NP-MRD: Showing NP-Card for 5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one (NP0169214)

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Record Information

Version

2.0

Created at

2022-09-03 05:08:04 UTC

Updated at

2022-09-03 05:08:04 UTC

NP-MRD ID

NP0169214

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one

Description

8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-2H-furo[2,3-h]-1-benzopyran-2-one belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. Thus, 8,9-dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-2H-furo[2,3-H]-1-benzopyran-2-one is considered to be a flavonoid lipid molecule. 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-2H-furo[2,3-h]-1-benzopyran-2-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-2H-furo[2,3-h]-1-benzopyran-2-one has been detected, but not quantified in, fruits. 5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one is found in Mesua ferrea. This could make 8,9-dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-2H-furo[2,3-H]-1-benzopyran-2-one a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309392D          

 30 33  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061309392D          

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M  END
> <DATABASE_ID>
NP0169214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1=C2OC(CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O6/c1-12(2)20(26)19-21(27)18-14(13-8-6-5-7-9-13)11-17(25)30-22(18)15-10-16(24(3,4)28)29-23(15)19/h5-9,11-12,16,27-28H,10H2,1-4H3

> <INCHI_KEY>
KYQBNYMPQRSMLV-UHFFFAOYSA-N

> <FORMULA>
C24H24O6

> <MOLECULAR_WEIGHT>
408.4438

> <EXACT_MASS>
408.1572885

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
43.67240520112159

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-2H,8H,9H-furo[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
4.313196506999999

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.295915579656526

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.451511279109083

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1064568286522514

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
121.47869999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8H,9H-furo[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.619   6.054   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.731   7.315   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.791  -1.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.671  -2.040   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.237   6.198   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.698   6.150   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.048   4.889   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.970   4.793   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.320   3.532   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.748  -0.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.864   0.818   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.080   6.006   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.781   3.484   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.053   2.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.247   0.674   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.173   0.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.136  -0.539   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.514   2.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.163   3.340   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.648   4.649   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.703   3.388   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.786   0.722   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.565   1.983   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.482  -0.731   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.948  -1.848   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.187   4.601   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.431   4.745   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.294   0.578   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.060   1.616   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.597  -0.587   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   13                                                       
CONECT    9    7   13                                                       
CONECT   10   15   16                                                       
CONECT   11   14   17                                                       
CONECT   12    1    2   20                                                  
CONECT   13    8    9   14                                                  
CONECT   14   11   13   18                                                  
CONECT   15   10   22   23                                                  
CONECT   16   10   24   29                                                  
CONECT   17   11   25   30                                                  
CONECT   18   14   21   22                                                  
CONECT   19   20   21   23                                                  
CONECT   20   12   19   26                                                  
CONECT   21   18   19   27                                                  
CONECT   22   15   18   30                                                  
CONECT   23   15   19   29                                                  
CONECT   24    3    4   16   28                                             
CONECT   25   17                                                            
CONECT   26   20                                                            
CONECT   27   21                                                            
CONECT   28   24                                                            
CONECT   29   16   23                                                       
CONECT   30   17   22                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₄O₆

Average Mass

408.4438 Da

Monoisotopic Mass

408.15729 Da

IUPAC Name

5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-2H,8H,9H-furo[2,3-h]chromen-2-one

Traditional Name

5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8H,9H-furo[2,3-h]chromen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1=C2OC(CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O)C(C)(C)O

InChI Identifier

InChI=1S/C24H24O6/c1-12(2)20(26)19-21(27)18-14(13-8-6-5-7-9-13)11-17(25)30-22(18)15-10-16(24(3,4)28)29-23(15)19/h5-9,11-12,16,27-28H,10H2,1-4H3

InChI Key

KYQBNYMPQRSMLV-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
Mesua ferrea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
4-phenylcoumarin
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Coumaran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Lactone
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Neoflavonoids (LMPK12100015 )

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	3.74	ALOGPS
logP	4.31	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.48 m³·mol⁻¹	ChemAxon
Polarizability	43.67 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

HMDB0037241

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016252

KNApSAcK ID

Not Available

Chemspider ID

24843123

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one (NP0169214)

MOL for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

3D MOL for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

3D SDF for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

3D-SDF for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

PDB for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

3D PDB for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

SMILES for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

INCHI for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

Structure for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)

3D Structure for NP0169214 (5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one)