NP-MRD: Showing NP-Card for 6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol (NP0227336)

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Record Information

Version

2.0

Created at

2022-09-06 06:37:51 UTC

Updated at

2022-09-06 06:37:51 UTC

NP-MRD ID

NP0227336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol

Description

CHEMBL4066416 belongs to the class of organic compounds known as 2'-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 2'-position. 6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol is found in Broussonetia papyrifera. Based on a literature review very few articles have been published on CHEMBL4066416.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062208372D          

 29 32  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -2.8875    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


  Mrv1652309062208372D          

 29 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0227336

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(C=C2C=CC(C)(C)OC2=C1O)[C@H]1CCC2=CC=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O4/c1-15(2)5-9-19-20(13-17-11-12-25(3,4)29-24(17)23(19)27)21-10-7-16-6-8-18(26)14-22(16)28-21/h5-6,8,11-14,21,26-27H,7,9-10H2,1-4H3/t21-/m1/s1

> <INCHI_KEY>
QSCBHDIGHKHWKC-OAQYLSRUSA-N

> <FORMULA>
C25H28O4

> <MOLECULAR_WEIGHT>
392.495

> <EXACT_MASS>
392.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.89805141373029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(2R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-2H-chromen-8-ol

> <JCHEM_LOGP>
6.106331666999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.995627105582843

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.3352415781637

> <JCHEM_PKA_STRONGEST_BASIC>
-4.627678141724556

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
117.3126

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol

> <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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.196  -1.633   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.186  -3.347   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -5.390   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   22                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17    8                                                       
CONECT   19    7   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21    6   23                                                  
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   20                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₄

Average Mass

392.4950 Da

Monoisotopic Mass

392.19876 Da

IUPAC Name

6-[(2R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-2H-chromen-8-ol

Traditional Name

6-[(2R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(C=C2C=CC(C)(C)OC2=C1O)[C@H]1CCC2=CC=C(O)C=C2O1

InChI Identifier

InChI=1S/C25H28O4/c1-15(2)5-9-19-20(13-17-11-12-25(3,4)29-24(17)23(19)27)21-10-7-16-6-8-18(26)14-22(16)28-21/h5-6,8,11-14,21,26-27H,7,9-10H2,1-4H3/t21-/m1/s1

InChI Key

QSCBHDIGHKHWKC-OAQYLSRUSA-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
Broussonetia papyrifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

2'-prenylated flavans

Alternative Parents

Substituents

Pyranoflavonoid
2'-prenylated flavan
3'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	6.11	ChemAxon
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	117.31 m³·mol⁻¹	ChemAxon
Polarizability	44.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

76783397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

137631532

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol (NP0227336)

MOL for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

3D MOL for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

3D SDF for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

3D-SDF for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

PDB for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

3D PDB for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

SMILES for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

INCHI for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

Structure for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)

3D Structure for NP0227336 (6-[(2r)-7-hydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)chromen-8-ol)