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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:22:54 UTC

Update Date

2021-09-26 22:51:48 UTC

HMDB ID

HMDB0244204

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,4-Butanediphosphonic acid

Description

1,4-Butanediphosphonic acid, also known as (4-phosphonobutyl)phosphonate, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Based on a literature review a small amount of articles have been published on 1,4-Butanediphosphonic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,4-butanediphosphonic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,4-Butanediphosphonic acid 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

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.127  -4.620   0.000  0.00  0.00           C+0
HETATM    4  P   UNK     0      -1.127  -6.160   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      -1.127  -7.700   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.413  -6.160   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.667  -6.160   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    9  P   UNK     0       1.540   0.000   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       1.540   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.080  -0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,4-Butanediphosphonate	Generator
(4-Phosphonobutyl)phosphonate	HMDB

Chemical Formula

C₄H₁₂O₆P₂

Average Molecular Weight

218.082

Monoisotopic Molecular Weight

218.010912102

IUPAC Name

(4-phosphonobutyl)phosphonic acid

Traditional Name

4-phosphonobutylphosphonic acid

CAS Registry Number

Not Available

SMILES

OP(O)(=O)CCCCP(O)(O)=O

InChI Identifier

InChI=1S/C4H12O6P2/c5-11(6,7)3-1-2-4-12(8,9)10/h1-4H2,(H2,5,6,7)(H2,8,9,10)

InChI Key

JKTORXLUQLQJCM-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
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-0.55	ALOGPS
logP	-2	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.14 m³·mol⁻¹	ChemAxon
Polarizability	17.43 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]+	113.101	30932474
DeepCCS	[M-H]-	109.34	30932474
DeepCCS	[M-2H]-	147.038	30932474
DeepCCS	[M+Na]+	122.368	30932474
AllCCS	[M+H]+	142.8	32859911
AllCCS	[M+H-H2O]+	139.3	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.1	32859911
AllCCS	[M-H]-	135.8	32859911
AllCCS	[M+Na-2H]-	137.3	32859911
AllCCS	[M+HCOO]-	138.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4-Butanediphosphonic acid	OP(O)(=O)CCCCP(O)(O)=O	3118.0	Standard polar	33892256
1,4-Butanediphosphonic acid	OP(O)(=O)CCCCP(O)(O)=O	1758.0	Standard non polar	33892256
1,4-Butanediphosphonic acid	OP(O)(=O)CCCCP(O)(O)=O	2133.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,4-Butanediphosphonic acid,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O	2080.0	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O	1924.5	Standard non polar	33892256
1,4-Butanediphosphonic acid,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O	3008.3	Standard polar	33892256
1,4-Butanediphosphonic acid,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCCP(=O)(O)O)O[Si](C)(C)C	2115.2	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCCP(=O)(O)O)O[Si](C)(C)C	2047.6	Standard non polar	33892256
1,4-Butanediphosphonic acid,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCCP(=O)(O)O)O[Si](C)(C)C	2589.4	Standard polar	33892256
1,4-Butanediphosphonic acid,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O[Si](C)(C)C	2136.8	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O[Si](C)(C)C	2012.6	Standard non polar	33892256
1,4-Butanediphosphonic acid,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O[Si](C)(C)C	2563.8	Standard polar	33892256
1,4-Butanediphosphonic acid,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2136.7	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2076.2	Standard non polar	33892256
1,4-Butanediphosphonic acid,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CCCCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2310.7	Standard polar	33892256
1,4-Butanediphosphonic acid,4TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2140.3	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,4TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2112.4	Standard non polar	33892256
1,4-Butanediphosphonic acid,4TMS,isomer #1	C[Si](C)(C)OP(=O)(CCCCP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2128.2	Standard polar	33892256
1,4-Butanediphosphonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O	2315.0	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O	2149.0	Standard non polar	33892256
1,4-Butanediphosphonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O	3118.2	Standard polar	33892256
1,4-Butanediphosphonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCCP(=O)(O)O)O[Si](C)(C)C(C)(C)C	2586.1	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCCP(=O)(O)O)O[Si](C)(C)C(C)(C)C	2479.1	Standard non polar	33892256
1,4-Butanediphosphonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCCP(=O)(O)O)O[Si](C)(C)C(C)(C)C	2778.5	Standard polar	33892256
1,4-Butanediphosphonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O[Si](C)(C)C(C)(C)C	2577.2	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O[Si](C)(C)C(C)(C)C	2482.9	Standard non polar	33892256
1,4-Butanediphosphonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O)O[Si](C)(C)C(C)(C)C	2728.1	Standard polar	33892256
1,4-Butanediphosphonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2784.1	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2670.9	Standard non polar	33892256
1,4-Butanediphosphonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CCCCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2551.3	Standard polar	33892256
1,4-Butanediphosphonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2978.8	Semi standard non polar	33892256
1,4-Butanediphosphonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2734.8	Standard non polar	33892256
1,4-Butanediphosphonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CCCCP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2475.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4-Butanediphosphonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-8920000000-096a7c87dbb5cb879dbe	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4-Butanediphosphonic acid 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 - 1,4-Butanediphosphonic acid 10V, Positive-QTOF	splash10-0uxr-0690000000-579c73c79525d77dd0fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediphosphonic acid 20V, Positive-QTOF	splash10-052r-8900000000-90a10e391cda974b8af3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediphosphonic acid 40V, Positive-QTOF	splash10-053r-9000000000-91dfdb8420445771ca05	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediphosphonic acid 10V, Negative-QTOF	splash10-014i-0090000000-6ae2baabedc6397dc3ca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediphosphonic acid 20V, Negative-QTOF	splash10-014i-2390000000-eaf8da7a962eb7848249	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Butanediphosphonic acid 40V, Negative-QTOF	splash10-004i-9000000000-189cd2febe5efb14a72a	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	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

386608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

437082

PDB ID

Not Available

ChEBI ID

Not Available

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 1,4-Butanediphosphonic acid (HMDB0244204)

MOL for HMDB0244204 (1,4-Butanediphosphonic acid)

3D MOL for HMDB0244204 (1,4-Butanediphosphonic acid)

3D SDF for HMDB0244204 (1,4-Butanediphosphonic acid)

3D-SDF for HMDB0244204 (1,4-Butanediphosphonic acid)

PDB for HMDB0244204 (1,4-Butanediphosphonic acid)

3D PDB for HMDB0244204 (1,4-Butanediphosphonic acid)

SMILES for HMDB0244204 (1,4-Butanediphosphonic acid)

INCHI for HMDB0244204 (1,4-Butanediphosphonic acid)

Structure for HMDB0244204 (1,4-Butanediphosphonic acid)

3D Structure for HMDB0244204 (1,4-Butanediphosphonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra