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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:26:10 UTC

Update Date

2021-09-26 22:57:07 UTC

HMDB ID

HMDB0247429

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Chlorotheophylline

Description

8-Chlorotheophylline, also known as S8CT, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Based on a literature review a significant number of articles have been published on 8-Chlorotheophylline. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-chlorotheophylline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Chlorotheophylline 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


  Mrv0541 05041404592D          

 14 15  0  0  0  0            999 V2000
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  5  2  0  0  0  0
 14  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247429

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(N=C(Cl)N2)C(=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)

> <INCHI_KEY>
RYIGNEOBDRVTHA-UHFFFAOYSA-N

> <FORMULA>
C7H7ClN4O2

> <MOLECULAR_WEIGHT>
214.609

> <EXACT_MASS>
214.025753195

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.354059188616656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-chloro-1,3-dimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.10537535166666644

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.689091313343596

> <JCHEM_PKA_STRONGEST_BASIC>
-0.14046295622032068

> <JCHEM_POLAR_SURFACE_AREA>
69.30000000000001

> <JCHEM_REFRACTIVITY>
48.6507

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-chlorotheophylline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    4    5    9                                                  
CONECT    4    3   10   11                                                  
CONECT    5    3   12   13                                                  
CONECT    6    8    9   10                                                  
CONECT    7   11   12   14                                                  
CONECT    8    6                                                            
CONECT    9    3    6                                                       
CONECT   10    4    6                                                       
CONECT   11    1    4    7                                                  
CONECT   12    2    5    7                                                  
CONECT   13    5                                                            
CONECT   14    7                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,3-Dimethyl-8-chloroxanthine	ChEBI
8-Chloro-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione	ChEBI
Sodium-8-chlorotheophylline	HMDB
S8CT	HMDB
8-Chlorotheophylline, sodium salt	HMDB

Chemical Formula

C₇H₇ClN₄O₂

Average Molecular Weight

214.609

Monoisotopic Molecular Weight

214.025753195

IUPAC Name

8-chloro-1,3-dimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Traditional Name

8-chlorotheophylline

CAS Registry Number

Not Available

SMILES

CN1C2=C(N=C(Cl)N2)C(=O)N(C)C1=O

InChI Identifier

InChI=1S/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)

InChI Key

RYIGNEOBDRVTHA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
Aryl chloride
Aryl halide
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:59771 )
purines (CHEBI:59771 )

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	0.44	ALOGPS
logP	0.11	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-0.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.65 m³·mol⁻¹	ChemAxon
Polarizability	19.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	139.294	30932474
DeepCCS	[M-H]-	136.899	30932474
DeepCCS	[M-2H]-	171.629	30932474
DeepCCS	[M+Na]+	146.088	30932474
AllCCS	[M+H]+	143.3	32859911
AllCCS	[M+H-H2O]+	139.2	32859911
AllCCS	[M+NH4]+	147.0	32859911
AllCCS	[M+Na]+	148.1	32859911
AllCCS	[M-H]-	141.1	32859911
AllCCS	[M+Na-2H]-	141.5	32859911
AllCCS	[M+HCOO]-	142.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Chlorotheophylline	CN1C2=C(N=C(Cl)N2)C(=O)N(C)C1=O	2406.8	Standard polar	33892256
8-Chlorotheophylline	CN1C2=C(N=C(Cl)N2)C(=O)N(C)C1=O	2093.0	Standard non polar	33892256
8-Chlorotheophylline	CN1C2=C(N=C(Cl)N2)C(=O)N(C)C1=O	2086.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Chlorotheophylline,1TMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C)C(Cl)=N2)N(C)C1=O	2006.9	Semi standard non polar	33892256
8-Chlorotheophylline,1TMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C)C(Cl)=N2)N(C)C1=O	2099.1	Standard non polar	33892256
8-Chlorotheophylline,1TMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C)C(Cl)=N2)N(C)C1=O	2704.6	Standard polar	33892256
8-Chlorotheophylline,1TBDMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(Cl)=N2)N(C)C1=O	2240.0	Semi standard non polar	33892256
8-Chlorotheophylline,1TBDMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(Cl)=N2)N(C)C1=O	2313.0	Standard non polar	33892256
8-Chlorotheophylline,1TBDMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(Cl)=N2)N(C)C1=O	2713.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chlorotheophylline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-1900000000-e2b83fe635d076ddc4f2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chlorotheophylline 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 - 8-Chlorotheophylline 10V, Positive-QTOF	splash10-014i-0090000000-a0344a03e9a280090899	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 20V, Positive-QTOF	splash10-066r-0960000000-90b0457a4008057e096e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 40V, Positive-QTOF	splash10-0059-9800000000-cf2ce33acb02466b8bdb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 10V, Negative-QTOF	splash10-03di-0090000000-19e588057b5718f99e9c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 20V, Negative-QTOF	splash10-03di-0590000000-03b5cffda9b2c3baf818	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 40V, Negative-QTOF	splash10-0pdi-9600000000-9d00883a617ae9abfe9f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 10V, Positive-QTOF	splash10-014i-0090000000-676adaf946c311e7a025	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 20V, Positive-QTOF	splash10-014i-0390000000-f076353f198f7b9c2116	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 40V, Positive-QTOF	splash10-0ue9-0900000000-4e32070d3404c4b76718	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 10V, Negative-QTOF	splash10-03di-0090000000-ffc0ade7b782ecb20de1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 20V, Negative-QTOF	splash10-03di-4290000000-f36e973f4b30040315d9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chlorotheophylline 40V, Negative-QTOF	splash10-001i-9200000000-77490b7a37f11ea6ba50	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	¹³C NMR Spectrum (1D, 300 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	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	¹H NMR Spectrum (1D, 500 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, 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	¹H NMR Spectrum (1D, 700 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	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10211

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

8-Chlorotheophylline

METLIN ID

Not Available

PubChem Compound

10661

PDB ID

Not Available

ChEBI ID

59771

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1838361

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 8-Chlorotheophylline (HMDB0247429)

MOL for HMDB0247429 (8-Chlorotheophylline)

3D MOL for HMDB0247429 (8-Chlorotheophylline)

3D SDF for HMDB0247429 (8-Chlorotheophylline)

3D-SDF for HMDB0247429 (8-Chlorotheophylline)

PDB for HMDB0247429 (8-Chlorotheophylline)

3D PDB for HMDB0247429 (8-Chlorotheophylline)

SMILES for HMDB0247429 (8-Chlorotheophylline)

INCHI for HMDB0247429 (8-Chlorotheophylline)

Structure for HMDB0247429 (8-Chlorotheophylline)

3D Structure for HMDB0247429 (8-Chlorotheophylline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra