NP-MRD: Showing NP-Card for FR-900098 (NP0021946)

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Record Information

Version

2.0

Created at

2021-01-06 07:11:19 UTC

Updated at

2021-07-15 17:37:43 UTC

NP-MRD ID

NP0021946

Secondary Accession Numbers

None

Natural Product Identification

Common Name

FR-900098

Provided By

NPAtlas

Description

FR-900098 is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. FR-900098 is found in Streptomyces and Streptomyces rubellomurinus. FR-900098 was first documented in 1980 (PMID: 6768704). Based on a literature review a small amount of articles have been published on FR-900098 (PMID: 31451762) (PMID: 30783866) (PMID: 30681110).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105203D          

 24 23  0  0  0  0            999 V2000
    3.5462    0.6733    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4545    0.8156   -0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094    1.9363   -0.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6086   -0.2825   -0.6408 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8263   -1.4488   -0.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123   -0.2313   -1.5785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7751    0.1865   -0.9439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2373   -0.7195    0.1506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8077   -0.0471    0.7911 P   0  0  1  0  0  5  0  0  0  0  0  0
   -2.7571    0.1020    2.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1115    1.4954    0.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1125   -1.0345    0.3285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8706   -0.3756    0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4467    1.2197    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766    1.0629    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205   -1.2902    0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3679   -1.1797   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768    0.5408   -2.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561    0.1803   -1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159    1.2150   -0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5325   -0.7584    1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971   -1.7610   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0654    1.6799    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8483   -1.9791    0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  5 16  1  0  0  0  0
  6 17  1  0  0  0  0
  6 18  1  0  0  0  0
  7 19  1  0  0  0  0
  7 20  1  0  0  0  0
  8 21  1  0  0  0  0
  8 22  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021946

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]ON(C(=O)C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[P](=O)(O[H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C5H12NO5P/c1-5(7)6(8)3-2-4-12(9,10)11/h8H,2-4H2,1H3,(H2,9,10,11)

> <INCHI_KEY>
PKMNDDZSIHLLLI-UHFFFAOYSA-N

> <FORMULA>
C5H12NO5P

> <MOLECULAR_WEIGHT>
197.1262

> <EXACT_MASS>
197.045309011

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.134884677948627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3-(N-hydroxyacetamido)propyl]phosphonic acid

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-2.1551654839999994

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.046365650272053

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8097414153953446

> <JCHEM_PKA_STRONGEST_BASIC>
-5.683545688566054

> <JCHEM_POLAR_SURFACE_AREA>
98.07000000000001

> <JCHEM_REFRACTIVITY>
41.3254

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(N-hydroxyacetamido)propylphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.546   0.673   0.606  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.454   0.816  -0.364  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.309   1.936  -0.926  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.609  -0.283  -0.641  0.00  0.00           N+0
HETATM    5  O   UNK     0       1.826  -1.449  -0.001  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.512  -0.231  -1.579  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.775   0.187  -0.944  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.237  -0.720   0.151  0.00  0.00           C+0
HETATM    9  P   UNK     0      -2.808  -0.047   0.791  0.00  0.00           P+0
HETATM   10  O   UNK     0      -2.757   0.102   2.302  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.111   1.495   0.140  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.112  -1.034   0.329  0.00  0.00           O+0
HETATM   13  H   UNK     0       3.871  -0.376   0.765  0.00  0.00           H+0
HETATM   14  H   UNK     0       4.447   1.220   0.248  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.277   1.063   1.613  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.921  -1.290   0.979  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.368  -1.180  -2.127  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.777   0.541  -2.336  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.556   0.180  -1.737  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.716   1.215  -0.533  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.533  -0.758   1.007  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.397  -1.761  -0.172  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.065   1.680   0.049  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.848  -1.979   0.505  0.00  0.00           H+0
CONECT    1    2   13   14   15                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4   16                                                       
CONECT    6    4    7   17   18                                             
CONECT    7    6    8   19   20                                             
CONECT    8    7    9   21   22                                             
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9   23                                                       
CONECT   12    9   24                                                       
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    5                                                            
CONECT   17    6                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    7                                                            
CONECT   21    8                                                            
CONECT   22    8                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3-(Acetylhydroxyamino)propyl)phosphonic acid	Kegg
(3-(Acetylhydroxyamino)propyl)phosphonate	Generator
3-(N-Acetyl-N-hydroxy)aminopropylphosphonic acid	MeSH
[3-(N-Hydroxyacetamido)propyl]phosphonate	Generator

Chemical Formula

C₅H₁₂NO₅P

Average Mass

197.1262 Da

Monoisotopic Mass

197.04531 Da

IUPAC Name

[3-(N-hydroxyacetamido)propyl]phosphonic acid

Traditional Name

3-(N-hydroxyacetamido)propylphosphonic acid

CAS Registry Number

Not Available

SMILES

CC(=O)N(O)CCCP(O)(O)=O

InChI Identifier

InChI=1S/C5H12NO5P/c1-5(7)6(8)3-2-4-12(9,10)11/h8H,2-4H2,1H3,(H2,9,10,11)

InChI Key

PKMNDDZSIHLLLI-UHFFFAOYSA-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
Streptomyces	NPAtlas	6768704
Streptomyces rubellomurinus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces rubellomurinus sp. nov. ATCC 31215	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Organic phosphonic acids

Direct Parent

Organic phosphonic acids

Alternative Parents

Substituents

Acetohydroxamic acid
Acetamide
Organophosphonic acid
Hydroxamic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphonoacetic acid (CHEBI:81398 )

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	ALOGPS
logP	-2.2	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	1.81	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	98.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.33 m³·mol⁻¹	ChemAxon
Polarizability	17.13 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA007537

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018262

Chemspider ID

142443

KEGG Compound ID

C17942

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162204

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Okuhara M, Kuroda Y, Goto T, Okamoto M, Terano H, Kohsaka M, Aoki H, Imanaka H: Studies on new phosphonic acid antibiotics. I. FR-900098, isolation and characterization. J Antibiot (Tokyo). 1980 Jan;33(1):13-7. doi: 10.7164/antibiotics.33.13. [PubMed:6768704 ]
Parkinson EI, Erb A, Eliot AC, Ju KS, Metcalf WW: Fosmidomycin biosynthesis diverges from related phosphonate natural products. Nat Chem Biol. 2019 Nov;15(11):1049-1056. doi: 10.1038/s41589-019-0343-1. Epub 2019 Aug 26. [PubMed:31451762 ]
Chellapandi P, Prathiviraj R, Prisilla A: Deciphering structure, function and mechanism of Plasmodium IspD homologs from their evolutionary imprints. J Comput Aided Mol Des. 2019 Apr;33(4):419-436. doi: 10.1007/s10822-019-00191-2. Epub 2019 Feb 19. [PubMed:30783866 ]
Nguyen K, DeSieno MA, Bae B, Johannes TW, Cobb RE, Zhao H, Nair SK: Characterization of the flavin monooxygenase involved in biosynthesis of the antimalarial FR-900098. Org Biomol Chem. 2019 Feb 6;17(6):1506-1518. doi: 10.1039/c8ob02840k. [PubMed:30681110 ]

Showing NP-Card for FR-900098 (NP0021946)

MOL for NP0021946 (FR-900098)

3D MOL for NP0021946 (FR-900098)

3D SDF for NP0021946 (FR-900098)

3D-SDF for NP0021946 (FR-900098)

PDB for NP0021946 (FR-900098)

3D PDB for NP0021946 (FR-900098)

SMILES for NP0021946 (FR-900098)

INCHI for NP0021946 (FR-900098)

Structure for NP0021946 (FR-900098)

3D Structure for NP0021946 (FR-900098)