NP-MRD: Showing NP-Card for n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid (NP0298356)

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Record Information

Version

2.0

Created at

2022-09-10 09:33:16 UTC

Updated at

2022-09-10 09:33:16 UTC

NP-MRD ID

NP0298356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid

Description

NSC226667 belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review very few articles have been published on NSC226667.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102211332D          

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M  END

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  Mrv1652309102211332D          

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    3.3725   -1.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3688   -0.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8347    0.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897    0.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377    1.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0976    2.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094    1.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6657    2.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    3.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2971    2.9523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9447    2.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6273    2.8374    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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  2  0  0  0  0
 39 38  1  4  0  0  0
 39 40  2  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1N=C(O)C(N=C(O)C(CC2=CC=CC=C2)NC)C(OC2=CC=C(C=C2)\C=C/N=C1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H38N4O4/c1-4-22(2)28-32(39)35-20-19-23-15-17-26(18-16-23)41-30(25-13-9-6-10-14-25)29(33(40)36-28)37-31(38)27(34-3)21-24-11-7-5-8-12-24/h5-20,22,27-30,34H,4,21H2,1-3H3,(H,35,39)(H,36,40)(H,37,38)/b20-19-

> <INCHI_KEY>
JDFUVCMEHULMNF-VXPUYCOJSA-N

> <FORMULA>
C33H38N4O4

> <MOLECULAR_WEIGHT>
554.691

> <EXACT_MASS>
554.28930572

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.33223330262143

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(10Z)-7-(butan-2-yl)-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid

> <JCHEM_LOGP>
-0.8999182739774458

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
-4.319157184857882

> <JCHEM_PKA_STRONGEST_ACIDIC>
-9.570366374888575

> <JCHEM_PKA_STRONGEST_BASIC>
14.974950651930499

> <JCHEM_POLAR_SURFACE_AREA>
119.03000000000002

> <JCHEM_REFRACTIVITY>
159.85540000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(10Z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      15.629   2.074   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.100   1.887   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.174   3.118   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.777   4.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.645   2.931   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      11.479   1.385   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      10.666   0.061   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.769  -1.014   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.361  -0.786   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.894  -2.231   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.412  -2.492   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.397  -1.308   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.945  -3.937   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.463  -4.197   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.448  -3.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.915  -1.568   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.899  -0.384   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.417  -0.645   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.950  -2.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.966  -3.274   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      10.961  -5.121   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      11.494  -6.565   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.805  -0.991   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.685  -2.527   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.955  -3.398   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.835  -4.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.445  -5.597   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.175  -4.726   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.295  -3.191   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.288  -0.544   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.291   0.733   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.088   1.752   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.364   3.274   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.782   3.941   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.924   2.914   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.701   1.394   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.843   5.163   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.303   5.825   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0       9.888   5.511   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0      11.097   4.432   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      12.371   5.296   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   40                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   13   22                                                       
CONECT   22   21                                                            
CONECT   23    9   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   23   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39    5   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₈N₄O₄

Average Mass

554.6910 Da

Monoisotopic Mass

554.28931 Da

IUPAC Name

N-[(10Z)-7-(butan-2-yl)-5,8-dihydroxy-3-phenyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid

Traditional Name

N-[(10Z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C1N=C(O)C(N=C(O)C(CC2=CC=CC=C2)NC)C(OC2=CC=C(C=C2)\C=C/N=C1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C33H38N4O4/c1-4-22(2)28-32(39)35-20-19-23-15-17-26(18-16-23)41-30(25-13-9-6-10-14-25)29(33(40)36-28)37-31(38)27(34-3)21-24-11-7-5-8-12-24/h5-20,22,27-30,34H,4,21H2,1-3H3,(H,35,39)(H,36,40)(H,37,38)/b20-19-

InChI Key

JDFUVCMEHULMNF-VXPUYCOJSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Phenylalanine or derivatives
Macrolactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Secondary carboxylic acid amide
Lactam
Amino acid or derivatives
Carboxamide group
Organoheterocyclic compound
Secondary amine
Ether
Secondary aliphatic amine
Azacycle
Oxacycle
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Organic oxide
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.9	ChemAxon
pKa (Strongest Acidic)	-9.6	ChemAxon
pKa (Strongest Basic)	14.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.03 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	159.86 m³·mol⁻¹	ChemAxon
Polarizability	59.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

20057243

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6299227

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid (NP0298356)

MOL for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

3D MOL for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

3D SDF for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

3D-SDF for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

PDB for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

3D PDB for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

SMILES for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

INCHI for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

Structure for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)

3D Structure for NP0298356 (n-[(10z)-5,8-dihydroxy-3-phenyl-7-(sec-butyl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-2-(methylamino)-3-phenylpropanimidic acid)