NP-MRD: Showing NP-Card for (2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one (NP0151293)

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Record Information

Version

2.0

Created at

2022-09-02 07:35:09 UTC

Updated at

2022-09-02 07:35:10 UTC

NP-MRD ID

NP0151293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one

Description

3-(2,4-Dihydroxyphenyl)-1-[(3R)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-6-yl]prop-2-en-1-one belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. (2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one is found in Sophora flavescens. Based on a literature review very few articles have been published on 3-(2,4-dihydroxyphenyl)-1-[(3R)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-6-yl]prop-2-en-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022209352D          

 32 34  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -0.0000    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


  Mrv1652309022209352D          

 32 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0151293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C[C@@H](CC=C(C)C)C(C)(C)O2)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O6/c1-15(2)6-9-17-12-19-22(32-26(17,3)4)14-23(31-5)24(25(19)30)20(28)11-8-16-7-10-18(27)13-21(16)29/h6-8,10-11,13-14,17,27,29-30H,9,12H2,1-5H3/b11-8+/t17-/m1/s1

> <INCHI_KEY>
JJMWPCIGAITBBF-VGMNTSGFSA-N

> <FORMULA>
C26H30O6

> <MOLECULAR_WEIGHT>
438.52

> <EXACT_MASS>
438.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
48.415589011602776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(2,4-dihydroxyphenyl)-1-[(3R)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-6-yl]prop-2-en-1-one

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
6.076014113333333

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.701451502743394

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.437519488741929

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5936985356332505

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
126.3869

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(2,4-dihydroxyphenyl)-1-[(3R)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.518  -2.043   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.528  -3.757   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20                                                            
CONECT   22    6   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29    5                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₆

Average Mass

438.5200 Da

Monoisotopic Mass

438.20424 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C[C@@H](CC=C(C)C)C(C)(C)O2)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C26H30O6/c1-15(2)6-9-17-12-19-22(32-26(17,3)4)14-23(31-5)24(25(19)30)20(28)11-8-16-7-10-18(27)13-21(16)29/h6-8,10-11,13-14,17,27,29-30H,9,12H2,1-5H3/b11-8+/t17-/m1/s1

InChI Key

JJMWPCIGAITBBF-VGMNTSGFSA-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
Sophora flavescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Hydroxycinnamic acid or derivatives
2,2-dimethyl-1-benzopyran
Aromatic monoterpenoid
Chromane
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
1-benzopyran
Anisole
Resorcinol
Styrene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Vinylogous acid
Acryloyl-group
Enone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	4.95	ALOGPS
logS	-5.3	ALOGPS

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

163193946

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one (NP0151293)

MOL for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

3D MOL for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

3D SDF for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

3D-SDF for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

PDB for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

3D PDB for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

SMILES for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

INCHI for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

Structure for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)

3D Structure for NP0151293 ((2e)-3-(2,4-dihydroxyphenyl)-1-[(3r)-5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-en-1-yl)-3,4-dihydro-1-benzopyran-6-yl]prop-2-en-1-one)