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. 4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol is found in Carya cathayensis and Zanthoxylum wutaiense. Based on a literature review very few articles have been published on 4-[(1R,3aS,4R,6aS)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    6.9833   -0.6105    0.2234 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6322   -0.3116    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7781   -1.1397   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4246   -0.8250   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375    0.3224   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4876    0.6936   -0.1872 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1386    1.1345    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2519    1.1120    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5644   -0.2086    0.4547 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6916   -0.5818   -0.3471 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1443   -0.7670   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117   -1.0392   -1.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578   -0.0067   -0.6604 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9540   -0.0402   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7562    1.0839   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0800    1.0200    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6607   -0.1648    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9949   -0.2262    1.0448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8602   -1.2867    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -1.2255    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370    1.1478    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1659    0.8426    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5801   -0.2453   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.0606   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564   -1.4938   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    1.4366   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6990    1.2516    2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    1.9523    0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8129   -1.0070    1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1796   -1.4629    0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6447   -1.5400   -2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1894    0.2097   -2.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756    0.9372   -1.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013    2.0245   -0.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7016    1.9158    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2145   -0.0914    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3145   -2.2301    0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -2.1052    0.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4321    2.0575    1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8075    1.5277    1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 21  1  0
 21 22  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 22  2  1  0
 10  6  1  0
 20 14  1  0
 13  9  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
 21 39  1  0
 22 40  1  0
  6 26  1  6
  8 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  1
 11 31  1  0
 11 32  1  0
 13 33  1  6
 15 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END


  Mrv1652309122202112D          

 22 25  0  0  1  0            999 V2000
   -1.0198    3.1385    0.0000 O   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
   -0.0000   -0.0000    0.0000 C   0  0  2  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  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  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
    2.5890   -4.4734    0.0000 O   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
   -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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321796

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O4/c19-13-5-1-11(2-6-13)17-15-9-22-18(16(15)10-21-17)12-3-7-14(20)8-4-12/h1-8,15-20H,9-10H2/t15-,16-,17+,18+/m1/s1

> <INCHI_KEY>
AYMLHOROIXAYPH-BDXSIMOUSA-N

> <FORMULA>
C18H18O4

> <MOLECULAR_WEIGHT>
298.338

> <EXACT_MASS>
298.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.208353319070202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1R,3aS,4R,6aS)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol

> <JCHEM_LOGP>
2.593102078666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.773196752992696

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.171136761664751

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8805313577254554

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
82.17380000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1R,3aS,4R,6aS)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.904   5.859   0.000  0.00  0.00           O+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      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.905  -1.246   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.834  -1.246   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.911  -4.277   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.387  -5.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.357  -6.886   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.833  -8.350   0.000  0.00  0.00           O+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  C   UNK     0      -1.982   1.785   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
CONECT   21    5   22                                                       
CONECT   22   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₄

Average Mass

298.3380 Da

Monoisotopic Mass

298.12051 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H18O4/c19-13-5-1-11(2-6-13)17-15-9-22-18(16(15)10-21-17)12-3-7-14(20)8-4-12/h1-8,15-20H,9-10H2/t15-,16-,17+,18+/m1/s1

InChI Key

AYMLHOROIXAYPH-BDXSIMOUSA-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
Carya cathayensis	LOTUS Database	35616633
Zanthoxylum wutaiense	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
Furofuran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Oxolane
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
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

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

10308001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21722914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol (NP0321796)

MOL for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

3D MOL for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

3D SDF for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

3D-SDF for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

PDB for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

3D PDB for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

SMILES for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

INCHI for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

Structure for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)

3D Structure for NP0321796 (4-[(1r,3as,4r,6as)-4-(4-hydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]phenol)