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Showing NP-Card for 8-Acetoxypinoresinol (NP0047596)

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Record Information
Version2.0
Created at2022-03-17 20:42:47 UTC
Updated at2022-03-17 20:42:47 UTC
NP-MRD IDNP0047596
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-Acetoxypinoresinol
Description8-Acetoxypinoresinol 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-Acetoxypinoresinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 8-Acetoxypinoresinol is found, on average, in the highest concentration within olives. 8-Acetoxypinoresinol has also been detected, but not quantified in, a few different foods, such as fats and oils, herbs and spices, and pomes. This could make 8-acetoxypinoresinol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047596 (8-Acetoxypinoresinol)


  Mrv0541 05061307022D          

 30 33  0  0  0  0            999 V2000
    3.4831    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.7686    1.3951    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
    2.7686    2.2201    0.0000 O   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
    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
    2.0542    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
 12  1  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
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 15 10  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 18 16  2  0  0  0  0
 19  9  1  0  0  0  0
 19 17  2  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 14  1  0  0  0  0
 22 11  1  0  0  0  0
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 22 21  1  0  0  0  0
 23 12  2  0  0  0  0
 24 16  1  0  0  0  0
 25 17  1  0  0  0  0
 26  2  1  0  0  0  0
 26 18  1  0  0  0  0
 27  3  1  0  0  0  0
 27 19  1  0  0  0  0
 28 10  1  0  0  0  0
 28 21  1  0  0  0  0
 29 11  1  0  0  0  0
 29 20  1  0  0  0  0
 30 12  1  0  0  0  0
 30 22  1  0  0  0  0
M  END
Download

3D MOL for NP0047596 (8-Acetoxypinoresinol)

Download
3D SDF for NP0047596 (8-Acetoxypinoresinol)

  Mrv0541 05061307022D          

 30 33  0  0  0  0            999 V2000
    3.4831    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.7686    1.3951    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
    2.7686    2.2201    0.0000 O   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
    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
    2.0542    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
 12  1  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 18 16  2  0  0  0  0
 19  9  1  0  0  0  0
 19 17  2  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 14  1  0  0  0  0
 22 11  1  0  0  0  0
 22 15  1  0  0  0  0
 22 21  1  0  0  0  0
 23 12  2  0  0  0  0
 24 16  1  0  0  0  0
 25 17  1  0  0  0  0
 26  2  1  0  0  0  0
 26 18  1  0  0  0  0
 27  3  1  0  0  0  0
 27 19  1  0  0  0  0
 28 10  1  0  0  0  0
 28 21  1  0  0  0  0
 29 11  1  0  0  0  0
 29 20  1  0  0  0  0
 30 12  1  0  0  0  0
 30 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047596

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O8/c1-12(23)30-22-11-29-20(13-4-6-16(24)18(8-13)26-2)15(22)10-28-21(22)14-5-7-17(25)19(9-14)27-3/h4-9,15,20-21,24-25H,10-11H2,1-3H3

> <INCHI_KEY>
NATDFORNCKZPCI-UHFFFAOYSA-N

> <FORMULA>
C22H24O8

> <MOLECULAR_WEIGHT>
416.4212

> <EXACT_MASS>
416.147117744

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
42.122504196108025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.168876266666666

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.210536917701788

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.608473826521905

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8192924754612103

> <JCHEM_POLAR_SURFACE_AREA>
103.68000000000002

> <JCHEM_REFRACTIVITY>
105.13279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.88e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047596 (8-Acetoxypinoresinol)
Download
PDB for NP0047596 (8-Acetoxypinoresinol)
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       6.502   1.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.739  -6.756   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.625   3.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.745  -4.331   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.924   3.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.220  -5.795   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.449   4.844   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.281  -3.507   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.388   2.555   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.370  -1.722   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       5.168   2.604   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.775  -3.186   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.894   2.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.835  -1.246   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.727  -6.116   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.942   5.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.757  -4.971   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.088   4.019   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.835   0.294   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.168   4.144   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.203  -7.580   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.466   6.629   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.264  -5.291   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.595   4.340   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.835   1.834   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   26                                                            
CONECT    3   27                                                            
CONECT    4    6   13                                                       
CONECT    5    7   14                                                       
CONECT    6    4   16                                                       
CONECT    7    5   17                                                       
CONECT    8   13   18                                                       
CONECT    9   14   19                                                       
CONECT   10   15   28                                                       
CONECT   11   22   29                                                       
CONECT   12    1   23   30                                                  
CONECT   13    4    8   20                                                  
CONECT   14    5    9   21                                                  
CONECT   15   10   20   22                                                  
CONECT   16    6   18   24                                                  
CONECT   17    7   19   25                                                  
CONECT   18    8   16   26                                                  
CONECT   19    9   17   27                                                  
CONECT   20   13   15   29                                                  
CONECT   21   14   22   28                                                  
CONECT   22   11   15   21   30                                             
CONECT   23   12                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26    2   18                                                       
CONECT   27    3   19                                                       
CONECT   28   10   21                                                       
CONECT   29   11   20                                                       
CONECT   30   12   22                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

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3D PDB for NP0047596 (8-Acetoxypinoresinol)
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SMILES for NP0047596 (8-Acetoxypinoresinol)
COC1=C(O)C=CC(=C1)C1OCC2(OC(C)=O)C1COC2C1=CC(OC)=C(O)C=C1
Download
INCHI for NP0047596 (8-Acetoxypinoresinol)
InChI=1S/C22H24O8/c1-12(23)30-22-11-29-20(13-4-6-16(24)18(8-13)26-2)15(22)10-28-21(22)14-5-7-17(25)19(9-14)27-3/h4-9,15,20-21,24-25H,10-11H2,1-3H3
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View in JSmol
Synonyms
ValueSource
1-AcetoxypinoresinolHMDB
1,4-Bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl acetic acidGenerator
Chemical FormulaC22H24O8
Average Mass416.4212 Da
Monoisotopic Mass416.14712 Da
IUPAC Name1,4-bis(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-3a-yl acetate
Traditional Name1,4-bis(4-hydroxy-3-methoxyphenyl)-tetrahydro-1H-furo[3,4-c]furan-3a-yl acetate
CAS Registry Number81426-14-4
SMILES
COC1=C(O)C=CC(=C1)C1OCC2(OC(C)=O)C1COC2C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C22H24O8/c1-12(23)30-22-11-29-20(13-4-6-16(24)18(8-13)26-2)15(22)10-28-21(22)14-5-7-17(25)19(9-14)27-3/h4-9,15,20-21,24-25H,10-11H2,1-3H3
InChI KeyNATDFORNCKZPCI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Olea europaeaFooDB
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.
KingdomOrganic compounds  
Super ClassLignans, neolignans and related compounds  
ClassFuranoid lignans  
Sub ClassNot Available
Direct ParentFuranoid lignans  
Alternative Parents
Substituents
  • Furanoid lignan
    • 

  • Furofuran lignan skeleton
    • 

  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Furofuran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.53ALOGPS
logP2.17ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.68 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.13 m³·mol⁻¹ChemAxon
Polarizability42.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0033280  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011303  
KNApSAcK IDC00002588  
Chemspider ID3682955  
KEGG Compound IDC10544  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4485133  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available