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Showing NP-Card for Taiwanin E (NP0050484)

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Record Information
Version2.0
Created at2022-04-27 21:45:25 UTC
Updated at2022-04-27 21:45:25 UTC
NP-MRD IDNP0050484
Secondary Accession NumbersNone
Natural Product Identification
Common NameTaiwanin E
Description10-(2H-1,3-benzodioxol-5-yl)-16-hydroxy-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8,10,15-pentaen-12-one belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities. Taiwanin E is found in Chamaecyparis formosensis, Chamaecyparis obtusa, Cleistanthus collinus, Justicia patentiflora, Justicia procumbens and Taiwania cryptomerioides. 10-(2H-1,3-benzodioxol-5-yl)-16-hydroxy-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8,10,15-pentaen-12-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050484 (Taiwanin E)


  Mrv1533004171516002D          

 27 32  0  0  0  0            999 V2000
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -0.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238    2.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3443    2.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6799    1.5041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  3  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
  9 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
  2 27  2  0  0  0  0
 19 27  1  0  0  0  0
M  END
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3D MOL for NP0050484 (Taiwanin E)

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3D SDF for NP0050484 (Taiwanin E)

  Mrv1533004171516002D          

 27 32  0  0  0  0            999 V2000
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -0.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5238    2.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3443    2.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6799    1.5041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  3  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
  9 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
  2 27  2  0  0  0  0
 19 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C2C=C3OCOC3=CC2=C(C2=C1COC2=O)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O7/c21-19-11-5-16-15(26-8-27-16)4-10(11)17(18-12(19)6-23-20(18)22)9-1-2-13-14(3-9)25-7-24-13/h1-5,21H,6-8H2

> <INCHI_KEY>
YYFMUDJSHVYJGD-UHFFFAOYSA-N

> <FORMULA>
C20H12O7

> <MOLECULAR_WEIGHT>
364.309

> <EXACT_MASS>
364.058302726

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
35.83652325732504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-(2H-1,3-benzodioxol-5-yl)-16-hydroxy-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
3.1075538136666667

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.819235716785094

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.041763714371031

> <JCHEM_PKA_STRONGEST_BASIC>
-4.442943278494371

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
91.739

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-(2H-1,3-benzodioxol-5-yl)-16-hydroxy-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050484 (Taiwanin E)
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PDB for NP0050484 (Taiwanin E)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.983  -0.902   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.578   4.054   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.109   4.214   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.736   2.808   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    3    9                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   10                                                       
CONECT   19    9   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26    2   19                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

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3D PDB for NP0050484 (Taiwanin E)
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SMILES for NP0050484 (Taiwanin E)
OC1=C2C=C3OCOC3=CC2=C(C2=C1COC2=O)C1=CC=C2OCOC2=C1
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INCHI for NP0050484 (Taiwanin E)
InChI=1S/C20H12O7/c21-19-11-5-16-15(26-8-27-16)4-10(11)17(18-12(19)6-23-20(18)22)9-1-2-13-14(3-9)25-7-24-13/h1-5,21H,6-8H2
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SynonymsNot Available
Chemical FormulaC20H12O7
Average Mass364.3090 Da
Monoisotopic Mass364.05830 Da
IUPAC Name10-(2H-1,3-benzodioxol-5-yl)-16-hydroxy-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one
Traditional Name10-(2H-1,3-benzodioxol-5-yl)-16-hydroxy-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one
CAS Registry NumberNot Available
SMILES
OC1=C2C=C3OCOC3=CC2=C(C2=C1COC2=O)C1=CC=C2OCOC2=C1
InChI Identifier
InChI=1S/C20H12O7/c21-19-11-5-16-15(26-8-27-16)4-10(11)17(18-12(19)6-23-20(18)22)9-1-2-13-14(3-9)25-7-24-13/h1-5,21H,6-8H2
InChI KeyYYFMUDJSHVYJGD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Chamaecyparis formosensisPlant
Chamaecyparis obtusaPlant
Cleistanthus collinusLOTUS Database
Justicia patentifloraLOTUS Database
Justicia procumbensPlant
Taiwania cryptomerioidesPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.
KingdomOrganic compounds  
Super ClassLignans, neolignans and related compounds  
ClassArylnaphthalene lignans  
Sub ClassNot Available
Direct ParentArylnaphthalene lignans  
Alternative Parents
Substituents
  • Arylnaphthalene lignan skeleton
    • 

  • Lignan lactone
    • 

  • Linear furanonaphthodioxole
    • 

  • Naphthofuran
    • 

  • 1-naphthol
    • 

  • Isobenzofuranone
    • 

  • Naphthalene
    • 

  • Phthalide
    • 

  • Benzodioxole
    • 

  • Isocoumaran
    • 

  • Benzenoid
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Acetal
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen 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
logP2.68ALOGPS
logP3.11ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.04ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.74 m³·mol⁻¹ChemAxon
Polarizability35.84 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound493164  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available