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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:57:37 UTC

Update Date

2021-09-26 23:12:08 UTC

HMDB ID

HMDB0256474

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phosphocysteamine

Description

Phosphocysteamine, also known as cistafos or cystaphos, belongs to the class of organic compounds known as organothiophosphorus compounds. These are organic derivatives of thiophosphonic acid, thiophosphoric acid, dithiophosphoric acid, or phosphorotrithioic acid, or derivatives thereof. Thiophosphonic acid, dithiophosphoric acid, thiophosphoric acid, and phosphorotrithioic acid are thiophosphorus compounds with the formula OP(O)(=S), OP(S)(=S)O, OP(O)(=S)O, and OP(=S)(S)S, respectively. Based on a literature review a significant number of articles have been published on Phosphocysteamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phosphocysteamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phosphocysteamine 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
2-Aminoethanethiol dihydrogen phosphate	ChEBI
S-(2-Aminoethyl) phosphorothioate	ChEBI
S-Phosphocysteamine	ChEBI
2-Aminoethanethiol dihydrogen phosphoric acid	Generator
S-(2-Aminoethyl) phosphorothioic acid	Generator
Cysteamine S-phosphoric acid	HMDB
Cistafos	HMDB
Cistaphos	HMDB
Cystafos	HMDB
Cystaphos	HMDB
Salt beta-aminoethylthiophosphate, sodium	HMDB
Sodium salt beta-aminoethylthiophosphate	HMDB
beta Aminoethylthiophosphate, sodium salt	HMDB
beta-Aminoethylthiophosphate, sodium salt	HMDB
Phosphocysteamine	ChEBI

Chemical Formula

C₂H₈NO₃PS

Average Molecular Weight

157.12

Monoisotopic Molecular Weight

156.996251294

IUPAC Name

[(2-aminoethyl)sulfanyl]phosphonic acid

Traditional Name

(2-aminoethyl)sulfanylphosphonic acid

CAS Registry Number

Not Available

SMILES

NCCSP(O)(O)=O

InChI Identifier

InChI=1S/C2H8NO3PS/c3-1-2-8-7(4,5)6/h1-3H2,(H2,4,5,6)

InChI Key

RZPNFYXFSHGGBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organothiophosphorus compounds. These are organic derivatives of thiophosphonic acid, thiophosphoric acid, dithiophosphoric acid, or phosphorotrithioic acid, or derivatives thereof. Thiophosphonic acid, dithiophosphoric acid, thiophosphoric acid, and phosphorotrithioic acid are thiophosphorus compounds with the formula OP(O)(=S), OP(S)(=S)O, OP(O)(=S)O, and OP(=S)(S)S, respectively.

Kingdom

Organic compounds

Super Class

Organophosphorus compounds

Class

Organothiophosphorus compounds

Sub Class

Not Available

Direct Parent

Organothiophosphorus compounds

Alternative Parents

Substituents

Sulfenyl compound
Organothiophosphorus compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:74951 )
primary amino compound (CHEBI:74951 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	-1.5	ALOGPS
logP	-2.2	ChemAxon
logS	-0.57	ALOGPS
pKa (Strongest Acidic)	2.05	ChemAxon
pKa (Strongest Basic)	10.47	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	33.69 m³·mol⁻¹	ChemAxon
Polarizability	13.17 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]+	130.547	30932474
DeepCCS	[M-H]-	127.747	30932474
DeepCCS	[M-2H]-	164.041	30932474
DeepCCS	[M+Na]+	138.555	30932474
AllCCS	[M+H]+	132.7	32859911
AllCCS	[M+H-H2O]+	128.9	32859911
AllCCS	[M+NH4]+	136.3	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	133.6	32859911
AllCCS	[M+Na-2H]-	137.0	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phosphocysteamine	NCCSP(O)(O)=O	2314.9	Standard polar	33892256
Phosphocysteamine	NCCSP(O)(O)=O	1472.3	Standard non polar	33892256
Phosphocysteamine	NCCSP(O)(O)=O	1657.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phosphocysteamine,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)SCCN	1574.2	Semi standard non polar	33892256
Phosphocysteamine,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)SCCN	1488.2	Standard non polar	33892256
Phosphocysteamine,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)SCCN	2484.4	Standard polar	33892256
Phosphocysteamine,1TMS,isomer #2	C[Si](C)(C)NCCSP(=O)(O)O	1692.5	Semi standard non polar	33892256
Phosphocysteamine,1TMS,isomer #2	C[Si](C)(C)NCCSP(=O)(O)O	1547.0	Standard non polar	33892256
Phosphocysteamine,1TMS,isomer #2	C[Si](C)(C)NCCSP(=O)(O)O	2644.1	Standard polar	33892256
Phosphocysteamine,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)SCCN	1639.0	Semi standard non polar	33892256
Phosphocysteamine,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)SCCN	1610.0	Standard non polar	33892256
Phosphocysteamine,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)SCCN	2112.9	Standard polar	33892256
Phosphocysteamine,2TMS,isomer #2	C[Si](C)(C)NCCSP(=O)(O)O[Si](C)(C)C	1712.1	Semi standard non polar	33892256
Phosphocysteamine,2TMS,isomer #2	C[Si](C)(C)NCCSP(=O)(O)O[Si](C)(C)C	1675.2	Standard non polar	33892256
Phosphocysteamine,2TMS,isomer #2	C[Si](C)(C)NCCSP(=O)(O)O[Si](C)(C)C	2109.3	Standard polar	33892256
Phosphocysteamine,2TMS,isomer #3	C[Si](C)(C)N(CCSP(=O)(O)O)[Si](C)(C)C	1828.1	Semi standard non polar	33892256
Phosphocysteamine,2TMS,isomer #3	C[Si](C)(C)N(CCSP(=O)(O)O)[Si](C)(C)C	1809.1	Standard non polar	33892256
Phosphocysteamine,2TMS,isomer #3	C[Si](C)(C)N(CCSP(=O)(O)O)[Si](C)(C)C	2543.9	Standard polar	33892256
Phosphocysteamine,3TMS,isomer #1	C[Si](C)(C)NCCSP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1762.7	Semi standard non polar	33892256
Phosphocysteamine,3TMS,isomer #1	C[Si](C)(C)NCCSP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1772.3	Standard non polar	33892256
Phosphocysteamine,3TMS,isomer #1	C[Si](C)(C)NCCSP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1811.6	Standard polar	33892256
Phosphocysteamine,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)SCCN([Si](C)(C)C)[Si](C)(C)C	1878.4	Semi standard non polar	33892256
Phosphocysteamine,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)SCCN([Si](C)(C)C)[Si](C)(C)C	1892.9	Standard non polar	33892256
Phosphocysteamine,3TMS,isomer #2	C[Si](C)(C)OP(=O)(O)SCCN([Si](C)(C)C)[Si](C)(C)C	2064.6	Standard polar	33892256
Phosphocysteamine,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)SCCN([Si](C)(C)C)[Si](C)(C)C	1912.2	Semi standard non polar	33892256
Phosphocysteamine,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)SCCN([Si](C)(C)C)[Si](C)(C)C	1936.9	Standard non polar	33892256
Phosphocysteamine,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)SCCN([Si](C)(C)C)[Si](C)(C)C	1831.4	Standard polar	33892256
Phosphocysteamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)SCCN	1810.6	Semi standard non polar	33892256
Phosphocysteamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)SCCN	1715.4	Standard non polar	33892256
Phosphocysteamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)SCCN	2575.0	Standard polar	33892256
Phosphocysteamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCSP(=O)(O)O	1929.9	Semi standard non polar	33892256
Phosphocysteamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCSP(=O)(O)O	1783.2	Standard non polar	33892256
Phosphocysteamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCSP(=O)(O)O	2767.8	Standard polar	33892256
Phosphocysteamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)SCCN	2127.2	Semi standard non polar	33892256
Phosphocysteamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)SCCN	2035.3	Standard non polar	33892256
Phosphocysteamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)SCCN	2265.0	Standard polar	33892256
Phosphocysteamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCSP(=O)(O)O[Si](C)(C)C(C)(C)C	2192.0	Semi standard non polar	33892256
Phosphocysteamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCSP(=O)(O)O[Si](C)(C)C(C)(C)C	2134.9	Standard non polar	33892256
Phosphocysteamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCSP(=O)(O)O[Si](C)(C)C(C)(C)C	2341.8	Standard polar	33892256
Phosphocysteamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCSP(=O)(O)O)[Si](C)(C)C(C)(C)C	2275.8	Semi standard non polar	33892256
Phosphocysteamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCSP(=O)(O)O)[Si](C)(C)C(C)(C)C	2225.2	Standard non polar	33892256
Phosphocysteamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCSP(=O)(O)O)[Si](C)(C)C(C)(C)C	2642.0	Standard polar	33892256
Phosphocysteamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCSP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2418.5	Semi standard non polar	33892256
Phosphocysteamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCSP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2359.9	Standard non polar	33892256
Phosphocysteamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCSP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2188.1	Standard polar	33892256
Phosphocysteamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)SCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2555.4	Semi standard non polar	33892256
Phosphocysteamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)SCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2490.6	Standard non polar	33892256
Phosphocysteamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)SCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2363.8	Standard polar	33892256
Phosphocysteamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)SCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2781.9	Semi standard non polar	33892256
Phosphocysteamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)SCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2649.0	Standard non polar	33892256
Phosphocysteamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)SCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2259.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphocysteamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-7fe573b68421f702743d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphocysteamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2813

KEGG Compound ID

Not Available

BioCyc ID

CPD-3721

BiGG ID

Not Available

Wikipedia Link

Cysteamine

METLIN ID

Not Available

PubChem Compound

2916

PDB ID

Not Available

ChEBI ID

74951

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 Phosphocysteamine (HMDB0256474)

MOL for HMDB0256474 (Phosphocysteamine)

3D MOL for HMDB0256474 (Phosphocysteamine)

3D SDF for HMDB0256474 (Phosphocysteamine)

3D-SDF for HMDB0256474 (Phosphocysteamine)

PDB for HMDB0256474 (Phosphocysteamine)

3D PDB for HMDB0256474 (Phosphocysteamine)

SMILES for HMDB0256474 (Phosphocysteamine)

INCHI for HMDB0256474 (Phosphocysteamine)

Structure for HMDB0256474 (Phosphocysteamine)

3D Structure for HMDB0256474 (Phosphocysteamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

NMR Spectra