NP-MRD: Showing NP-Card for 3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one (NP0197776)

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Record Information

Version

2.0

Created at

2022-09-04 16:06:04 UTC

Updated at

2022-09-04 16:06:04 UTC

NP-MRD ID

NP0197776

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one

Description

MCULE-6234375391 belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position. 3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one is found in Erythrina addisoniae. Based on a literature review very few articles have been published on MCULE-6234375391.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218062D          

 31 34  0  0  0  0            999 V2000
    0.3020   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7425    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042218062D          

 31 34  0  0  0  0            999 V2000
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   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0197776

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OCC(C2=O)C2=CC=C(O)C=C2O)C2=C1OC(C)(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O6/c1-13(2)5-7-16-21(28)20-22(29)18(15-8-6-14(26)11-19(15)27)12-30-24(20)17-9-10-25(3,4)31-23(16)17/h5-6,8-11,18,26-28H,7,12H2,1-4H3

> <INCHI_KEY>
JFNOODAWRZYNPU-UHFFFAOYSA-N

> <FORMULA>
C25H26O6

> <MOLECULAR_WEIGHT>
422.477

> <EXACT_MASS>
422.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.76467454812969

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2,4-dihydroxyphenyl)-8-hydroxy-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

> <JCHEM_LOGP>
5.356848515333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.227592566726129

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.549284683209265

> <JCHEM_PKA_STRONGEST_BASIC>
-4.638127726537323

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
120.31269999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-(2,4-dihydroxyphenyl)-8-hydroxy-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.564  -5.898   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.386  -0.220   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.386   1.760   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.034  -1.897   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.494  -1.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   11                                                       
CONECT   19   10   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28                                                            
CONECT   30   21    9   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₆

Average Mass

422.4770 Da

Monoisotopic Mass

422.17294 Da

IUPAC Name

5-(2,4-dihydroxyphenyl)-8-hydroxy-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

Traditional Name

5-(2,4-dihydroxyphenyl)-8-hydroxy-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(OCC(C2=O)C2=CC=C(O)C=C2O)C2=C1OC(C)(C)C=C2

InChI Identifier

InChI=1S/C25H26O6/c1-13(2)5-7-16-21(28)20-22(29)18(15-8-6-14(26)11-19(15)27)12-30-24(20)17-9-10-25(3,4)31-23(16)17/h5-6,8-11,18,26-28H,7,12H2,1-4H3

InChI Key

JFNOODAWRZYNPU-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, 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
Erythrina addisoniae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

8-prenylated isoflavanones

Alternative Parents

Substituents

8-prenylated isoflavanone
Pyranoisoflavonoid
Isoflavanol
Hydroxyisoflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Resorcinol
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	5.36	ChemAxon
pKa (Strongest Acidic)	8.55	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	120.31 m³·mol⁻¹	ChemAxon
Polarizability	45.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

10138589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11964495

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one (NP0197776)

MOL for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

3D MOL for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

3D SDF for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

3D-SDF for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

PDB for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

3D PDB for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

SMILES for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

INCHI for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

Structure for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)

3D Structure for NP0197776 (3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-f]chromen-4-one)