NP-MRD: Showing NP-Card for 3-Hydroxy-8,9-methylenedioxypterocarpene (NP0138400)

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Record Information

Version

1.0

Created at

2022-05-31 17:57:49 UTC

Updated at

2022-05-31 17:57:49 UTC

NP-MRD ID

NP0138400

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Hydroxy-8,9-methylenedioxypterocarpene

Description

5,7,11,19-Tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]Icosa-1(12),2,4(8),9,13(18),14,16-heptaen-16-ol 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. Thus, 5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]Icosa-1(12),2,4(8),9,13(18),14,16-heptaen-16-ol is considered to be a flavonoid lipid molecule. 5,7,11,19-Tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]Icosa-1(12),2,4(8),9,13(18),14,16-heptaen-16-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 35  0  0  0  0  0  0  0  0999 V2000
    6.2704   -0.4976   -0.1106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8858   -0.4670   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -1.2410   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8515   -1.1787   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311   -0.3970   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732    0.3822    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    0.3210    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0817    1.1612    1.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7050    1.3083    1.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    0.4767    0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6743   -0.3228   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -0.9540   -1.0032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054   -0.6028   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6688   -0.9368   -1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8285   -0.4182   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7322    0.4689    0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4917    0.8212    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3293    0.2922    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0054    0.8545    0.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9702    0.2295   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1998   -0.5897   -0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8053    0.0434    0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7925   -1.8605   -1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3139   -1.7790   -1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736    0.9349    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766    1.0242    2.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3886    2.3951    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166   -1.6434   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3559    1.5207    1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5369    0.9945   -0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7251   -0.3402    0.5699 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 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
 10 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 21  1  0
 21 20  1  0
 20 19  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
  7  2  1  0
 13 18  1  0
  6  5  1  0
 19 16  1  0
 12 11  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  9 26  1  0
  9 27  1  0
  7 25  1  0
 17 29  1  0
 20 30  1  0
 20 31  1  0
 14 28  1  0
M  END


  Mrv1533004241518112D          

 21 25  0  0  0  0            999 V2000
    6.6296    1.6377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8066    1.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4448    0.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218    0.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1606    1.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5224    2.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0612    2.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2382    2.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764    2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3376    1.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8295    0.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543    1.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3258    0.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263    1.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668    0.8635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280    1.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1199    2.1976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6553    1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    2.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0833    1.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3454    2.2644    0.0000 C   0  0  0  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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  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
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 20  1  0  0  0  0
 12 20  1  0  0  0  0
  6 21  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138400

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C3=C(COC2=C1)C1=CC2=C(OCO2)C=C1O3

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,17H,6-7H2

> <INCHI_KEY>
XCDMHEXDCIXKLK-UHFFFAOYSA-N

> <FORMULA>
C16H10O5

> <MOLECULAR_WEIGHT>
282.251

> <EXACT_MASS>
282.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
28.965959390088393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13,15,17-heptaen-16-ol

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
2.6128198840000003

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.953937737052323

> <JCHEM_PKA_STRONGEST_BASIC>
-2.878705370585157

> <JCHEM_POLAR_SURFACE_AREA>
61.06

> <JCHEM_REFRACTIVITY>
72.6784

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13,15,17-heptaen-16-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0      12.375   3.057   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.839   2.950   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.164   1.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.627   1.459   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.766   2.736   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.442   4.120   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.581   5.397   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.045   5.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.369   3.906   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.230   2.629   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.282   1.415   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.835   1.942   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.475   1.220   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.169   2.036   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.311   1.612   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.172   2.889   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.224   4.102   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.223   3.575   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.583   4.298   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.889   3.481   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.978   4.227   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    9   12                                                  
CONECT   21    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₀O₅

Average Mass

282.2510 Da

Monoisotopic Mass

282.05282 Da

IUPAC Name

5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13,15,17-heptaen-16-ol

Traditional Name

5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13,15,17-heptaen-16-ol

CAS Registry Number

59901-98-3

SMILES

OC1=CC=C2C3=C(COC2=C1)C1=CC2=C(OCO2)C=C1O3

InChI Identifier

InChI=1S/C16H10O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,17H,6-7H2

InChI Key

XCDMHEXDCIXKLK-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Pterocarpan
Benzopyran
1-benzopyran
Benzodioxole
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Furan
Heteroaromatic compound
Organoheterocyclic compound
Ether
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070159 )

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	2.87	ALOGPS
logP	2.61	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.68 m³·mol⁻¹	ChemAxon
Polarizability	28.97 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Hydroxy-8,9-methylenedioxypterocarpene (NP0138400)

MOL for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

3D MOL for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

3D SDF for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

3D-SDF for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

PDB for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

3D PDB for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

SMILES for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

INCHI for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

Structure for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)

3D Structure for NP0138400 (3-Hydroxy-8,9-methylenedioxypterocarpene)