NP-MRD: Showing NP-Card for (8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one (NP0284713)

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Record Information

Version

2.0

Created at

2022-09-09 12:33:09 UTC

Updated at

2022-09-09 12:33:09 UTC

NP-MRD ID

NP0284713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one

Description

(8S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methyl-4H,8H-pyrano[2,3-f]chromen-4-one belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position. (8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one is found in Morus alba. Based on a literature review very few articles have been published on (8S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methyl-4H,8H-pyrano[2,3-f]chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092214332D          

 33 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092214332D          

 33 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0284713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)=CCC1=C(OC2=C3C=C[C@@](C)(CO)OC3=CC(O)=C2C1=O)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O8/c1-13(11-26)3-5-17-22(31)21-19(30)10-20-16(7-8-25(2,12-27)33-20)24(21)32-23(17)15-6-4-14(28)9-18(15)29/h3-4,6-10,26-30H,5,11-12H2,1-2H3/t25-/m0/s1

> <INCHI_KEY>
KUZOHQFKZOINRC-VWLOTQADSA-N

> <FORMULA>
C25H24O8

> <MOLECULAR_WEIGHT>
452.459

> <EXACT_MASS>
452.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
47.221204214975245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methyl-4H,8H-pyrano[2,3-h]chromen-4-one

> <JCHEM_LOGP>
2.8903275116666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.237307010631756

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.45783853760432

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0472444551847113

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
124.18439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(8S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.826  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.056  -2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.516  -2.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206  -6.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564  -7.851   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.206  -9.185   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.746  -9.185   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.516 -10.518   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.516  -7.851   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.746  -6.517   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.516  -5.184   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.104  -5.184   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.183   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.104   0.151   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.206  -1.183   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.724  -2.516   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.673  -2.860   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.673  -4.840   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.121  -4.313   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.826  -1.183   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.366  -1.183   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16   23                                                  
CONECT   23   22    5   24                                                  
CONECT   24   23                                                            
CONECT   25   18   26                                                       
CONECT   26   25   27   28   30                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   26   31                                                       
CONECT   31   30   17                                                       
CONECT   32    2   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₈

Average Mass

452.4590 Da

Monoisotopic Mass

452.14712 Da

IUPAC Name

(8S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methyl-4H,8H-pyrano[2,3-h]chromen-4-one

Traditional Name

(8S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one

CAS Registry Number

Not Available

SMILES

CC(CO)=CCC1=C(OC2=C3C=C[C@@](C)(CO)OC3=CC(O)=C2C1=O)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C25H24O8/c1-13(11-26)3-5-17-22(31)21-19(30)10-20-16(7-8-25(2,12-27)33-20)24(21)32-23(17)15-6-4-14(28)9-18(15)29/h3-4,6-10,26-30H,5,11-12H2,1-2H3/t25-/m0/s1

InChI Key

KUZOHQFKZOINRC-VWLOTQADSA-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
Morus alba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

3-prenylated flavones

Alternative Parents

Substituents

3-prenylated flavone
Pyranoflavonoid
Hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Pyranochromene
Chromone
1-benzopyran
Benzopyran
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	2.89	ChemAxon
pKa (Strongest Acidic)	7.46	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.18 m³·mol⁻¹	ChemAxon
Polarizability	47.22 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

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

162869315

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one (NP0284713)

MOL for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

3D MOL for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

3D SDF for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

3D-SDF for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

PDB for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

3D PDB for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

SMILES for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

INCHI for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

Structure for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)

3D Structure for NP0284713 ((8s)-2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl)-8-(hydroxymethyl)-8-methylpyrano[2,3-h]chromen-4-one)