NP-MRD: Showing NP-Card for n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid (NP0322176)

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Record Information

Version

2.0

Created at

2022-09-12 00:48:12 UTC

Updated at

2022-09-12 00:48:12 UTC

NP-MRD ID

NP0322176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid

Description

N-[2,9-dihydroxy-7-methyl-5,6-dioxo-3-(propan-2-yl)-1,4,8-triazacyclotrideca-1,8-dien-10-yl]-6-methyloct-2-enimidic acid belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid is found in Streptomyces eurythermus. Based on a literature review very few articles have been published on N-[2,9-dihydroxy-7-methyl-5,6-dioxo-3-(propan-2-yl)-1,4,8-triazacyclotrideca-1,8-dien-10-yl]-6-methyloct-2-enimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202482D          

 32 32  0  0  0  0            999 V2000
   -3.1401    3.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256    2.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111    3.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111    4.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9967    2.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    3.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    2.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1467    3.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8612    2.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8612    2.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5757    3.3199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5757    4.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    3.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    4.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584    5.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755    6.0993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278    6.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2164    7.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0914    6.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800    7.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458    7.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323    7.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7436    6.7973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072    6.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1595    6.9901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    5.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3822    5.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9663    5.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    5.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776    4.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4253    3.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544    3.0249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
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  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  1  0  0  0  0
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 30 31  2  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 70 70  0  0  0  0  0  0  0  0999 V2000
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   -4.1267   -1.9484    0.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122202482D          

 32 32  0  0  0  0            999 V2000
   -3.1401    3.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256    2.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7584    5.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0322176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)CCC=CC(O)=NC1CCCN=C(O)C(NC(=O)C(=O)C(C)N=C1O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H38N4O5/c1-6-15(4)10-7-8-12-18(28)26-17-11-9-13-24-22(31)19(14(2)3)27-23(32)20(29)16(5)25-21(17)30/h8,12,14-17,19H,6-7,9-11,13H2,1-5H3,(H,24,31)(H,25,30)(H,26,28)(H,27,32)

> <INCHI_KEY>
AYUSCZXMHKYUPT-UHFFFAOYSA-N

> <FORMULA>
C23H38N4O5

> <MOLECULAR_WEIGHT>
450.58

> <EXACT_MASS>
450.28422034

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.573462897496526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2,9-dihydroxy-7-methyl-5,6-dioxo-3-(propan-2-yl)-1,4,8-triazacyclotrideca-1,8-dien-10-yl]-6-methyloct-2-enimidic acid

> <JCHEM_LOGP>
0.8285748335783678

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.154436730293691

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.945242148084545

> <JCHEM_PKA_STRONGEST_BASIC>
15.20495542281077

> <JCHEM_POLAR_SURFACE_AREA>
143.94

> <JCHEM_REFRACTIVITY>
123.22769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.862   6.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.528   5.427   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.194   6.197   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.194   7.737   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.860   5.427   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.527   6.197   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.807   5.427   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.141   6.197   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.474   5.427   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.474   3.887   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       4.808   6.197   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.808   7.737   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.359   7.217   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.416   8.434   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.282   9.707   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.128  11.385   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.345  12.328   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.137  13.854   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.771  11.745   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.563  13.271   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.752  14.581   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.780  14.214   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       6.988  12.688   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       8.413  12.105   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.631  13.048   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.621  10.579   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.047   9.996   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.404   9.636   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.978  10.219   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       7.612   8.110   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       6.394   7.168   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.635   5.647   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   12   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
N-[2,9-Dihydroxy-7-methyl-5,6-dioxo-3-(propan-2-yl)-1,4,8-triazacyclotrideca-1,8-dien-10-yl]-6-methyloct-2-enimidate	Generator

Chemical Formula

C₂₃H₃₈N₄O₅

Average Mass

450.5800 Da

Monoisotopic Mass

450.28422 Da

IUPAC Name

N-[2,9-dihydroxy-7-methyl-5,6-dioxo-3-(propan-2-yl)-1,4,8-triazacyclotrideca-1,8-dien-10-yl]-6-methyloct-2-enimidic acid

Traditional Name

N-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid

CAS Registry Number

Not Available

SMILES

CCC(C)CCC=CC(O)=NC1CCCN=C(O)C(NC(=O)C(=O)C(C)N=C1O)C(C)C

InChI Identifier

InChI=1S/C23H38N4O5/c1-6-15(4)10-7-8-12-18(28)26-17-11-9-13-24-22(31)19(14(2)3)27-23(32)20(29)16(5)25-21(17)30/h8,12,14-17,19H,6-7,9-11,13H2,1-5H3,(H,24,31)(H,25,30)(H,26,28)(H,27,32)

InChI Key

AYUSCZXMHKYUPT-UHFFFAOYSA-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
Streptomyces eurythermus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Cyclic carboximidic acid
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Cyclic ketone
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen 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	0.83	ChemAxon
pKa (Strongest Acidic)	-3.9	ChemAxon
pKa (Strongest Basic)	15.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	143.94 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	123.23 m³·mol⁻¹	ChemAxon
Polarizability	49.57 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

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

85116071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid (NP0322176)

MOL for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

3D MOL for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

3D SDF for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

3D-SDF for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

PDB for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

3D PDB for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

SMILES for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

INCHI for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

Structure for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)

3D Structure for NP0322176 (n-(2,9-dihydroxy-3-isopropyl-7-methyl-5,6-dioxo-1,4,8-triazacyclotrideca-1,8-dien-10-yl)-6-methyloct-2-enimidic acid)