NP-MRD: Showing NP-Card for {[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid (NP0185377)

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Record Information

Version

1.0

Created at

2022-09-04 00:45:46 UTC

Updated at

2022-09-04 00:45:47 UTC

NP-MRD ID

NP0185377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEMBL469932 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,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid is found in Streptomyces hygroscopicus. It was first documented in 2022 (PMID: 36057864). Based on a literature review a significant number of articles have been published on CHEMBL469932 (PMID: 36057863) (PMID: 36057862) (PMID: 36057861) (PMID: 36057860).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202452D          

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    9.3039    1.7600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0574    1.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1432    0.6035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7251    1.9086    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  4  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
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1CC\C=C(C)\C(O)=NC2=CC=CC(C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)\C=C(C)\[C@@H]1OC(O)=N)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H42N2O6/c1-17-13-21-10-8-11-22(16-21)30-27(32)18(2)9-7-12-23(34-5)26(36-28(29)33)20(4)15-19(3)25(31)24(14-17)35-6/h8-11,15-17,19,23-26,31H,7,12-14H2,1-6H3,(H2,29,33)(H,30,32)/b18-9+,20-15+/t17-,19+,23+,24+,25-,26+/m1/s1

> <INCHI_KEY>
VSRDDIXOACNXNB-DULVUOHVSA-N

> <FORMULA>
C28H42N2O6

> <MOLECULAR_WEIGHT>
502.652

> <EXACT_MASS>
502.30428708

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.66381952728339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.161400491820999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
1.688691692547744

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.701029066254855

> <JCHEM_PKA_STRONGEST_BASIC>
15.033707419872398

> <JCHEM_POLAR_SURFACE_AREA>
124.59000000000002

> <JCHEM_REFRACTIVITY>
154.4663

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      17.894  -1.275   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.701   0.253   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      16.281   0.849   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.961  -0.199   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.641  -1.705   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.109  -1.865   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.483  -0.458   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.596   0.606   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.975   0.294   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.710  -0.583   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      10.815   1.826   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.409   2.453   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.162   1.548   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.756   2.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.596   3.707   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.842   4.612   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.248   3.985   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.682   6.143   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.928   7.048   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.768   8.579   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.335   6.421   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.581   7.325   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.421   8.857   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.667   9.761   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.987   6.698   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.234   7.603   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.148   5.167   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.901   4.262   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.554   4.539   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.714   3.008   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.468   2.103   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.121   2.381   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.367   3.285   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      18.774   2.658   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      18.934   1.127   0.000  0.00  0.00           N+0
HETATM   36  O   UNK     0      20.020   3.563   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
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   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂N₂O₆

Average Mass

502.6520 Da

Monoisotopic Mass

502.30429 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1CC\C=C(C)\C(O)=NC2=CC=CC(C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)\C=C(C)\[C@@H]1OC(O)=N)=C2

InChI Identifier

InChI=1S/C28H42N2O6/c1-17-13-21-10-8-11-22(16-21)30-27(32)18(2)9-7-12-23(34-5)26(36-28(29)33)20(4)15-19(3)25(31)24(14-17)35-6/h8-11,15-17,19,23-26,31H,7,12-14H2,1-6H3,(H2,29,33)(H,30,32)/b18-9+,20-15+/t17-,19+,23+,24+,25-,26+/m1/s1

InChI Key

VSRDDIXOACNXNB-DULVUOHVSA-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
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

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

24694194

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24795078

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Poon AWC, Hofstaetter L, Judd-Lam S: Social connectedness of carers: An Australian national survey of carers. Health Soc Care Community. 2022 Sep 4. doi: 10.1111/hsc.13987. [PubMed:36057864 ]
Johnson-Laghi KA, Woo SM, Zafar Z, Fernandez S, Desale S, Robertazzi SE, Smith CI, Thomas AM, Lalos AT, Georgia SJ, Jenkins ML, Faust TW, Fishbein TM, Satoskar RS, Rangnekar AS, Hsu CC: Alcohol-associated liver disease predicts increased post-liver transplant opioid use. Clin Transplant. 2022 Sep 4:e14811. doi: 10.1111/ctr.14811. [PubMed:36057863 ]
Michael GC, Grema BA, Ashimi AO, Olawumi AL, Umar ZA, Mahmoud Z, Aji SA: Predictors of Satisfaction with Wound Care Services in an Outpatient Setting in Kano, Nigeria. West Afr J Med. 2022 Aug 31;39(8):800-807. [PubMed:36057862 ]
Jouglar E, Laprie A, Isfan F, Dumont B, Thebaud E, Escande A, Supiot S: Locoregional failure after postoperative flank irradiation for nephroblastoma: Results from the French cohort of the SIOP-2001 trial. Pediatr Blood Cancer. 2022 Sep 4:e29950. doi: 10.1002/pbc.29950. [PubMed:36057861 ]
Ruiu L, Marche MG, Mura ME, Tarasco E: Involvement of a novel Pseudomonas protegens strain associated with entomopathogenic nematode infective juveniles in insect pathogenesis. Pest Manag Sci. 2022 Sep 4. doi: 10.1002/ps.7166. [PubMed:36057860 ]
LOTUS database [Link]

Showing NP-Card for {[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid (NP0185377)

MOL for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D MOL for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D SDF for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D-SDF for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

PDB for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D PDB for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

SMILES for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

INCHI for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

Structure for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)

3D Structure for NP0185377 ({[(4e,8s,9s,10e,12s,13r,14s,16r)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-1(21),2,4,10,18(22),19-hexaen-9-yl]oxy}methanimidic acid)