NP-MRD: Showing NP-Card for (2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid (NP0315741)

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Record Information

Version

2.0

Created at

2022-09-11 14:31:30 UTC

Updated at

2022-09-11 14:31:30 UTC

NP-MRD ID

NP0315741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

Description

AK toxin I, also known as ak-toxin I, 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)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid is found in Alternaria alternata and Alternaria kikuchiana. AK toxin I is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218072D          

 30 31  0  0  0  0            999 V2000
    0.6488   -2.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -3.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -3.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619   -1.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -2.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -0.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -0.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5673    0.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619    0.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804    1.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804    3.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412    3.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2712    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519    2.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1351   -0.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7035    0.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    0.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2974    1.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281   -0.4050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089    0.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6220    0.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281   -2.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9205    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -0.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9205    3.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  7 27  1  0  0  0  0
  8  9  1  0  0  0  0
  8 24  1  0  0  0  0
  9 10  1  0  0  0  0
  9 29  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 30  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 28  1  0  0  0  0
M  END


  Mrv0541 02241218072D          

 30 31  0  0  0  0            999 V2000
    0.6488   -2.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -3.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -3.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619   -1.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -2.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -0.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488   -0.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5673    0.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619    0.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804    1.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804    3.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412    3.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2712    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519    2.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1351   -0.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7035    0.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    0.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2974    1.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281   -0.4050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089    0.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6220    0.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281   -2.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9205    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -0.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9205    3.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  7 27  1  0  0  0  0
  8  9  1  0  0  0  0
  8 24  1  0  0  0  0
  9 10  1  0  0  0  0
  9 29  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 30  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(NC(C)=O)C(=O)OC(\C=C\C=C/C=C/C(O)=O)C1(C)CO1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H27NO6/c1-16(18-11-7-6-8-12-18)21(24-17(2)25)22(28)30-19(23(3)15-29-23)13-9-4-5-10-14-20(26)27/h4-14,16,19,21H,15H2,1-3H3,(H,24,25)(H,26,27)/b5-4-,13-9+,14-10+

> <INCHI_KEY>
HGSOUJPIFSDBKJ-OUYMFVGOSA-N

> <FORMULA>
C23H27NO6

> <MOLECULAR_WEIGHT>
413.4636

> <EXACT_MASS>
413.183837601

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
44.08390870570392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z,6E)-8-[(2-acetamido-3-phenylbutanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
2.800758441

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.543434523109024

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.150560712812296

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1869247625578923

> <JCHEM_POLAR_SURFACE_AREA>
105.23

> <JCHEM_REFRACTIVITY>
113.96939999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z,6E)-8-[(2-acetamido-3-phenylbutanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.211  -5.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.150  -6.208   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.514  -5.602   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.514  -4.087   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.302  -3.331   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.211  -3.937   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.423  -3.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.423  -1.513   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.211  -0.756   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.059   0.757   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.302   1.514   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.150   3.029   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.211   3.786   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.211   5.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.150   6.058   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.514   5.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.877   6.058   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.240   5.301   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.390   3.786   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.119  -0.605   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.180   0.456   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.665   0.908   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.422   2.271   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       3.786  -0.756   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.937   0.757   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.028   1.817   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.786  -3.784   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.452   1.211   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.150  -1.362   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.452   6.208   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18                                                            
CONECT   20   21   22                                                       
CONECT   21   20   22                                                       
CONECT   22   11   20   21   23                                             
CONECT   23   22                                                            
CONECT   24    8   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25                                                            
CONECT   27    7                                                            
CONECT   28   25                                                            
CONECT   29    9                                                            
CONECT   30   18                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
AK-toxin I	HMDB
N-Acetyl-b-methyl-L-phenylalanine 7-carboxy-1-(2-methyloxiranyl)-2,4,6-heptatrienyl ester, 9ci	HMDB

Chemical Formula

C₂₃H₂₇NO₆

Average Mass

413.4636 Da

Monoisotopic Mass

413.18384 Da

IUPAC Name

(2E,4Z,6E)-8-[(2-acetamido-3-phenylbutanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

Traditional Name

(2E,4Z,6E)-8-[(2-acetamido-3-phenylbutanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

CAS Registry Number

Not Available

SMILES

CC(C(NC(C)=O)C(=O)OC(\C=C\C=C/C=C/C(O)=O)C1(C)CO1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C23H27NO6/c1-16(18-11-7-6-8-12-18)21(24-17(2)25)22(28)30-19(23(3)15-29-23)13-9-4-5-10-14-20(26)27/h4-14,16,19,21H,15H2,1-3H3,(H,24,25)(H,26,27)/b5-4-,13-9+,14-10+

InChI Key

HGSOUJPIFSDBKJ-OUYMFVGOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alternaria alternata	LOTUS Database	35616633
Alternaria kikuchiana	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
N-acyl-alpha amino acid or derivatives
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Acetamide
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic molecular entity (CHEBI:80727 )

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	3.49	ALOGPS
logP	2.8	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.23 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	113.97 m³·mol⁻¹	ChemAxon
Polarizability	44.08 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

HMDB0030401

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173828

PDB ID

Not Available

ChEBI ID

80727

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid (NP0315741)

MOL for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

3D MOL for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

3D SDF for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

3D-SDF for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

PDB for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

3D PDB for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

SMILES for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

INCHI for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

Structure for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)

3D Structure for NP0315741 ((2e,4z,6e)-8-({2-[(1-hydroxyethylidene)amino]-3-phenylbutanoyl}oxy)-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid)