NP-MRD: Showing NP-Card for {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid (NP0172359)

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Record Information

Version

1.0

Created at

2022-09-03 09:15:03 UTC

Updated at

2022-09-03 09:15:03 UTC

NP-MRD ID

NP0172359

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid

Description

CHEMBL511439 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. {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid is found in Streptomyces hygroscopicus. Based on a literature review very few articles have been published on CHEMBL511439.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032211152D          

 37 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032211152D          

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    6.1475    1.3888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9699    1.3236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4377    2.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0830    2.7480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2601    1.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H](C)CC2=CC(NC(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(O)=N)\C(C)=C\[C@H](C)[C@H]1O)=CC=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40N2O7/c1-16-12-20-15-21(10-11-22(20)31)30-27(33)17(2)8-7-9-23(35-5)26(37-28(29)34)19(4)14-18(3)25(32)24(13-16)36-6/h7-11,14-16,18,23-26,31-32H,12-13H2,1-6H3,(H2,29,34)(H,30,33)/b9-7-,17-8+,19-14+/t16-,18+,23+,24+,25-,26+/m1/s1

> <INCHI_KEY>
FOTHSRVGKSQOSD-XJQIMXLASA-N

> <FORMULA>
C28H40N2O7

> <MOLECULAR_WEIGHT>
516.635

> <EXACT_MASS>
516.283551636

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.71803712179708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.0367701899778194

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.869805306858588

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.9178032882991642

> <JCHEM_PKA_STRONGEST_BASIC>
9.68626410378093

> <JCHEM_POLAR_SURFACE_AREA>
141.33

> <JCHEM_REFRACTIVITY>
156.6547

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic 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      12.799  -0.188   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.137   1.202   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.602   1.324   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.264  -0.066   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.391  -1.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.707  -1.275   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.485  -2.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.524  -3.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.216  -1.338   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.764  -1.851   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       6.654   0.138   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.997   1.690   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.462   1.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.800   3.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.673   4.470   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.011   5.861   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.208   4.349   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.870   2.958   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   5.617   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.419   7.008   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.884   7.129   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.292   8.276   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.827   8.154   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.700   9.423   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.038  10.813   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.489   6.764   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.616   5.495   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.024   6.642   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.898   7.910   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.686   5.252   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.813   3.983   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.278   4.105   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.475   2.593   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.011   2.471   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.884   3.739   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      13.222   5.130   0.000  0.00  0.00           N+0
HETATM   37  O   UNK     0      15.419   3.617   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17   12                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀N₂O₇

Average Mass

516.6350 Da

Monoisotopic Mass

516.28355 Da

IUPAC Name

{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid

Traditional Name

{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H](C)CC2=CC(NC(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(O)=N)\C(C)=C\[C@H](C)[C@H]1O)=CC=C2O

InChI Identifier

InChI=1S/C28H40N2O7/c1-16-12-20-15-21(10-11-22(20)31)30-27(33)17(2)8-7-9-23(35-5)26(37-28(29)34)19(4)14-18(3)25(32)24(13-16)36-6/h7-11,14-16,18,23-26,31-32H,12-13H2,1-6H3,(H2,29,34)(H,30,33)/b9-7-,17-8+,19-14+/t16-,18+,23+,24+,25-,26+/m1/s1

InChI Key

FOTHSRVGKSQOSD-XJQIMXLASA-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 hygroscopicus	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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Carbamic acid ester
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
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	3.29	ALOGPS
logP	2.04	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	-0.92	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	156.65 m³·mol⁻¹	ChemAxon
Polarizability	55.72 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

24714751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24992372

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid (NP0172359)

MOL for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D MOL for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D SDF for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D-SDF for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

PDB for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D PDB for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

SMILES for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

INCHI for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

Structure for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D Structure for NP0172359 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)