NP-MRD: Showing NP-Card for 2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one (NP0294766)

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Record Information

Version

2.0

Created at

2022-09-10 03:27:43 UTC

Updated at

2022-09-10 03:27:43 UTC

NP-MRD ID

NP0294766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

Description

CHEBI:4719 Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one is found in Hypericum drummondii. Based on a literature review very few articles have been published on CHEBI:4719.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102205272D          

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 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0294766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)C1=C(O)C(CC2=C(O)C3=C(OC(C)(C)C=C3)C(C(=O)CCC)=C2O)=C(O)C(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O8/c1-7-9-17(29)19-22(32)15(21(31)14-11-12-27(3,4)36-24(14)19)13-16-23(33)20(18(30)10-8-2)26(35)28(5,6)25(16)34/h11-12,31-34H,7-10,13H2,1-6H3

> <INCHI_KEY>
TYRGSQOBKQRXDI-UHFFFAOYSA-N

> <FORMULA>
C28H34O8

> <MOLECULAR_WEIGHT>
498.572

> <EXACT_MASS>
498.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.268793940049164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

> <JCHEM_LOGP>
5.411354701666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.18519367372413

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.692947729103847

> <JCHEM_PKA_STRONGEST_BASIC>
-4.680582046246692

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
139.13460000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-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       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.905  -4.326   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.528   0.677   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.518  -1.037   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.518  -6.663   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.528  -8.377   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   35                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   29                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   16   11   23                                                  
CONECT   23   22                                                            
CONECT   24   15   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   14                                                       
CONECT   30    9   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32    6   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₈

Average Mass

498.5720 Da

Monoisotopic Mass

498.22537 Da

IUPAC Name

2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

Traditional Name

2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

CCCC(=O)C1=C(O)C(CC2=C(O)C3=C(OC(C)(C)C=C3)C(C(=O)CCC)=C2O)=C(O)C(C)(C)C1=O

InChI Identifier

InChI=1S/C28H34O8/c1-7-9-17(29)19-22(32)15(21(31)14-11-12-27(3,4)36-24(14)19)13-16-23(33)20(18(30)10-8-2)26(35)28(5,6)25(16)34/h11-12,31-34H,7-10,13H2,1-6H3

InChI Key

TYRGSQOBKQRXDI-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
Hypericum drummondii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Butyrophenone
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Benzenoid
Vinylogous acid
Cyclic ketone
Ketone
Oxacycle
Ether
Enol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
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	5.41	ChemAxon
pKa (Strongest Acidic)	3.69	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139.13 m³·mol⁻¹	ChemAxon
Polarizability	53.27 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

390532

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441963

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one (NP0294766)

MOL for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

3D MOL for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

3D SDF for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

3D-SDF for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

PDB for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

3D PDB for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

SMILES for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

INCHI for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

Structure for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)

3D Structure for NP0294766 (2-butanoyl-4-[(8-butanoyl-5,7-dihydroxy-2,2-dimethylchromen-6-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one)