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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:37:33 UTC

Update Date

2021-09-26 23:07:12 UTC

HMDB ID

HMDB0253770

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one

Description

3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one, also known as KB-NB142-70, belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system. Based on a literature review very few articles have been published on 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,4-dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2h)-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one 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

  Mrv1652309112114372D          

 16 18  0  0  0  0            999 V2000
    4.1531    2.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5932    2.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704    2.1558    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    2.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457    3.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131    3.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3730    4.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0284    3.5174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8701    4.0988    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111    3.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4793    2.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378    2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    2.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402    3.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    3.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4134    1.7353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  1  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253770

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(SC3=C2SCCNC3=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO2S2/c13-6-1-2-8-7(5-6)9-10(16-8)11(14)12-3-4-15-9/h1-2,5,13H,3-4H2,(H,12,14)

> <INCHI_KEY>
DHUAGGSHTKPOHU-UHFFFAOYSA-N

> <FORMULA>
C11H9NO2S2

> <MOLECULAR_WEIGHT>
251.32

> <EXACT_MASS>
251.007470882

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
25.10249185171164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-8,14-dithia-11-azatricyclo[7.5.0.0^{2,7}]tetradeca-1(9),2(7),3,5-tetraen-10-one

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
1.9494678413333335

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.283922605180145

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.516734976836128

> <JCHEM_PKA_STRONGEST_BASIC>
-2.551573310226322

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
66.1313

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-8,14-dithia-11-azatricyclo[7.5.0.0^{2,7}]tetradeca-1(9),2(7),3,5-tetraen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       7.752   5.043   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.707   3.912   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       5.171   4.024   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0       4.301   5.295   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.752   6.767   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.184   7.333   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.296   8.869   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       7.520   6.566   0.000  0.00  0.00           N+0
HETATM    9  S   UNK     0       3.491   7.651   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0       2.261   6.725   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.761   5.269   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.751   4.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.239   4.401   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.262   5.857   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.749   7.019   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.772   3.239   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    1                                                       
CONECT    9    5   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0253770
HETATM    1  O1  UNL     1      -2.181   2.927   1.007  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.131   1.680   0.747  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.333   0.948   0.622  1.00  0.00           N  
HETATM    4  C2  UNL     1      -3.413  -0.451   0.223  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.842  -0.686  -1.125  1.00  0.00           C  
HETATM    6  S1  UNL     1      -1.122  -0.767  -1.344  1.00  0.00           S  
HETATM    7  C4  UNL     1      -0.157   0.243  -0.158  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.731   1.211   0.620  1.00  0.00           C  
HETATM    9  S2  UNL     1       0.596   1.837   1.512  1.00  0.00           S  
HETATM   10  C6  UNL     1       1.830   0.859   0.877  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.213   0.769   1.110  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.992  -0.143   0.433  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.329  -0.940  -0.468  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.117  -1.873  -1.163  1.00  0.00           O  
HETATM   15  C10 UNL     1       1.986  -0.868  -0.710  1.00  0.00           C  
HETATM   16  C11 UNL     1       1.184   0.065  -0.018  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.187   1.464   0.834  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.993  -1.129   0.995  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.508  -0.691   0.177  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.296  -1.663  -1.483  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.329   0.062  -1.820  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.630   1.438   1.836  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.052  -0.245   0.581  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.698  -2.493  -1.842  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.596  -1.553  -1.443  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7
CONECT    7    8    8   16
CONECT    8    9
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14   15
CONECT   14   24
CONECT   15   16   16   25
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
KB-NB142-70	HMDB

Chemical Formula

C₁₁H₉NO₂S₂

Average Molecular Weight

251.32

Monoisotopic Molecular Weight

251.007470882

IUPAC Name

4-hydroxy-8,14-dithia-11-azatricyclo[7.5.0.0^{2,7}]tetradeca-1(9),2(7),3,5-tetraen-10-one

Traditional Name

4-hydroxy-8,14-dithia-11-azatricyclo[7.5.0.0^{2,7}]tetradeca-1(9),2(7),3,5-tetraen-10-one

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(SC3=C2SCCNC3=O)C=C1

InChI Identifier

InChI=1S/C11H9NO2S2/c13-6-1-2-8-7(5-6)9-10(16-8)11(14)12-3-4-15-9/h1-2,5,13H,3-4H2,(H,12,14)

InChI Key

DHUAGGSHTKPOHU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiophenes

Sub Class

1-benzothiophenes

Direct Parent

1-benzothiophenes

Alternative Parents

Substituents

1-benzothiophene
2-heteroaryl carboxamide
Aryl thioether
Phenol
Alkylarylthioether
1-hydroxy-2-unsubstituted benzenoid
Vinylogous thioester
Benzenoid
Heteroaromatic compound
Thiophene
Lactam
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Thioether
Azacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.14	ALOGPS
logP	1.95	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.13 m³·mol⁻¹	ChemAxon
Polarizability	25.1 Å³	ChemAxon
Number of Rings	3	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]+	149.556	30932474
DeepCCS	[M-H]-	147.198	30932474
DeepCCS	[M-2H]-	181.35	30932474
DeepCCS	[M+Na]+	155.985	30932474
AllCCS	[M+H]+	151.4	32859911
AllCCS	[M+H-H2O]+	147.5	32859911
AllCCS	[M+NH4]+	155.0	32859911
AllCCS	[M+Na]+	156.1	32859911
AllCCS	[M-H]-	153.1	32859911
AllCCS	[M+Na-2H]-	152.8	32859911
AllCCS	[M+HCOO]-	152.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one	OC1=CC2=C(SC3=C2SCCNC3=O)C=C1	4212.3	Standard polar	33892256
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one	OC1=CC2=C(SC3=C2SCCNC3=O)C=C1	2410.4	Standard non polar	33892256
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one	OC1=CC2=C(SC3=C2SCCNC3=O)C=C1	2865.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2SC3=C(SCCN([Si](C)(C)C)C3=O)C2=C1	2618.5	Semi standard non polar	33892256
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2SC3=C(SCCN([Si](C)(C)C)C3=O)C2=C1	2499.6	Standard non polar	33892256
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2SC3=C(SCCN([Si](C)(C)C)C3=O)C2=C1	2979.6	Standard polar	33892256
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2SC3=C(SCCN([Si](C)(C)C(C)(C)C)C3=O)C2=C1	3015.2	Semi standard non polar	33892256
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2SC3=C(SCCN([Si](C)(C)C(C)(C)C)C3=O)C2=C1	2945.6	Standard non polar	33892256
3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2SC3=C(SCCN([Si](C)(C)C(C)(C)C)C3=O)C2=C1	3188.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmi-0290000000-f61a0839b0b56d511f79	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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

24606070

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45258277

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 3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one (HMDB0253770)

MOL for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

3D MOL for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

3D SDF for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

3D-SDF for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

PDB for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

3D PDB for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

SMILES for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

INCHI for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

Structure for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

3D Structure for HMDB0253770 (3,4-Dihydro-9-hydroxy-[1]benzothieno[2,3-f]-1,4-thiazepin-5(2H)-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra