NP-MRD: Showing NP-Card for 3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one (NP0219192)

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Record Information

Version

2.0

Created at

2022-09-05 20:06:32 UTC

Updated at

2022-09-05 20:06:32 UTC

NP-MRD ID

NP0219192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one

Description

CHEMBL2334821 belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one is found in Helichrysum italicum. Based on a literature review very few articles have been published on CHEMBL2334821.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222062D          

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 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)C(C1=C(O)C(CC)=C(C)OC1=O)C1=C(O)C(CC=C(C)C)=C(O)C(C(C)=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O8/c1-7-9-10-11-19(30)21(23-24(31)17(8-2)16(6)36-28(23)35)22-26(33)18(13-12-14(3)4)25(32)20(15(5)29)27(22)34/h12,21,31-34H,7-11,13H2,1-6H3

> <INCHI_KEY>
MLHCHYFNKPHMMY-UHFFFAOYSA-N

> <FORMULA>
C28H36O8

> <MOLECULAR_WEIGHT>
500.588

> <EXACT_MASS>
500.241018119

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.00503189652299

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methyl-2H-pyran-2-one

> <JCHEM_LOGP>
6.473065144333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.65192082254701

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.776540783225785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.661194378046891

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
140.5522

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.908  -5.684   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20    9   25                                                  
CONECT   25   24                                                            
CONECT   26    8   27   35                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   26   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₈

Average Mass

500.5880 Da

Monoisotopic Mass

500.24102 Da

IUPAC Name

3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methyl-2H-pyran-2-one

Traditional Name

3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)C(C1=C(O)C(CC)=C(C)OC1=O)C1=C(O)C(CC=C(C)C)=C(O)C(C(C)=O)=C1O

InChI Identifier

InChI=1S/C28H36O8/c1-7-9-10-11-19(30)21(23-24(31)17(8-2)16(6)36-28(23)35)22-26(33)18(13-12-14(3)4)25(32)20(15(5)29)27(22)34/h12,21,31-34H,7-11,13H2,1-6H3

InChI Key

MLHCHYFNKPHMMY-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
Helichrysum italicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acylphloroglucinol derivative
Acetophenone
Benzenetriol
Phloroglucinol derivative
Benzoyl
Aryl alkyl ketone
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	6.47	ChemAxon
pKa (Strongest Acidic)	6.78	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	140.55 m³·mol⁻¹	ChemAxon
Polarizability	54.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

29419114

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71717009

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one (NP0219192)

MOL for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

3D MOL for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

3D SDF for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

3D-SDF for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

PDB for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

3D PDB for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

SMILES for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

INCHI for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

Structure for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)

3D Structure for NP0219192 (3-{1-[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-2-oxoheptyl}-5-ethyl-4-hydroxy-6-methylpyran-2-one)