NP-MRD: Showing NP-Card for Antibiotic TAN 585D (NP0061925)

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Record Information

Version

2.0

Created at

2022-04-28 06:36:54 UTC

Updated at

2022-04-28 06:36:54 UTC

NP-MRD ID

NP0061925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Antibiotic TAN 585D

Description

(2R)-2-amino-4-{4-[(R)-{[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-C-hydroxycarbonimidoyl}[(hydroxymethylidene)amino]methyl]phenoxy}butanoic acid 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. Antibiotic TAN 585D is found in Flexibacter alginoliquefaciens sp. nov. YK-49. Based on a literature review very few articles have been published on (2R)-2-amino-4-{4-[(R)-{[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-C-hydroxycarbonimidoyl}[(hydroxymethylidene)amino]methyl]phenoxy}butanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208362D          

 37 39  0  0  1  0            999 V2000
   -0.0749   -1.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4874   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7501    0.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1626   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -1.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1626    0.9265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4001    1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2251    1.6410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6376    0.9265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376    2.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2251    3.0699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1626   -3.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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 34  6  1  0
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M  END


  Mrv1652304282208362D          

 37 39  0  0  1  0            999 V2000
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    3.6376    0.9265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  2  0  0  0  0
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 24 32  1  6  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 15 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0061925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H](CCOC1=CC=C(C=C1)[C@@H](NC=O)C(=O)N[C@H]1CN([C@@H](C(O)=O)C2=CC=C(O)C=C2)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26N4O9/c25-17(23(33)34)9-10-37-16-7-3-13(4-8-16)19(26-12-29)21(31)27-18-11-28(22(18)32)20(24(35)36)14-1-5-15(30)6-2-14/h1-8,12,17-20,30H,9-11,25H2,(H,26,29)(H,27,31)(H,33,34)(H,35,36)/t17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
IQYXUENJMSFELH-IYWMVGAKSA-N

> <FORMULA>
C24H26N4O9

> <MOLECULAR_WEIGHT>
514.491

> <EXACT_MASS>
514.169978433

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.28846030900236

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-4-{4-[(R)-{[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}(formamido)methyl]phenoxy}butanoic acid

> <ALOGPS_LOGP>
-0.17

> <JCHEM_LOGP>
-3.4046575033119573

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.329033848415093

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.877470959428842

> <JCHEM_PKA_STRONGEST_BASIC>
9.055135226825852

> <JCHEM_POLAR_SURFACE_AREA>
208.58999999999997

> <JCHEM_REFRACTIVITY>
125.04169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-4-{4-[(R)-{[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}(formamido)methyl]phenoxy}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.140  -2.272   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.910  -0.938   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.140   0.396   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.400   0.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.170  -0.938   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.400  -2.272   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.170   1.729   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.710   1.729   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.480   3.063   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.020   3.063   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.790   1.729   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.790   4.397   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.330   4.397   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.020   5.730   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.910  -3.605   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.450  -3.605   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.220  -2.272   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -3.220  -4.939   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -4.760  -4.939   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.849  -6.028   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -6.938  -4.939   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -5.849  -3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.849  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.478  -4.939   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.248  -6.273   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.478  -7.606   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.248  -8.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -10.788  -8.940   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.558  -7.606   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.788  -6.273   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -11.558 -10.274   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -9.248  -3.605   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -10.788  -3.605   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -8.478  -2.272   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0      -0.140  -4.939   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       1.400  -4.939   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.170  -6.273   0.000  0.00  0.00           O+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1   16   35                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   19   23                                                  
CONECT   23   22                                                            
CONECT   24   21   25   32                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28                                                            
CONECT   32   24   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   15   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-Amino-4-{4-[(R)-{[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-C-hydroxycarbonimidoyl}[(hydroxymethylidene)amino]methyl]phenoxy}butanoate	Generator

Chemical Formula

C₂₄H₂₆N₄O₉

Average Mass

514.4910 Da

Monoisotopic Mass

514.16998 Da

IUPAC Name

(2R)-2-amino-4-{4-[(R)-{[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}(formamido)methyl]phenoxy}butanoic acid

Traditional Name

(2R)-2-amino-4-{4-[(R)-{[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}(formamido)methyl]phenoxy}butanoic acid

CAS Registry Number

Not Available

SMILES

N[C@H](CCOC1=CC=C(C=C1)[C@@H](NC=O)C(=O)N[C@H]1CN([C@@H](C(O)=O)C2=CC=C(O)C=C2)C1=O)C(O)=O

InChI Identifier

InChI=1S/C24H26N4O9/c25-17(23(33)34)9-10-37-16-7-3-13(4-8-16)19(26-12-29)21(31)27-18-11-28(22(18)32)20(24(35)36)14-1-5-15(30)6-2-14/h1-8,12,17-20,30H,9-11,25H2,(H,26,29)(H,27,31)(H,33,34)(H,35,36)/t17-,18+,19-,20-/m1/s1

InChI Key

IQYXUENJMSFELH-IYWMVGAKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Flexibacter alginoliquefaciens sp. nov. YK-49	Bacteria	KNApSAcK

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
Monobactam
N-acyl-alpha amino acid or derivatives
N-formyl-alpha amino acid or derivatives
N-formyl-alpha-amino acid
Alpha-amino acid amide
Phenylacetamide
Alpha-amino acid
D-alpha-amino acid
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Phenol ether
Phenoxy compound
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Beta-lactam
Tertiary carboxylic acid amide
Amino acid
Secondary carboxylic acid amide
Amino acid or derivatives
Azetidine
Lactam
Carboxamide group
Organoheterocyclic compound
Ether
Azacycle
Carboxylic acid
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Amine
Primary amine
Organic oxide
Organopnictogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-0.17	ALOGPS
logP	-3.4	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	208.59 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	125.04 m³·mol⁻¹	ChemAxon
Polarizability	51.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

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

163008829

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Antibiotic TAN 585D (NP0061925)

MOL for NP0061925 (Antibiotic TAN 585D)

3D MOL for NP0061925 (Antibiotic TAN 585D)

3D SDF for NP0061925 (Antibiotic TAN 585D)

3D-SDF for NP0061925 (Antibiotic TAN 585D)

PDB for NP0061925 (Antibiotic TAN 585D)

3D PDB for NP0061925 (Antibiotic TAN 585D)

SMILES for NP0061925 (Antibiotic TAN 585D)

INCHI for NP0061925 (Antibiotic TAN 585D)

Structure for NP0061925 (Antibiotic TAN 585D)

3D Structure for NP0061925 (Antibiotic TAN 585D)