Showing NP-Card for 3,4-Dihydroxy-9-methoxypterocarpan (NP0335996)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-11 04:14:13 UTC
Updated at2024-09-11 04:14:13 UTC
NP-MRD IDNP0335996
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4-Dihydroxy-9-methoxypterocarpan
Description3,4-Dihydroxy-9-methoxypterocarpan belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. 3,4-Dihydroxy-9-methoxypterocarpan was first documented in 2005 (PMID: 15787450). Based on a literature review a small amount of articles have been published on 3,4-Dihydroxy-9-methoxypterocarpan (PMID: 16041657).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0335996 (3,4-Dihydroxy-9-methoxypterocarpan)

  Mrv2104 05262306462D          

 21 24  0  0  0  0            999 V2000
    7.2186    1.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521    1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    2.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289    1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    1.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762    1.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    0.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184    1.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    0.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246    2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14 12  2  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
Download

3D MOL for NP0335996 (3,4-Dihydroxy-9-methoxypterocarpan)

Download
3D SDF for NP0335996 (3,4-Dihydroxy-9-methoxypterocarpan)
  Mrv2104 05262306462D          

 21 24  0  0  0  0            999 V2000
    7.2186    1.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521    1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    2.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289    1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    1.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762    1.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    0.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184    1.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    0.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246    2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14 12  2  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2

> <INCHI_IDENTIFIER>
InChI=1/C16H14O5/c1-19-8-2-3-9-11-7-20-16-10(4-5-12(17)14(16)18)15(11)21-13(9)6-8/h2-6,11,15,17-18H,7H2,1H3

> <INCHI_KEY>
YRFDJOAWSXSLMG-UHFFFAOYNA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.17652178160036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6-diol

> <JCHEM_LOGP>
2.2056580746666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.96255721043192

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.464417062680505

> <JCHEM_PKA_STRONGEST_BASIC>
-4.412805737827614

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
75.04200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0335996 (3,4-Dihydroxy-9-methoxypterocarpan)
Download
PDB for NP0335996 (3,4-Dihydroxy-9-methoxypterocarpan)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      13.475   3.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.737   2.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.368   1.542   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.360   4.456   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.822   4.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.515   4.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.895   0.593   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.810   3.786   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.073   2.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.205   3.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.587   1.969   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.130   2.992   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.146   3.913   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.975   1.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.742   3.256   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.512   1.793   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.408   2.904   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.282   0.329   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.179   4.492   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.357   0.505   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.706   4.457   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    5   10                                                       
CONECT    5    4   12                                                       
CONECT    6    8   13                                                       
CONECT    7   11   20                                                       
CONECT    8    2    6   19                                                  
CONECT    9    3   11   13                                                  
CONECT   10    4   15   16                                                  
CONECT   11    7    9   15                                                  
CONECT   12    5   14   17                                                  
CONECT   13    6    9   21                                                  
CONECT   14   12   16   18                                                  
CONECT   15   10   11   21                                                  
CONECT   16   10   14   20                                                  
CONECT   17   12                                                            
CONECT   18   14                                                            
CONECT   19    1    8                                                       
CONECT   20    7   16                                                       
CONECT   21   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

Download
3D PDB for NP0335996 (3,4-Dihydroxy-9-methoxypterocarpan)
Download
SMILES for NP0335996 (3,4-Dihydroxy-9-methoxypterocarpan)
COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2
Download
INCHI for NP0335996 (3,4-Dihydroxy-9-methoxypterocarpan)
InChI=1/C16H14O5/c1-19-8-2-3-9-11-7-20-16-10(4-5-12(17)14(16)18)15(11)21-13(9)6-8/h2-6,11,15,17-18H,7H2,1H3
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC16H14O5
Average Mass286.2830 Da
Monoisotopic Mass286.08412 Da
IUPAC Name14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6-diol
Traditional Name14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6-diol
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2
InChI Identifier
InChI=1/C16H14O5/c1-19-8-2-3-9-11-7-20-16-10(4-5-12(17)14(16)18)15(11)21-13(9)6-8/h2-6,11,15,17-18H,7H2,1H3
InChI KeyYRFDJOAWSXSLMG-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the  6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassFuranoisoflavonoids  
Direct ParentPterocarpans  
Alternative Parents
Substituents
  • Isoflavanol
    • 

  • Pterocarpan
    • 

  • Isoflavan
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Benzofuran
    • 

  • Coumaran
    • 

  • Anisole
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP2.21ChemAxon
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.04 m³·mol⁻¹ChemAxon
Polarizability29.18 ųChemAxon
Number of Rings4ChemAxon
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 IDC00009615  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Falcao MJ, Pouliquem YB, Lima MA, Gramosa NV, Costa-Lotufo LV, Militao GC, Pessoa C, de Moraes MO, Silveira ER: Cytotoxic flavonoids from Platymiscium floribundum. J Nat Prod. 2005 Mar;68(3):423-6. doi: 10.1021/np049854d. [PubMed:15787450  ] 
  2. Militao GC, Jimenez PC, Wilke DV, Pessoa C, Falcao MJ, Sousa Lima MA, Silveira ER, de Moraes MO, Costa-Lotufo LV: Antimitotic properties of pterocarpans isolated from Platymiscium floribundum on sea urchin eggs. Planta Med. 2005 Jul;71(7):683-5. doi: 10.1055/s-2005-871277. [PubMed:16041657  ]