NP-MRD: Showing NP-Card for Eremoxylarin E (NP0341944)

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Record Information

Version

2.0

Created at

2024-11-07 15:48:17 UTC

Updated at

2024-11-09 00:02:48 UTC

NP-MRD ID

NP0341944

Natural Product DOI

https://doi.org/10.57994/3434

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eremoxylarin E

Description

Eremoxylarin E was first documented in 2023 (PMID: 36892834).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02042315592D          

 31 32  0  0  1  0            999 V2000
   -8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0026   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.7171   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  2  0  0  0  0
 20 27  2  0  0  0  0
 17 28  1  6  0  0  0
 16 29  1  1  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END


  Mrv2104 02042315592D          

 31 32  0  0  1  0            999 V2000
   -8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0026   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.7171   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  2  0  0  0  0
 20 27  2  0  0  0  0
 17 28  1  6  0  0  0
 16 29  1  1  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0341944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C\C=C\C(=O)O[C@H]1CC[C@H](C(O)=O)[C@]2(C)C[C@H](C(=C)C=O)C(=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O6/c1-4-5-6-7-8-9-10-11-23(28)31-22-13-12-19(24(29)30)25(3)15-18(17(2)16-26)21(27)14-20(22)25/h8-11,14,16,18-19,22H,2,4-7,12-13,15H2,1,3H3,(H,29,30)/b9-8+,11-10+/t18-,19-,22+,25+/m1/s1

> <INCHI_KEY>
QKVBUVBTWKKCBC-RNAXTMPPSA-N

> <FORMULA>
C25H32O6

> <MOLECULAR_WEIGHT>
428.525

> <EXACT_MASS>
428.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.41636076957681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,7R,8aS)-4-[(2E,4E)-deca-2,4-dienoyloxy]-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <JCHEM_LOGP>
4.816671770000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.382295681444385

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.145206464774757

> <JCHEM_PKA_STRONGEST_BASIC>
-5.013896415809142

> <JCHEM_POLAR_SURFACE_AREA>
97.74000000000001

> <JCHEM_REFRACTIVITY>
120.29029999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,7R,8aS)-4-[(2E,4E)-deca-2,4-dienoyloxy]-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-FEB-23         0                                  
HETATM    1  O   UNK     0     -16.004  -9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0     -16.004  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.670  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -21.339  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -20.005  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -22.673  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -24.006  -0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -22.673  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -18.672  -1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -18.672  -0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -16.004  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18   22   28                                             
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   20                                                            
CONECT   28   17                                                            
CONECT   29   16   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₆

Average Mass

428.5250 Da

Monoisotopic Mass

428.21989 Da

IUPAC Name

(1S,4S,7R,8aS)-4-[(2E,4E)-deca-2,4-dienoyloxy]-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

(1S,4S,7R,8aS)-4-[(2E,4E)-deca-2,4-dienoyloxy]-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C\C=C\C(=O)O[C@H]1CC[C@H](C(O)=O)[C@]2(C)C[C@H](C(=C)C=O)C(=O)C=C12

InChI Identifier

InChI=1S/C25H32O6/c1-4-5-6-7-8-9-10-11-23(28)31-22-13-12-19(24(29)30)25(3)15-18(17(2)16-26)21(27)14-20(22)25/h8-11,14,16,18-19,22H,2,4-7,12-13,15H2,1,3H3,(H,29,30)/b9-8+,11-10+/t18-,19-,22+,25+/m1/s1

InChI Key

QKVBUVBTWKKCBC-RNAXTMPPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C6D6, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C6D6, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C6D6, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C3D6O, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	solenn.ferron@univ-rennes.fr	Université de Rennes	Alice Miral	2024-11-07	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500, C3D6O, simulated)	solenn.ferron@univ-rennes.fr	Université de Rennes	Solenn	2024-11-07	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Hypoxylon		Not Available

Chemical Taxonomy

Classification

Not classified

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	4.82	ChemAxon
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.74 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	120.29 m³·mol⁻¹	ChemAxon
Polarizability	47.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miral A, Ferron S, Rouaud I, Slyambayev D, Bousarghin L, Camuzet C, Belouzard S, Seron K, Le Pogam P, Tranchimand S, Tomasi S: Eremoxylarins D-J, Antibacterial Eremophilane Sesquiterpenes Discovered from an Endolichenic Strain of Xylaria hypoxylon. J Nat Prod. 2023 Apr 28;86(4):730-738. doi: 10.1021/acs.jnatprod.2c00881. Epub 2023 Mar 9. [PubMed:36892834 ]

Showing NP-Card for Eremoxylarin E (NP0341944)

MOL for NP0341944 (Eremoxylarin E)

3D MOL for NP0341944 (Eremoxylarin E)

3D SDF for NP0341944 (Eremoxylarin E)

3D-SDF for NP0341944 (Eremoxylarin E)

PDB for NP0341944 (Eremoxylarin E)

3D PDB for NP0341944 (Eremoxylarin E)

SMILES for NP0341944 (Eremoxylarin E)

INCHI for NP0341944 (Eremoxylarin E)

Structure for NP0341944 (Eremoxylarin E)

3D Structure for NP0341944 (Eremoxylarin E)