NP-MRD: Showing NP-Card for 3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one (NP0198379)

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Record Information

Version

2.0

Created at

2022-09-04 16:49:16 UTC

Updated at

2022-09-04 16:49:16 UTC

NP-MRD ID

NP0198379

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one

Description

3-{[(2R)-4,6-dihydroxy-5-[(2R)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one belongs to the class of organic compounds known as butyrophenones. Butyrophenones are compounds containing 1-phenylbutan-1-one moiety. 3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one is found in Helichrysum cephaloideum. Based on a literature review very few articles have been published on 3-{[(2R)-4,6-dihydroxy-5-[(2R)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218492D          

 32 34  0  0  1  0            999 V2000
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5517   -1.6805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2102   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
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  6  7  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042218492D          

 32 34  0  0  1  0            999 V2000
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0198379

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)C1=C(O)C(CC2=C(O)C(C)=C(CC)OC2=O)=C2O[C@H](CC2=C1O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O7/c1-7-12(5)20(26)19-22(28)14(24-15(23(19)29)10-18(31-24)11(3)4)9-16-21(27)13(6)17(8-2)32-25(16)30/h12,18,27-29H,3,7-10H2,1-2,4-6H3/t12-,18-/m1/s1

> <INCHI_KEY>
IWSMQZHOBSLDCV-KZULUSFZSA-N

> <FORMULA>
C25H30O7

> <MOLECULAR_WEIGHT>
442.508

> <EXACT_MASS>
442.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.09649227634107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2R)-4,6-dihydroxy-5-[(2R)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one

> <JCHEM_LOGP>
6.144091514666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.010533593175968

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.015531757182325

> <JCHEM_PKA_STRONGEST_BASIC>
-4.672774768980152

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
122.72069999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R)-4,6-dihydroxy-5-[(2R)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.496  -3.137   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.259  -7.463   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.592  -6.693   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.591  -7.463   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    9   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   20   30                                                  
CONECT   30   29                                                            
CONECT   31   18    6   32                                                  
CONECT   32   31    4                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₇

Average Mass

442.5080 Da

Monoisotopic Mass

442.19915 Da

IUPAC Name

3-{[(2R)-4,6-dihydroxy-5-[(2R)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one

Traditional Name

3-{[(2R)-4,6-dihydroxy-5-[(2R)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)C1=C(O)C(CC2=C(O)C(C)=C(CC)OC2=O)=C2O[C@H](CC2=C1O)C(C)=C

InChI Identifier

InChI=1S/C25H30O7/c1-7-12(5)20(26)19-22(28)14(24-15(23(19)29)10-18(31-24)11(3)4)9-16-21(27)13(6)17(8-2)32-25(16)30/h12,18,27-29H,3,7-10H2,1-2,4-6H3/t12-,18-/m1/s1

InChI Key

IWSMQZHOBSLDCV-KZULUSFZSA-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
Helichrysum cephaloideum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butyrophenones. Butyrophenones are compounds containing 1-phenylbutan-1-one moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Butyrophenones

Direct Parent

Butyrophenones

Alternative Parents

Substituents

Butyrophenone
Coumaran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Pyranone
Pyran
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Ether
Oxacycle
Organoheterocyclic compound
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	6.14	ChemAxon
pKa (Strongest Acidic)	7.02	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.72 m³·mol⁻¹	ChemAxon
Polarizability	47.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162929537

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one (NP0198379)

MOL for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

3D MOL for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

3D SDF for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

3D-SDF for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

PDB for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

3D PDB for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

SMILES for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

INCHI for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

Structure for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)

3D Structure for NP0198379 (3-{[(2r)-4,6-dihydroxy-5-[(2r)-2-methylbutanoyl]-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-6-ethyl-4-hydroxy-5-methylpyran-2-one)