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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:21:37 UTC

Update Date

2021-09-26 23:05:04 UTC

HMDB ID

HMDB0252468

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fosmidomycin

Description

Fosmidomycin belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Fosmidomycin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Fosmidomycin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fosmidomycin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fosmidomycin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(N-Hydroxyformamido)propylphosphonic acid	ChEBI
Fosmidomycina	ChEBI
Fosmidomycine	ChEBI
Fosmidomycinum	ChEBI
3-(N-Hydroxyformamido)propylphosphonate	Generator
3-(N-Formyl-N-hydroxy)aminopropylphosphonic acid	MeSH
Fosmidomycin monoammonium salt	MeSH
Fosmidomycin monopotassium salt	MeSH
Fosmidomycin sodium salt	MeSH
Fosfidomycin	MeSH
Fosmidomycin monosodium salt	MeSH
Fosmidomycin sodium	MeSH
Phosphonic acid, (3-(formylhydroxyamino)propyl)-, monosodium salt	MeSH

Chemical Formula

C₄H₁₀NO₅P

Average Molecular Weight

183.0997

Monoisotopic Molecular Weight

183.029658947

IUPAC Name

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

Traditional Name

fosmidomycin

CAS Registry Number

Not Available

SMILES

ON(CCCP(O)(O)=O)C=O

InChI Identifier

InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)

InChI Key

GJXWDTUCERCKIX-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

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

phosphonic acids (CHEBI:443725 )
hydroxamic acid (CHEBI:443725 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0252468)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-2.2	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	1.81	ChemAxon
pKa (Strongest Basic)	-5.6	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	36.83 m³·mol⁻¹	ChemAxon
Polarizability	15.06 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	129.26	30932474
DeepCCS	[M-H]-	126.145	30932474
DeepCCS	[M-2H]-	163.396	30932474
DeepCCS	[M+Na]+	138.337	30932474
AllCCS	[M+H]+	137.2	32859911
AllCCS	[M+H-H2O]+	133.5	32859911
AllCCS	[M+NH4]+	140.7	32859911
AllCCS	[M+Na]+	141.7	32859911
AllCCS	[M-H]-	131.1	32859911
AllCCS	[M+Na-2H]-	132.9	32859911
AllCCS	[M+HCOO]-	134.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fosmidomycin	ON(CCCP(O)(O)=O)C=O	2562.0	Standard polar	33892256
Fosmidomycin	ON(CCCP(O)(O)=O)C=O	1598.3	Standard non polar	33892256
Fosmidomycin	ON(CCCP(O)(O)=O)C=O	1791.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fosmidomycin,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCN(O)C=O	1830.8	Semi standard non polar	33892256
Fosmidomycin,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCN(O)C=O	1727.3	Standard non polar	33892256
Fosmidomycin,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCN(O)C=O	2750.8	Standard polar	33892256
Fosmidomycin,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCN(O)C=O)O[Si](C)(C)C	1868.8	Semi standard non polar	33892256
Fosmidomycin,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCN(O)C=O)O[Si](C)(C)C	1832.1	Standard non polar	33892256
Fosmidomycin,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCN(O)C=O)O[Si](C)(C)C	2228.2	Standard polar	33892256
Fosmidomycin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCN(O)C=O	2073.7	Semi standard non polar	33892256
Fosmidomycin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCN(O)C=O	1977.0	Standard non polar	33892256
Fosmidomycin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCN(O)C=O	2797.0	Standard polar	33892256
Fosmidomycin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCN(O)C=O)O[Si](C)(C)C(C)(C)C	2346.9	Semi standard non polar	33892256
Fosmidomycin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCN(O)C=O)O[Si](C)(C)C(C)(C)C	2301.1	Standard non polar	33892256
Fosmidomycin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCN(O)C=O)O[Si](C)(C)C(C)(C)C	2403.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fosmidomycin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-9500000000-efefa3a227a7b5c7f124	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fosmidomycin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 10V, Positive-QTOF	splash10-001i-1900000000-efff9b2b102da3770ca1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 20V, Positive-QTOF	splash10-00e9-4900000000-e029528c2811bd757b79	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 40V, Positive-QTOF	splash10-0006-9100000000-4eeab8edda51c4a8f8c5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 10V, Negative-QTOF	splash10-001i-4900000000-9f2329d74cd801da12e2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 20V, Negative-QTOF	splash10-03e9-9500000000-a5dd0804c50f3b3f9dc4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 40V, Negative-QTOF	splash10-004i-9000000000-a479146ddc009fae71c8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 10V, Positive-QTOF	splash10-014i-0900000000-cad94378253cc0a48814	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 20V, Positive-QTOF	splash10-0239-9200000000-6ecf858c506536d25149	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 40V, Positive-QTOF	splash10-001i-9000000000-8c9ec18716c3ac58921d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 10V, Negative-QTOF	splash10-001i-0900000000-468bbe7a5932e8fea31e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 20V, Negative-QTOF	splash10-0gy9-7900000000-7a0e8dffd22fca86a2c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosmidomycin 40V, Negative-QTOF	splash10-004i-9000000000-767fc30363df3b107e08	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02948

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00018263

Chemspider ID

555

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fosmidomycin

METLIN ID

Not Available

PubChem Compound

572

PDB ID

Not Available

ChEBI ID

443725

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Fosmidomycin (HMDB0252468)

MOL for HMDB0252468 (Fosmidomycin)

3D MOL for HMDB0252468 (Fosmidomycin)

3D SDF for HMDB0252468 (Fosmidomycin)

3D-SDF for HMDB0252468 (Fosmidomycin)

PDB for HMDB0252468 (Fosmidomycin)

3D PDB for HMDB0252468 (Fosmidomycin)

SMILES for HMDB0252468 (Fosmidomycin)

INCHI for HMDB0252468 (Fosmidomycin)

Structure for HMDB0252468 (Fosmidomycin)

3D Structure for HMDB0252468 (Fosmidomycin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra