NP-MRD: Showing NP-Card for 3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one (NP0293759)

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Record Information

Version

2.0

Created at

2022-09-10 01:57:22 UTC

Updated at

2022-09-10 01:57:22 UTC

NP-MRD ID

NP0293759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one

Description

3-(2,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one belongs to the class of organic compounds known as furanochalcones. Furanochalcones are compounds containing a furan ring fused to either ring of a chalcone moiety. 3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one is found in Dorstenia barteri. Based on a literature review very few articles have been published on 3-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102203572D          

 30 33  0  0  0  0            999 V2000
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -0.4125    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6438   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1287   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9537   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9537   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9537   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -1.2375    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


  Mrv1652309102203572D          

 30 33  0  0  0  0            999 V2000
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0293759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CC2=C(O1)C=C(O)C(=C2)C(=O)C=CC1=CC=C2OC(C)(C)CCC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O5/c1-24(2)10-9-16-11-15(6-8-21(16)30-24)5-7-19(26)18-12-17-13-23(25(3,4)28)29-22(17)14-20(18)27/h5-8,11-12,14,23,27-28H,9-10,13H2,1-4H3

> <INCHI_KEY>
YSOHJTIJBIMQNH-UHFFFAOYSA-N

> <FORMULA>
C25H28O5

> <MOLECULAR_WEIGHT>
408.494

> <EXACT_MASS>
408.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.24734728348901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one

> <JCHEM_LOGP>
5.209731577666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.296596698399338

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.344072824711554

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106377326531957

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
117.081

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      16.135  -2.786   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.040  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.580  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.120  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.580  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.580  -0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.135  -0.294   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   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  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   30                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   21   15                                                       
CONECT   27    8   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    6   30                                                  
CONECT   30   29    2                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₅

Average Mass

408.4940 Da

Monoisotopic Mass

408.19367 Da

IUPAC Name

3-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one

Traditional Name

3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CC2=C(O1)C=C(O)C(=C2)C(=O)C=CC1=CC=C2OC(C)(C)CCC2=C1

InChI Identifier

InChI=1S/C25H28O5/c1-24(2)10-9-16-11-15(6-8-21(16)30-24)5-7-19(26)18-12-17-13-23(25(3,4)28)29-22(17)14-20(18)27/h5-8,11-12,14,23,27-28H,9-10,13H2,1-4H3

InChI Key

YSOHJTIJBIMQNH-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
Dorstenia barteri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanochalcones. Furanochalcones are compounds containing a furan ring fused to either ring of a chalcone moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Furanochalcones

Alternative Parents

Substituents

Furanochalcone
2'-hydroxychalcone
Cinnamic acid or derivatives
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Coumaran
Styrene
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Tertiary alcohol
Alpha,beta-unsaturated ketone
Ketone
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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	5.21	ChemAxon
pKa (Strongest Acidic)	7.34	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.08 m³·mol⁻¹	ChemAxon
Polarizability	46.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

85435244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one (NP0293759)

MOL for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

3D MOL for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

3D SDF for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

3D-SDF for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

PDB for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

3D PDB for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

SMILES for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

INCHI for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

Structure for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)

3D Structure for NP0293759 (3-(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)-1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one)