NP-MRD: Showing NP-Card for 8-Hydroxypinoresinol (NP0047595)

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Record Information

Version

2.0

Created at

2022-03-17 20:42:46 UTC

Updated at

2022-03-17 20:42:46 UTC

NP-MRD ID

NP0047595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-Hydroxypinoresinol

Description

8-Hydroxypinoresinol 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. 8-Hydroxypinoresinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 8-Hydroxypinoresinol has been detected, but not quantified in, olives and pomes. 8-Hydroxypinoresinol is found in Bauhinia tarapotensis, Carduus tenuiflorus, Echinacea purpurea, Eucommia ulmoides , Fraxinus chinensis, Fraxinus japonica , Fraxinus mandshurica var. japonica , Fraxinus micrantha, Fraxinus ornus , Fraxinus oxycarba, Gentiana lutea, Jasminum sambac , Nardostachys jatamansi , Nothapodytes foetida, Nothapodytes nimmoniana, Poraqueiba guianensis, Premna resinosa , Saussurea lappa , Schisandra lancifolia, Sorbaria sorbifolia var. stellipila , Stauntonia hexaphylla , Strophanthus gratus , Swertia elongata, Valeriana carnosa, Valeriana laxiflora, Valeriana microphylla, Valeriana officinalis and Valeriana prionophylla . This could make 8-hydroxypinoresinol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307022D          

 27 30  0  0  0  0            999 V2000
    5.2175   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4063    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666    1.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    1.3686    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
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047    2.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    2.1533    0.0000 C   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
    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  0  0  0  0  0  0  0  0  0  0
    3.8585   -4.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498    3.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626   -2.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    2.3248    0.0000 O   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
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 15  2  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 20 10  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 20  1  0  0  0  0
 24  1  1  0  0  0  0
 24 16  1  0  0  0  0
 25  2  1  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 26 19  1  0  0  0  0
 27 10  1  0  0  0  0
 27 18  1  0  0  0  0
M  END


  Mrv0541 05061307022D          

 27 30  0  0  0  0            999 V2000
    5.2175   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4063    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666    1.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    1.3686    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
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047    2.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    2.1533    0.0000 C   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
    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  0  0  0  0  0  0  0  0  0  0
    3.8585   -4.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498    3.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626   -2.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    2.3248    0.0000 O   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
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 15  2  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 20 10  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 20  1  0  0  0  0
 24  1  1  0  0  0  0
 24 16  1  0  0  0  0
 25  2  1  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 26 19  1  0  0  0  0
 27 10  1  0  0  0  0
 27 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1OCC2(O)C1COC2C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O7/c1-24-16-7-11(3-5-14(16)21)18-13-9-26-19(20(13,23)10-27-18)12-4-6-15(22)17(8-12)25-2/h3-8,13,18-19,21-23H,9-10H2,1-2H3

> <INCHI_KEY>
CICMVLOHBZPXIT-UHFFFAOYSA-N

> <FORMULA>
C20H22O7

> <MOLECULAR_WEIGHT>
374.3845

> <EXACT_MASS>
374.136553058

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
37.92946008394322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-ol

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.7277508563333335

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.209308533296317

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.608053406667167

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8193758474211594

> <JCHEM_POLAR_SURFACE_AREA>
97.61000000000001

> <JCHEM_REFRACTIVITY>
95.98129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-bis(4-hydroxy-3-methoxyphenyl)-tetrahydro-1H-furo[3,4-c]furan-3a-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.739  -6.756   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.625   3.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.745  -4.331   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.924   3.379   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.220  -5.795   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.449   4.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.281  -3.507   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.388   2.555   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.775  -3.186   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.894   2.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.835  -1.246   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.727  -6.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.942   5.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.757  -4.971   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.088   4.019   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.835   0.294   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.203  -7.580   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.466   6.629   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.835   1.834   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.264  -5.291   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.595   4.340   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   25                                                            
CONECT    3    5   11                                                       
CONECT    4    6   12                                                       
CONECT    5    3   14                                                       
CONECT    6    4   15                                                       
CONECT    7   11   16                                                       
CONECT    8   12   17                                                       
CONECT    9   13   26                                                       
CONECT   10   20   27                                                       
CONECT   11    3    7   18                                                  
CONECT   12    4    8   19                                                  
CONECT   13    9   18   20                                                  
CONECT   14    5   16   21                                                  
CONECT   15    6   17   22                                                  
CONECT   16    7   14   24                                                  
CONECT   17    8   15   25                                                  
CONECT   18   11   13   27                                                  
CONECT   19   12   20   26                                                  
CONECT   20   10   13   19   23                                             
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   20                                                            
CONECT   24    1   16                                                       
CONECT   25    2   17                                                       
CONECT   26    9   19                                                       
CONECT   27   10   18                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
(+)-8(1)-Hydroxypinoresinol	HMDB
1-Hydroxypinoresinol	HMDB
2,6-Bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-1-ol	HMDB
4,4',8-Trihydroxy-3,3'-dimethoxy-7,9':7',9-diepoxylignan	HMDB

Chemical Formula

C₂₀H₂₂O₇

Average Mass

374.3845 Da

Monoisotopic Mass

374.13655 Da

IUPAC Name

1,4-bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-ol

Traditional Name

1,4-bis(4-hydroxy-3-methoxyphenyl)-tetrahydro-1H-furo[3,4-c]furan-3a-ol

CAS Registry Number

81426-17-7

SMILES

COC1=C(O)C=CC(=C1)C1OCC2(O)C1COC2C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C20H22O7/c1-24-16-7-11(3-5-14(16)21)18-13-9-26-19(20(13,23)10-27-18)12-4-6-15(22)17(8-12)25-2/h3-8,13,18-19,21-23H,9-10H2,1-2H3

InChI Key

CICMVLOHBZPXIT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bauhinia tarapotensis	Plant	KNApSAcK
Carduus tenuiflorus	LOTUS Database	35616633
Echinacea purpurea	LOTUS Database	35616633
Eucommia ulmoides	Plant	KNApSAcK
Fraxinus chinensis	LOTUS Database	35616633
Fraxinus japonica	Plant	KNApSAcK
Fraxinus mandshurica var. japonica	Plant	KNApSAcK
Fraxinus micrantha	Plant	KNApSAcK
Fraxinus ornus	Plant	KNApSAcK
Fraxinus oxycarba	Plant	KNApSAcK
Gentiana lutea	LOTUS Database	35616633
Jasminum sambac	Plant	KNApSAcK
Nardostachys jatamansi	Plant	KNApSAcK
Nothapodytes foetida	Plant	KNApSAcK
Nothapodytes nimmoniana	LOTUS Database	35616633
Olea europaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Poraqueiba guianensis	Plant	KNApSAcK
Premna resinosa	Plant	KNApSAcK
Saussurea costus	Plant	KNApSAcK
Schisandra lancifolia	LOTUS Database	35616633
Sorbaria sorbifolia var. stellipila	Plant	KNApSAcK
Stauntonia hexaphylla	Plant	KNApSAcK
Strophanthus gratus	Plant	KNApSAcK
Swertia elongata	Plant	KNApSAcK
Valeriana carnosa	LOTUS Database	35616633
Valeriana laxiflora	Plant	KNApSAcK
Valeriana microphylla	LOTUS Database	35616633
Valeriana officinalis	Plant	KNApSAcK
Valeriana prionophylla	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
Methoxyphenol
Phenoxy compound
Anisole
Furofuran
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Tetrahydrofuran
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
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	1.8	ALOGPS
logP	1.73	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.61	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	97.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.98 m³·mol⁻¹	ChemAxon
Polarizability	37.93 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	No	ChemAxon

External Links

HMDB ID

HMDB0033279

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011302

KNApSAcK ID

C00007191

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

13824420

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8-Hydroxypinoresinol (NP0047595)

MOL for NP0047595 (8-Hydroxypinoresinol)

3D MOL for NP0047595 (8-Hydroxypinoresinol)

3D SDF for NP0047595 (8-Hydroxypinoresinol)

3D-SDF for NP0047595 (8-Hydroxypinoresinol)

PDB for NP0047595 (8-Hydroxypinoresinol)

3D PDB for NP0047595 (8-Hydroxypinoresinol)

SMILES for NP0047595 (8-Hydroxypinoresinol)

INCHI for NP0047595 (8-Hydroxypinoresinol)

Structure for NP0047595 (8-Hydroxypinoresinol)

3D Structure for NP0047595 (8-Hydroxypinoresinol)