NP-MRD: Showing NP-Card for 3,9-dihydroxypterocarpan (NP0233799)

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Record Information

Version

2.0

Created at

2022-09-06 15:31:48 UTC

Updated at

2022-09-06 15:31:48 UTC

NP-MRD ID

NP0233799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,9-dihydroxypterocarpan

Description

(6AR,11aR)-3,9-dihydroxypterocarpan 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 (6aR,11aR)-3,9-dihydroxypterocarpan is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 3,9-dihydroxypterocarpan is found in Amorpha fruticosa, Arachis hypogaea, Calopogonium mucunoides, Erythrina abyssinica, Erythrina fusca, Erythrina poeppigiana and Phaseolus vulgaris. Based on a literature review very few articles have been published on (6aR,11aR)-3,9-dihydroxypterocarpan.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -5.2128    1.5555   -1.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0791    0.8719   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2125   -0.2285    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1410   -0.9544    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8701   -0.5729    0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7286    0.5114   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187    1.2624   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3630    0.7050   -0.9827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3016   -0.5466   -0.7205 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6979   -0.2709   -0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7124   -0.4854   -1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9974   -0.1978   -0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042    0.2827    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5962    0.5748    0.7601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620    0.4830    1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9752    0.2115    0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681    0.3798    1.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.6337    1.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5122   -1.1040    0.3903 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1062    2.3507   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1970   -0.5513    0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051   -1.8149    1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678    2.1229   -1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1905   -1.2145   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694   -0.8651   -2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -0.3523   -1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9045    1.5404    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559    0.8635    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9892   -0.2027    2.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2298   -1.5113    2.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340   -2.2091    0.3041 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 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  7  2  1  0
  6  5  1  0
  9 19  1  0
 10 16  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
 19 31  1  1
 18 29  1  0
 18 30  1  0
 15 28  1  0
 14 27  1  0
 12 26  1  0
 11 25  1  0
  9 24  1  6
  7 23  1  0
M  END


  Mrv1652309062217322D          

 19 22  0  0  1  0            999 V2000
   -0.5447   -2.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 C   0  0  1  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19  5  1  1  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2[C@@H]3COC4=CC(O)=CC=C4[C@@H]3OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c16-8-2-4-11-13(5-8)18-7-12-10-3-1-9(17)6-14(10)19-15(11)12/h1-6,12,15-17H,7H2/t12-,15-/m0/s1

> <INCHI_KEY>
ODMIEGVTNZNSLD-WFASDCNBSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.257

> <EXACT_MASS>
256.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.1947452687669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10R)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaene-5,14-diol

> <JCHEM_LOGP>
2.3633293403333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.792877417503597

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.180799963142011

> <JCHEM_PKA_STRONGEST_BASIC>
-4.587232188183343

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
68.57880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10R)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.017  -4.582   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.352  -5.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.425  -6.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.794  -7.531   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.090  -6.699   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.016  -5.161   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.648  -4.455   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.457  -4.616   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.420  -5.817   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.958  -5.905   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803  -4.618   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.340  -4.706   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.033  -6.081   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.570  -6.169   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.188  -7.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.650  -7.281   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.805  -8.568   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.268  -8.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.575  -7.105   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    5    9                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
(6AR-cis)-6a,11a-dihydro-6H-benzofuro(3,2-c)(1)benzopyran-3,9-diol	ChEBI

Chemical Formula

C₁₅H₁₂O₄

Average Mass

256.2570 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC=C2[C@@H]3COC4=CC(O)=CC=C4[C@@H]3OC2=C1

InChI Identifier

InChI=1S/C15H12O4/c16-8-2-4-11-13(5-8)18-7-12-10-3-1-9(17)6-14(10)19-15(11)12/h1-6,12,15-17H,7H2/t12-,15-/m0/s1

InChI Key

ODMIEGVTNZNSLD-WFASDCNBSA-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
Amorpha fruticosa	LOTUS Database	35616633
Arachis hypogaea	LOTUS Database	35616633
Calopogonium mucunoides	LOTUS Database	35616633
Erythrina abyssinica	LOTUS Database	35616633
Erythrina fusca	LOTUS Database	35616633
Erythrina poeppigiana	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Benzofuran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterocarpans (CHEBI:15648 )
Pterocarpanes (C04271 )

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

C00009610

Chemspider ID

143036

KEGG Compound ID

C04271

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162933

PDB ID

Not Available

ChEBI ID

15648

Good Scents ID

rw1865801

References

General References

LOTUS database [Link]

Showing NP-Card for 3,9-dihydroxypterocarpan (NP0233799)

MOL for NP0233799 (3,9-dihydroxypterocarpan)

3D MOL for NP0233799 (3,9-dihydroxypterocarpan)

3D SDF for NP0233799 (3,9-dihydroxypterocarpan)

3D-SDF for NP0233799 (3,9-dihydroxypterocarpan)

PDB for NP0233799 (3,9-dihydroxypterocarpan)

3D PDB for NP0233799 (3,9-dihydroxypterocarpan)

SMILES for NP0233799 (3,9-dihydroxypterocarpan)

INCHI for NP0233799 (3,9-dihydroxypterocarpan)

Structure for NP0233799 (3,9-dihydroxypterocarpan)

3D Structure for NP0233799 (3,9-dihydroxypterocarpan)