NP-MRD: Showing NP-Card for 7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione (NP0146199)

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Record Information

Version

2.0

Created at

2022-09-02 01:33:14 UTC

Updated at

2022-09-02 01:33:14 UTC

NP-MRD ID

NP0146199

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione

Description

7-(Hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxo-2,5-dihydrofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]Octane-2,6-dione belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione is found in Trichoderma citrinoviride. Based on a literature review very few articles have been published on 7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxo-2,5-dihydrofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]Octane-2,6-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203332D          

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M  END

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  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0146199

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CCCC(=O)C1C(C2C(=C(O)C=CC=CC)C(=O)C1(C)C(=O)C2(C)O)C1(C)OC(=O)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O8/c1-7-9-11-13-16(29)18-20-21(28(6)22(31)15(3)24(33)36-28)19(17(30)14-12-10-8-2)26(4,23(18)32)25(34)27(20,5)35/h7-11,13,19-21,29,31,35H,12,14H2,1-6H3

> <INCHI_KEY>
KCPUSSJDCHTZSH-UHFFFAOYSA-N

> <FORMULA>
C28H34O8

> <MOLECULAR_WEIGHT>
498.572

> <EXACT_MASS>
498.225368055

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.81500906810102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxo-2,5-dihydrofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
3.877609881333334

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.348524925694674

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.205829151554961

> <JCHEM_PKA_STRONGEST_BASIC>
-3.712823590140636

> <JCHEM_POLAR_SURFACE_AREA>
138.2

> <JCHEM_REFRACTIVITY>
138.75359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.778  -5.079   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.841  -3.858   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.314  -4.059   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.326  -2.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.673  -2.197   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.652  -0.519   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.400  -0.723   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.255  -0.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.027   1.824   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.897   2.066   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.523   2.262   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.747   3.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.758   1.342   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.319   1.879   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.578  -0.188   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.036  -1.798   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.201  -0.436   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.163  -0.797   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.538   0.193   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.042   0.558   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.126   2.504   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.165  -0.968   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.680  -1.243   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.602  -2.869   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.410   0.113   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.880   0.927   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.345   1.226   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.820   3.129   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.658   1.212   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.140   3.194   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.353   3.126   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.497   4.440   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.090   6.058   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.702   7.506   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.099   8.822   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.640  10.173   0.000  0.00  0.00           C+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   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   29                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15    8   19                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21   22   27                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27                                                            
CONECT   29   19   11   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   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

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC=CCCC(=O)C1C(C2C(=C(O)C=CC=CC)C(=O)C1(C)C(=O)C2(C)O)C1(C)OC(=O)C(C)=C1O

InChI Identifier

InChI=1S/C28H34O8/c1-7-9-11-13-16(29)18-20-21(28(6)22(31)15(3)24(33)36-28)19(17(30)14-12-10-8-2)26(4,23(18)32)25(34)27(20,5)35/h7-11,13,19-21,29,31,35H,12,14H2,1-6H3

InChI Key

KCPUSSJDCHTZSH-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
Trichoderma citrinoviride	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

Acyloin
2-furanone
Cyclic alcohol
Tertiary alcohol
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Enol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

76178390

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione (NP0146199)

MOL for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

3D MOL for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

3D SDF for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

3D-SDF for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

PDB for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

3D PDB for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

SMILES for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

INCHI for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

Structure for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)

3D Structure for NP0146199 (7-(hex-4-enoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione)