NP-MRD: Showing NP-Card for Eutypellin A (NP0008718)

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Record Information

Version

2.0

Created at

2020-12-09 06:14:36 UTC

Updated at

2021-07-15 17:01:13 UTC

NP-MRD ID

NP0008718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eutypellin A

Provided By

NPAtlas

Description

Eutypellin A belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Eutypellin A is found in Eutypella. Eutypellin A was first documented in 2009 (PMID: 19739600). Based on a literature review very few articles have been published on Eutypellin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106123D          

 28 28  0  0  0  0            999 V2000
   -5.7752   -0.0687   -2.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5627   -0.0132   -2.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1486   -0.2417   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813   -0.1954   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019   -0.4301    0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254   -0.3719    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6281   -0.5707    2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2537   -1.0399    3.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.1654    2.4201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.4077    1.0707 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2546    0.4625    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1923    0.0240   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3759    0.8532   -0.4922 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2514    2.0713    0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1145   -0.0856    0.2260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0726   -0.9815   -0.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    0.2063   -3.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8658   -0.4632   -0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1333    0.0216   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522   -0.6515    1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3665   -1.4855    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3689    1.4623    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1423   -0.9663   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4509    0.9621   -1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3024    0.3399   -0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706    2.7185   -0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    0.9368   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403   -1.9201   -0.5291 H   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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15  6  1  0  0  0  0
  2 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4 19  1  0  0  0  0
  5 20  1  0  0  0  0
 10 21  1  1  0  0  0
 11 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 13 25  1  0  0  0  0
 14 26  1  0  0  0  0
 15 27  1  6  0  0  0
 16 28  1  0  0  0  0
M  END


  Mrv1652306242106123D          

 28 28  0  0  0  0            999 V2000
   -5.7752   -0.0687   -2.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5627   -0.0132   -2.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1486   -0.2417   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813   -0.1954   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019   -0.4301    0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254   -0.3719    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6281   -0.5707    2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2537   -1.0399    3.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.1654    2.4201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.4077    1.0707 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2546    0.4625    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1923    0.0240   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3759    0.8532   -0.4922 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2514    2.0713    0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1145   -0.0856    0.2260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0726   -0.9815   -0.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    0.2063   -3.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8658   -0.4632   -0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1333    0.0216   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522   -0.6515    1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3665   -1.4855    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3689    1.4623    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1423   -0.9663   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4509    0.9621   -1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3024    0.3399   -0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706    2.7185   -0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    0.9368   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403   -1.9201   -0.5291 H   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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15  6  1  0  0  0  0
  2 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4 19  1  0  0  0  0
  5 20  1  0  0  0  0
 10 21  1  1  0  0  0
 11 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 13 25  1  0  0  0  0
 14 26  1  0  0  0  0
 15 27  1  6  0  0  0
 16 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(\[H])=C(/[H])[C@@]1([H])OC(=O)\C(=C(/[H])\C(\[H])=C(/[H])C([H])=O)[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O5/c12-6-2-1-4-8-10(14)9(5-3-7-13)16-11(8)15/h1-6,9-10,13-14H,7H2/b2-1+,5-3+,8-4+/t9-,10+/m1/s1

> <INCHI_KEY>
CBOVMILAWSSPKZ-ISKCKYDESA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.212

> <EXACT_MASS>
224.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.48224982490772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-4-[(3E,4S,5R)-4-hydroxy-5-[(1E)-3-hydroxyprop-1-en-1-yl]-2-oxooxolan-3-ylidene]but-2-enal

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
-0.39318533033333314

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.633261771415441

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.223020356566547

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5231455276136776

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
58.88340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eutypellin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -5.775  -0.069  -2.645  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.563  -0.013  -2.334  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.149  -0.242  -0.957  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.881  -0.195  -0.572  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.502  -0.430   0.819  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.225  -0.372   1.148  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.628  -0.571   2.462  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.254  -1.040   3.466  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.714  -0.165   2.420  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.116  -0.408   1.071  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.255   0.463   0.729  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.192   0.024  -0.102  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.376   0.853  -0.492  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.251   2.071   0.170  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.115  -0.086   0.226  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.073  -0.982  -0.858  0.00  0.00           O+0
HETATM   17  H   UNK     0      -3.851   0.206  -3.110  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.866  -0.463  -0.174  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.133   0.022  -1.317  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.252  -0.652   1.586  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.367  -1.486   1.022  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.369   1.462   1.129  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.142  -0.966  -0.540  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.451   0.962  -1.587  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.302   0.340  -0.145  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.871   2.719  -0.251  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.100   0.937  -0.154  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.040  -1.920  -0.529  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   15   21                                             
CONECT   11   10   12   22                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14   24   25                                             
CONECT   14   13   26                                                       
CONECT   15   10   16    6   27                                             
CONECT   16   15   28                                                       
CONECT   17    2                                                            
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    5                                                            
CONECT   21   10                                                            
CONECT   22   11                                                            
CONECT   23   12                                                            
CONECT   24   13                                                            
CONECT   25   13                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
CONECT   28   16                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂O₅

Average Mass

224.2120 Da

Monoisotopic Mass

224.06847 Da

IUPAC Name

(2E)-4-[(3E,4S,5R)-4-hydroxy-5-[(1E)-3-hydroxyprop-1-en-1-yl]-2-oxooxolan-3-ylidene]but-2-enal

Traditional Name

eutypellin A

CAS Registry Number

Not Available

SMILES

OC\C=C\[C@H]1OC(=O)\C(=C\C=C\C=O)[C@@H]1O

InChI Identifier

InChI=1S/C11H12O5/c12-6-2-1-4-8-10(14)9(5-3-7-13)16-11(8)15/h1-6,9-10,13-14H,7H2/b2-1+,5-3+,8-4+/t9-,10+/m1/s1

InChI Key

CBOVMILAWSSPKZ-ISKCKYDESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Eutypella	NPAtlas	19739600

Species Where Detected

Species Name	Source	Reference
Eutypella sp. BCC13199	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Alpha,beta-unsaturated aldehyde
Enal
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Aldehyde
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.71	ALOGPS
logP	-0.39	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.88 m³·mol⁻¹	ChemAxon
Polarizability	22.48 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA016871

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047870

Chemspider ID

24531944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44479732

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Isaka M, Palasarn S, Lapanun S, Chanthaket R, Boonyuen N, Lumyong S: Gamma-lactones and ent-eudesmane sesquiterpenes from the endophytic fungus Eutypella sp. BCC 13199. J Nat Prod. 2009 Sep;72(9):1720-2. doi: 10.1021/np900316x. [PubMed:19739600 ]

Showing NP-Card for Eutypellin A (NP0008718)

MOL for NP0008718 (Eutypellin A)

3D MOL for NP0008718 (Eutypellin A)

3D SDF for NP0008718 (Eutypellin A)

3D-SDF for NP0008718 (Eutypellin A)

PDB for NP0008718 (Eutypellin A)

3D PDB for NP0008718 (Eutypellin A)

SMILES for NP0008718 (Eutypellin A)

INCHI for NP0008718 (Eutypellin A)

Structure for NP0008718 (Eutypellin A)

3D Structure for NP0008718 (Eutypellin A)