NP-MRD: Showing NP-Card for 3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione (NP0301602)

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Record Information

Version

2.0

Created at

2022-09-10 14:40:34 UTC

Updated at

2022-09-10 14:40:35 UTC

NP-MRD ID

NP0301602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

3-(4-Hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione is found in Annulohypoxylon cohaerens. 3-(4-Hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251511112D          

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M  END

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M  END


  Mrv1533004251511112D          

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 25 26  2  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0301602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(C)C(=O)C1C2C3=COC(=CC3=CC(=O)C2(C)OC1=O)C1=C(C)CC(O)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O7/c1-5-6-7-8-9-15(2)26(32)24-25-19-14-34-21(23-16(3)10-18(29)13-20(23)30)11-17(19)12-22(31)28(25,4)35-27(24)33/h11-12,14-15,18,24-25,29H,5-10,13H2,1-4H3

> <INCHI_KEY>
GKKNMNFXYPXAOJ-UHFFFAOYSA-N

> <FORMULA>
C28H34O7

> <MOLECULAR_WEIGHT>
482.573

> <EXACT_MASS>
482.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.72269546296856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
3.8232098406666664

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.994302745998148

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.465205319034991

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7963155586442623

> <JCHEM_POLAR_SURFACE_AREA>
106.97000000000003

> <JCHEM_REFRACTIVITY>
132.61889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.93e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         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      -2.259  -7.803   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.925  -5.493   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.925  -3.953   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.408  -6.263   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.815  -5.637   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.291  -4.172   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.261  -3.028   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.736  -1.563   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.243  -1.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.273  -2.387   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.797  -3.852   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.828  -4.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.352  -6.461   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.382  -7.605   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.846  -6.781   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.751  -8.027   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.076  -8.115   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.569  -7.795   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.575  -8.825   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.719   0.222   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.688   1.366   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.182   1.046   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.164   2.831   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.670   3.151   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.146   4.616   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.701   2.007   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.225   0.542   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.255  -0.602   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    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   25                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   12   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   11   26                                                  
CONECT   26   25                                                            
CONECT   27   16   28   34                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   27   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₇

Average Mass

482.5730 Da

Monoisotopic Mass

482.23045 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCCCC(C)C(=O)C1C2C3=COC(=CC3=CC(=O)C2(C)OC1=O)C1=C(C)CC(O)CC1=O

InChI Identifier

InChI=1S/C28H34O7/c1-5-6-7-8-9-15(2)26(32)24-25-19-14-34-21(23-16(3)10-18(29)13-20(23)30)11-17(19)12-22(31)28(25,4)35-27(24)33/h11-12,14-15,18,24-25,29H,5-10,13H2,1-4H3

InChI Key

GKKNMNFXYPXAOJ-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
Annulohypoxylon cohaerens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-acyloxy ketone
Gamma butyrolactone
Pyran
1,3-dicarbonyl compound
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
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	3.69	ALOGPS
logP	3.82	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	11.47	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	132.62 m³·mol⁻¹	ChemAxon
Polarizability	52.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

73068007

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-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione (NP0301602)

MOL for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D MOL for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D SDF for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D-SDF for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

PDB for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D PDB for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

SMILES for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

INCHI for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

Structure for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D Structure for NP0301602 (3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)