NP-MRD: Showing NP-Card for (2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid (NP0181314)

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Record Information

Version

2.0

Created at

2022-09-03 19:48:49 UTC

Updated at

2022-09-03 19:48:49 UTC

NP-MRD ID

NP0181314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid

Description

ACT-Toxin II belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. (2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid is found in Alternaria alternata. Based on a literature review very few articles have been published on ACT-Toxin II.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032221482D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032221482D          

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  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 30 20  1  6  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 30 33  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)CC(C)(O)C(O)C(O)C(O)=NC(C(C)C)C(=O)O[C@H](\C=C\C=C/C=C/C(O)=O)[C@]1(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C26H39NO9/c1-7-17(4)14-25(5,34)22(31)21(30)23(32)27-20(16(2)3)24(33)36-18(26(6)15-35-26)12-10-8-9-11-13-19(28)29/h7-13,16,18,20-22,30-31,34H,14-15H2,1-6H3,(H,27,32)(H,28,29)/b9-8-,12-10+,13-11+,17-7+/t18-,20?,21?,22?,25?,26+/m1/s1

> <INCHI_KEY>
JFCZKYSQJFCXMV-PUEBJXPXSA-N

> <FORMULA>
C26H39NO9

> <MOLECULAR_WEIGHT>
509.596

> <EXACT_MASS>
509.26248184

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.7696668084804

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4Z,6E,8R)-8-[(3-methyl-2-{[(6E)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2S)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid

> <JCHEM_LOGP>
2.551080916

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.243119514897309

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.433858157519009

> <JCHEM_PKA_STRONGEST_BASIC>
0.5749090733566945

> <JCHEM_POLAR_SURFACE_AREA>
169.41

> <JCHEM_REFRACTIVITY>
136.28000000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z,6E,8R)-8-[(3-methyl-2-{[(6E)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2S)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.634 -12.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.404 -11.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.944 -11.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.714 -12.413   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.714  -9.745   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.944  -8.412   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.277  -7.642   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.610  -9.182   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.174  -7.078   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.634  -7.078   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.944  -5.744   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.484  -5.744   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.174  -4.411   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.634  -4.411   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       6.944  -3.077   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.174  -1.743   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.634  -1.743   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.864  -3.077   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.864  -0.410   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.324  -0.410   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.554   0.924   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.014   0.924   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.756   2.258   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.296   2.258   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.066   0.924   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.606   0.924   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.376  -0.410   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.916  -0.410   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.606  -1.743   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.554  -1.743   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.106  -1.217   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.733  -2.733   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.286  -3.260   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.944  -0.410   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.174   0.924   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.484  -0.410   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   20   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   30                                                       
CONECT   34   16   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₉NO₉

Average Mass

509.5960 Da

Monoisotopic Mass

509.26248 Da

IUPAC Name

(2E,4Z,6E,8R)-8-[(3-methyl-2-{[(6E)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2S)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid

Traditional Name

(2E,4Z,6E,8R)-8-[(3-methyl-2-{[(6E)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2S)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid

CAS Registry Number

Not Available

SMILES

C\C=C(/C)CC(C)(O)C(O)C(O)C(O)=NC(C(C)C)C(=O)O[C@H](\C=C\C=C/C=C/C(O)=O)[C@]1(C)CO1

InChI Identifier

InChI=1S/C26H39NO9/c1-7-17(4)14-25(5,34)22(31)21(30)23(32)27-20(16(2)3)24(33)36-18(26(6)15-35-26)12-10-8-9-11-13-19(28)29/h7-13,16,18,20-22,30-31,34H,14-15H2,1-6H3,(H,27,32)(H,28,29)/b9-8-,12-10+,13-11+,17-7+/t18-,20?,21?,22?,25?,26+/m1/s1

InChI Key

JFCZKYSQJFCXMV-PUEBJXPXSA-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
Alternaria alternata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
Valine or derivatives
N-acyl-alpha amino acid or derivatives
Medium-chain fatty acid
Amino fatty acid
Branched fatty acid
Fatty acid ester
Heterocyclic fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Monosaccharide
N-acyl-amine
Unsaturated fatty acid
Tertiary alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid ester
Organoheterocyclic compound
Polyol
Oxacycle
Ether
Oxirane
Carboxylic acid
Dialkyl ether
Carbonyl group
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Organonitrogen compound
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	2.55	ChemAxon
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	0.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	169.41 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	136.28 m³·mol⁻¹	ChemAxon
Polarizability	53.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

101065734

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid (NP0181314)

MOL for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

3D MOL for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

3D SDF for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

3D-SDF for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

PDB for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

3D PDB for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

SMILES for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

INCHI for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

Structure for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)

3D Structure for NP0181314 ((2e,4z,6e,8r)-8-[(3-methyl-2-{[(6e)-1,2,3,4-tetrahydroxy-4,6-dimethyloct-6-en-1-ylidene]amino}butanoyl)oxy]-8-[(2s)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid)