NP-MRD: Showing NP-Card for cohaerin E (NP0029656)

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Record Information

Version

2.0

Created at

2021-06-19 21:13:41 UTC

Updated at

2021-06-29 23:57:10 UTC

NP-MRD ID

NP0029656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cohaerin E

Provided By

JEOL Database JEOL Logo

Description

cohaerin E is found in Annulohypoxylon cohaerens. cohaerin E was first documented in 2006 (Quang, D. N., et al.). Based on a literature review very few articles have been published on (6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-[(2S)-2-methyloctanoyl]-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123133D          

 64 67  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192123133D          

 64 67  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0029656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C(=C1C1=C([H])C2=C([H])C(=O)[C@@]3(OC(=O)C(C(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=C3C2=C([H])O1)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O6/c1-5-6-7-8-10-17(3)26(31)24-25-19-15-33-21(23-16(2)11-9-12-20(23)29)13-18(19)14-22(30)28(25,4)34-27(24)32/h9,11-15,17,29H,5-8,10H2,1-4H3/t17-,28-/m0/s1

> <INCHI_KEY>
BNPNEDGQFYVZTE-HPGBDJQBSA-N

> <FORMULA>
C28H30O6

> <MOLECULAR_WEIGHT>
462.542

> <EXACT_MASS>
462.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.80325685943874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-[(2S)-2-methyloctanoyl]-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

> <ALOGPS_LOGP>
5.59

> <JCHEM_LOGP>
5.743631604666667

> <ALOGPS_LOGS>
-5.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.842489827402876

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.064182062901105

> <JCHEM_PKA_STRONGEST_BASIC>
-5.242189633431766

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
131.7772

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-[(2S)-2-methyloctanoyl]furo[2,3-h]isochromene-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       2.991  -2.671  -3.162  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.221  -3.405  -2.075  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.735  -3.049  -2.111  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.109  -3.812  -1.085  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.286  -3.500   0.359  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.714  -4.084   1.364  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.248  -3.909   2.819  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.200  -4.611   3.785  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.169  -2.428   3.183  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.172  -1.717   3.242  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.165  -1.842   3.416  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.731  -0.774   2.847  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.290   0.111   1.786  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.056   0.642   1.708  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.375   1.491   0.701  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.499   1.781  -0.342  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.047   2.677  -1.374  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.292   2.228  -2.692  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.077   0.795  -3.100  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.749   3.142  -3.658  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.981   4.477  -3.329  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.768   4.917  -2.027  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.315   4.023  -1.060  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.146   4.539   0.199  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.772   1.347  -0.365  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.243   0.527   0.739  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.529   0.136   0.797  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.027  -0.652   1.964  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.111  -1.224   1.869  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.163  -0.664   3.245  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.470   0.576   4.087  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.384  -1.807   4.061  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.212  -2.478   4.219  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.063  -3.467   4.912  0.00  0.00           O+0
HETATM   35  H   UNK     0       2.907  -1.586  -3.036  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.052  -2.937  -3.120  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.614  -2.932  -4.156  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.654  -3.141  -1.104  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.348  -4.486  -2.208  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.336  -3.261  -3.111  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.615  -1.972  -1.946  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.027  -4.891  -1.266  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.161  -3.543  -1.240  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.283  -3.904   0.567  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.338  -2.414   0.483  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.847  -5.153   1.156  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.692  -3.606   1.219  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.740  -4.373   2.921  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.879  -4.465   4.822  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.220  -4.221   3.697  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.231  -5.687   3.587  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.751   0.481   2.411  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.507   0.592  -4.088  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.992   0.567  -3.148  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.570   0.118  -2.395  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.934   2.815  -4.680  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.337   5.172  -4.085  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.958   5.954  -1.761  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.081   3.795   0.822  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.449   1.620  -1.170  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.264   0.369   0.036  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.516   0.564   4.415  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.306   1.509   3.537  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.858   0.600   4.997  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    3    1   38   39                                             
CONECT    3    4    2   40   41                                             
CONECT    4    5    3   42   43                                             
CONECT    5    4    6   44   45                                             
CONECT    6    7    5   46   47                                             
CONECT    7    6    9    8   48                                             
CONECT    8    7   49   50   51                                             
CONECT    9    7   11   10                                                  
CONECT   10    9                                                            
CONECT   11   33   12    9                                                  
CONECT   12   13   30   11                                                  
CONECT   13   12   26   14                                                  
CONECT   14   13   15   52                                                  
CONECT   15   14   16                                                       
CONECT   16   17   15   25                                                  
CONECT   17   23   18   16                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   53   54   55                                             
CONECT   20   21   18   56                                                  
CONECT   21   22   20   57                                                  
CONECT   22   23   21   58                                                  
CONECT   23   17   22   24                                                  
CONECT   24   23   59                                                       
CONECT   25   26   16   60                                                  
CONECT   26   27   13   25                                                  
CONECT   27   28   26   61                                                  
CONECT   28   30   27   29                                                  
CONECT   29   28                                                            
CONECT   30   28   12   32   31                                             
CONECT   31   30   62   63   64                                             
CONECT   32   30   33                                                       
CONECT   33   32   11   34                                                  
CONECT   34   33                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    2                                                            
CONECT   39    2                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    5                                                            
CONECT   46    6                                                            
CONECT   47    6                                                            
CONECT   48    7                                                            
CONECT   49    8                                                            
CONECT   50    8                                                            
CONECT   51    8                                                            
CONECT   52   14                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   27                                                            
CONECT   62   31                                                            
CONECT   63   31                                                            
CONECT   64   31                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  134    0
END

RDKit          3D

64 67  0  0  0  0  0  0  0  0999 V2000
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    3.1633   -0.6635    3.2455 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4703    0.5764    4.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837   -1.8074    4.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2121   -2.4775    4.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -3.4672    4.9120 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0516   -2.9367   -3.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6137   -2.9320   -4.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6538   -3.1411   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8790   -4.4651    4.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5165    0.5638    4.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3063    1.5089    3.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    0.6002    4.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 23  1  0
 28 30  1  0
  5  4  1  0
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 19 55  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₆

Average Mass

462.5420 Da

Monoisotopic Mass

462.20424 Da

IUPAC Name

(6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-[(2S)-2-methyloctanoyl]-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

Traditional Name

(6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-[(2S)-2-methyloctanoyl]furo[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C([H])C(=C1C1=C([H])C2=C([H])C(=O)[C@@]3(OC(=O)C(C(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=C3C2=C([H])O1)C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C28H30O6/c1-5-6-7-8-10-17(3)26(31)24-25-19-15-33-21(23-16(2)11-9-12-20(23)29)13-18(19)14-22(30)28(25,4)34-27(24)32/h9,11-15,17,29H,5-8,10H2,1-4H3/t17-,28-/m0/s1

InChI Key

BNPNEDGQFYVZTE-HPGBDJQBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annulohypoxylon cohaerens	JEOL database	Quang, D. N., et al, Tetrahedron 62, 6349 (2006)

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
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Phenol
Alpha-acyloxy ketone
Toluene
Monocyclic benzene moiety
2-furanone
Benzenoid
Pyran
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	5.59	ALOGPS
logP	5.74	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	131.78 m³·mol⁻¹	ChemAxon
Polarizability	49.8 Å³	ChemAxon
Number of Rings	4	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

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

73212562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Quang, D. N., et al. (2006). Quang, D. N., et al, Tetrahedron 62, 6349 (2006). Tetrahedron.

Showing NP-Card for cohaerin E (NP0029656)

MOL for NP0029656 (cohaerin E)

3D MOL for NP0029656 (cohaerin E)

3D SDF for NP0029656 (cohaerin E)

3D-SDF for NP0029656 (cohaerin E)

PDB for NP0029656 (cohaerin E)

3D PDB for NP0029656 (cohaerin E)

SMILES for NP0029656 (cohaerin E)

INCHI for NP0029656 (cohaerin E)

Structure for NP0029656 (cohaerin E)

3D Structure for NP0029656 (cohaerin E)