NP-MRD: Showing NP-Card for 3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione (NP0224195)

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Record Information

Version

2.0

Created at

2022-09-06 02:29:47 UTC

Updated at

2022-09-06 02:29:47 UTC

NP-MRD ID

NP0224195

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione

Description

3-(4-Hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. 3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione is found in Jackrogersella minutella. Based on a literature review very few articles have been published on 3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062204292D          

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M  END

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  Mrv1652309062204292D          

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M  END
> <DATABASE_ID>
NP0224195

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)C1=C2C3=COC(=CC3=CC(=O)C2(C)OC1=O)C1=C(C)CC(O)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O7/c1-4-5-6-7-8-9-19(29)24-25-18-14-33-21(23-15(2)10-17(28)13-20(23)30)11-16(18)12-22(31)27(25,3)34-26(24)32/h11-12,14,17,28H,4-10,13H2,1-3H3

> <INCHI_KEY>
QMIVTDDJTVQZLY-UHFFFAOYSA-N

> <FORMULA>
C27H30O7

> <MOLECULAR_WEIGHT>
466.53

> <EXACT_MASS>
466.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.82044182255456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_LOGP>
3.398240501666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.585735606863704

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.994138577506433

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7963155586551736

> <JCHEM_POLAR_SURFACE_AREA>
106.97

> <JCHEM_REFRACTIVITY>
128.57669999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.261  -6.263   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.928  -5.493   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.594  -6.263   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.260  -5.493   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.926  -6.263   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.593  -5.493   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.259  -6.263   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.925  -5.493   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.925  -3.953   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.408  -6.263   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.815  -5.637   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.291  -4.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.261  -3.028   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.736  -1.563   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.243  -1.243   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.719   0.222   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.688   1.366   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.182   1.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.164   2.831   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.670   3.151   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.146   4.616   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.701   2.007   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.225   0.542   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.255  -0.602   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.273  -2.387   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.797  -3.852   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.828  -4.996   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.352  -6.461   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.382  -7.605   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.846  -6.781   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.751  -8.027   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.076  -8.115   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.569  -7.795   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.575  -8.825   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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12   30                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23                                                            
CONECT   25   15   26                                                       
CONECT   26   25   12   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   11   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   10   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₇

Average Mass

466.5300 Da

Monoisotopic Mass

466.19915 Da

IUPAC Name

3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

Traditional Name

3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)C1=C2C3=COC(=CC3=CC(=O)C2(C)OC1=O)C1=C(C)CC(O)CC1=O

InChI Identifier

InChI=1S/C27H30O7/c1-4-5-6-7-8-9-19(29)24-25-18-14-33-21(23-15(2)10-17(28)13-20(23)30)11-16(18)12-22(31)27(25,3)34-26(24)32/h11-12,14,17,28H,4-10,13H2,1-3H3

InChI Key

QMIVTDDJTVQZLY-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
Jackrogersella minutella	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Cyclohexenone
Alpha-acyloxy ketone
Pyran
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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
logP	3.4	ChemAxon
pKa (Strongest Acidic)	14.99	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	128.58 m³·mol⁻¹	ChemAxon
Polarizability	50.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162815186

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione (NP0224195)

MOL for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

3D MOL for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

3D SDF for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

3D-SDF for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

PDB for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

3D PDB for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

SMILES for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

INCHI for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

Structure for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)

3D Structure for NP0224195 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione)