NP-MRD: Showing NP-Card for (Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one (NP0051391)

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Record Information

Version

2.0

Created at

2022-04-27 22:46:36 UTC

Updated at

2022-04-27 22:46:36 UTC

NP-MRD ID

NP0051391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one

Description

4,5-Methylenedioxy-6-hydroxyaurone, also known as cephalocerone, belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). Thus, 4,5-methylenedioxy-6-hydroxyaurone is considered to be a flavonoid. 4,5-Methylenedioxy-6-hydroxyaurone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one is found in Cephalocereus senilis. Based on a literature review very few articles have been published on 4,5-methylenedioxy-6-hydroxyaurone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
    1.0950   -1.8863   -1.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8173   -1.0250   -1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4882   -0.5199   -0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6380   -0.9037   -1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798   -0.3214   -0.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0076   -1.1072   -0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296   -0.6235   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3225    0.6781    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2149    1.4991    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    0.9864   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2829    0.3806    0.2978 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0852    0.4857    0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8041    1.2306    1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1935    1.1435    1.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306    1.8853    2.5170 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8761    0.2922    0.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -0.4501   -0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038   -0.3604   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0411   -1.2510   -0.9019 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2629   -1.2693   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2330   -0.0399    0.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -1.6386   -2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9728   -2.1412   -1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0835   -1.2599   -0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2961    1.0398    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3150    2.5075    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1412    1.6481   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3139    1.9103    2.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4695    2.5164    3.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1511   -1.2577   -0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2076   -2.1486    0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 18  2  0
 18  2  1  0
  2  1  2  0
  2  3  1  0
  3 11  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 18 17  1  0
 17 16  2  0
 16 21  1  0
 21 20  1  0
 20 19  1  0
 16 14  1  0
 11 12  1  0
 10  5  1  0
 19 17  1  0
 15 29  1  0
 13 28  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 20 30  1  0
 20 31  1  0
M  END


  Mrv1652304282200462D          

 21 24  0  0  0  0            999 V2000
    3.5196    0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    1.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -0.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5398    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6832    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6832   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9688   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717    1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    1.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  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
  5  9  1  0  0  0  0
  4 10  1  0  0  0  0
  2 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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 12 20  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C(=O)\C(O2)=C\C2=CC=CC=C2)C2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O5/c17-10-7-11-13(16-15(10)19-8-20-16)14(18)12(21-11)6-9-4-2-1-3-5-9/h1-7,17H,8H2/b12-6-

> <INCHI_KEY>
KLYHONUCJQKOKE-SDQBBNPISA-N

> <FORMULA>
C16H10O5

> <MOLECULAR_WEIGHT>
282.251

> <EXACT_MASS>
282.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
28.66389227562511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11Z)-7-hydroxy-11-(phenylmethylidene)-3,5,10-trioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-12-one

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
2.5219424623333335

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.083219206341102

> <JCHEM_PKA_STRONGEST_BASIC>
-4.723758554050431

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
74.79410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11Z)-7-hydroxy-11-(phenylmethylidene)-3,5,10-trioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.570   0.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.340  -0.427   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.570  -1.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.030  -1.760   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.260  -0.427   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.030   0.907   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.000   2.051   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.593   1.425   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.754  -0.107   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.260  -3.094   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.846  -0.107   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.007   1.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.341   2.195   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.675   1.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.008   2.195   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.342   1.425   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.342  -0.115   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.008  -0.885   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.675  -0.115   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.600   2.051   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.280   3.558   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    4                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   12    1   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
Cephalocerone	ChEBI

Chemical Formula

C₁₆H₁₀O₅

Average Mass

282.2510 Da

Monoisotopic Mass

282.05282 Da

IUPAC Name

(11Z)-7-hydroxy-11-(phenylmethylidene)-3,5,10-trioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-12-one

Traditional Name

(11Z)-7-hydroxy-11-(phenylmethylidene)-3,5,10-trioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-12-one

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C(=O)\C(O2)=C\C2=CC=CC=C2)C2=C1OCO2

InChI Identifier

InChI=1S/C16H10O5/c17-10-7-11-13(16-15(10)19-8-20-16)14(18)12(21-11)6-9-4-2-1-3-5-9/h1-7,17H,8H2/b12-6-

InChI Key

KLYHONUCJQKOKE-SDQBBNPISA-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

Species Name	Source	Reference
Cephalocereus senilis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Benzodioxole
Coumaran
Benzofuran
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyaurone (CHEBI:1749 )
aurones (C08722 )
Aurone flavonoids (LMPK12130053 )

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	2.52	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.08	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.79 m³·mol⁻¹	ChemAxon
Polarizability	28.66 Å³	ChemAxon
Number of Rings	4	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

C00002385

Chemspider ID

4444679

KEGG Compound ID

C08722

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281293

PDB ID

Not Available

ChEBI ID

1749

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one (NP0051391)

MOL for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

3D MOL for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

3D SDF for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

3D-SDF for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

PDB for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

3D PDB for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

SMILES for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

INCHI for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

Structure for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)

3D Structure for NP0051391 ((Z)-4-Hydroxy-7-(phenylmethylene)-furo[3,2-e]-1,3-benzodioxol-8(7H)-one)