NP-MRD: Showing NP-Card for (2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid (NP0227053)

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Record Information

Version

2.0

Created at

2022-09-06 06:16:29 UTC

Updated at

2022-09-06 06:16:29 UTC

NP-MRD ID

NP0227053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid

Description

(2R)-3-{[(1Z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid belongs to the class of organic compounds known as s-alkyl-thiohydroximates. These are organosulfur compounds with the general structure RC(S)=NOH, where R =alkyl group. (2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid is found in Streptomyces regensis. Based on a literature review very few articles have been published on (2R)-3-{[(1Z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 31  0  0  0  0  0  0  0  0999 V2000
    4.8953    1.2198   -0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900    0.9767   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    1.8158    0.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8114    0.0087   -0.5902 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5341   -0.2095    0.0690 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8967   -1.4022   -0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7006   -1.8399    0.0457 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156   -0.7267   -0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    0.1776   -1.2141 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877    0.4110   -1.9804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3042   -0.9281    0.4281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0098   -0.7955    1.7809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5709    0.2171   -0.1222 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.3613   -0.4344   -1.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6683    0.5005    1.1284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979    1.6892   -0.6356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8063   -0.5027    1.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8327   -0.7193    2.2529 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0976   -0.5304    1.9832 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7747    1.7547   -1.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3694    0.2287   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5338    1.8174   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824    2.2428    1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015    0.6672    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5806   -2.2826   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -1.2030   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8711    0.7886   -2.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6231   -1.9663    0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    0.1205    2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8131   -0.3238    1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3100    2.0037   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5732   -1.3857    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 15  1  0
 13 16  1  0
 13 14  2  0
  5 17  1  0
 17 19  1  0
 17 18  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  1
  6 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
M  END


  Mrv1652309062208162D          

 19 18  0  0  1  0            999 V2000
    2.6664    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -1.7605    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=N[C@@H](CS\C(=N/O)C(O)P(O)(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13N2O8PS/c1-3(10)8-4(6(11)12)2-19-5(9-14)7(13)18(15,16)17/h4,7,13-14H,2H2,1H3,(H,8,10)(H,11,12)(H2,15,16,17)/b9-5-/t4-,7?/m0/s1

> <INCHI_KEY>
FZWZNRYXWVCQFM-UWXFRZKFSA-N

> <FORMULA>
C7H13N2O8PS

> <MOLECULAR_WEIGHT>
316.22

> <EXACT_MASS>
316.013023559

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.41805125026371

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-{[(1Z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid

> <JCHEM_LOGP>
-2.065705665993235

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.5348215811060846

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2930771269974581

> <JCHEM_PKA_STRONGEST_BASIC>
0.5432706840153805

> <JCHEM_POLAR_SURFACE_AREA>
180.24

> <JCHEM_REFRACTIVITY>
63.667300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-{[(1Z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.977   5.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.977   4.414   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       2.310  -0.206   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       0.976  -0.976   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.357  -0.206   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.976  -2.516   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.357  -3.286   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0       2.310  -3.286   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0       3.644  -4.056   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.540  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.080  -1.953   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
(2R)-3-{[(1Z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoate	Generator
(2R)-3-{[(1Z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulphanyl}-2-[(1-hydroxyethylidene)amino]propanoate	Generator
(2R)-3-{[(1Z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulphanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid	Generator

Chemical Formula

C₇H₁₃N₂O₈PS

Average Mass

316.2200 Da

Monoisotopic Mass

316.01302 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(O)=N[C@@H](CS\C(=N/O)C(O)P(O)(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H13N2O8PS/c1-3(10)8-4(6(11)12)2-19-5(9-14)7(13)18(15,16)17/h4,7,13-14H,2H2,1H3,(H,8,10)(H,11,12)(H2,15,16,17)/b9-5-/t4-,7?/m0/s1

InChI Key

FZWZNRYXWVCQFM-UWXFRZKFSA-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 regensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as s-alkyl-thiohydroximates. These are organosulfur compounds with the general structure RC(S)=NOH, where R =alkyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Thiohydroximic acids and derivatives

Sub Class

Thiohydroximic acids

Direct Parent

S-alkyl-thiohydroximates

Alternative Parents

Substituents

S-alkyl-thiohydroximate
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid or derivatives
Fatty acid
Organophosphonic acid derivative
Organophosphonic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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

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

138970710

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid (NP0227053)

MOL for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

3D MOL for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

3D SDF for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

3D-SDF for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

PDB for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

3D PDB for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

SMILES for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

INCHI for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

Structure for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)

3D Structure for NP0227053 ((2r)-3-{[(1z)-2-hydroxy-1-(hydroxyimino)-2-phosphonoethyl]sulfanyl}-2-[(1-hydroxyethylidene)amino]propanoic acid)