NP-MRD: Showing NP-Card for (9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one (NP0233792)

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Record Information

Version

2.0

Created at

2022-09-06 15:30:56 UTC

Updated at

2022-09-06 15:30:56 UTC

NP-MRD ID

NP0233792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one

Description

(13S)-4-(2,4-dihydroxyphenyl)-8,13-dihydroxy-12,12-dimethyl-5-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0²,⁷]Tetradeca-1(10),2(7),4,8-tetraen-6-one belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. (9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one is found in Morus nigra. Based on a literature review very few articles have been published on (13S)-4-(2,4-dihydroxyphenyl)-8,13-dihydroxy-12,12-dimethyl-5-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0²,⁷]Tetradeca-1(10),2(7),4,8-tetraen-6-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062217302D          

 32 35  0  0  1  0            999 V2000
   -2.5855   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3480   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3480   -2.7770    0.0000 O   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


  Mrv1652309062217302D          

 32 35  0  0  1  0            999 V2000
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   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0233792

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O7/c1-12(2)5-7-15-22(30)21-18(28)11-19-16(10-20(29)25(3,4)32-19)24(21)31-23(15)14-8-6-13(26)9-17(14)27/h5-6,8-9,11,20,26-29H,7,10H2,1-4H3/t20-/m0/s1

> <INCHI_KEY>
YKRQWKGDHFWDCR-FQEVSTJZSA-N

> <FORMULA>
C25H26O7

> <MOLECULAR_WEIGHT>
438.476

> <EXACT_MASS>
438.167853177

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.63500826665285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H,9H,10H-pyrano[2,3-h]chromen-4-one

> <JCHEM_LOGP>
4.266419224666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.258769637726262

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5327324576450945

> <JCHEM_PKA_STRONGEST_BASIC>
-3.338038151873209

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
121.26489999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9H,10H-pyrano[2,3-h]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-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      -4.826  -1.183   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.516  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.206  -6.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -7.851   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.206  -9.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.746  -9.185   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.516 -10.518   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.516  -7.851   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.746  -6.517   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.516  -5.184   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.104  -5.184   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -1.183   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.104   0.151   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.206  -1.183   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.724  -2.516   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.673  -2.860   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.673  -4.840   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.494  -6.517   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
CONECT   16    7   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23    6   25                                                  
CONECT   25   24                                                            
CONECT   26   19   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   18                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₇

Average Mass

438.4760 Da

Monoisotopic Mass

438.16785 Da

IUPAC Name

(9S)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H,9H,10H-pyrano[2,3-h]chromen-4-one

Traditional Name

(9S)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9H,10H-pyrano[2,3-h]chromen-4-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H26O7/c1-12(2)5-7-15-22(30)21-18(28)11-19-16(10-20(29)25(3,4)32-19)24(21)31-23(15)14-8-6-13(26)9-17(14)27/h5-6,8-9,11,20,26-29H,7,10H2,1-4H3/t20-/m0/s1

InChI Key

YKRQWKGDHFWDCR-FQEVSTJZSA-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 nigra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

8-prenylated flavones

Alternative Parents

Substituents

3-prenylated flavone
8-prenylated flavone
Pyranoflavonoid
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-benzopyran
Chromane
Benzopyran
Resorcinol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	4.27	ChemAxon
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	121.26 m³·mol⁻¹	ChemAxon
Polarizability	46.64 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

C00056986

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

46844472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one (NP0233792)

MOL for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

3D MOL for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

3D SDF for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

3D-SDF for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

PDB for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

3D PDB for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

SMILES for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

INCHI for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

Structure for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)

3D Structure for NP0233792 ((9s)-2-(2,4-dihydroxyphenyl)-5,9-dihydroxy-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-9h,10h-pyrano[2,3-h]chromen-4-one)