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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-07-16 17:10:23 UTC

Update Date

2022-03-07 03:18:16 UTC

HMDB ID

HMDB0240376

Secondary Accession Numbers

None

Metabolite Identification

Common Name

DIBOA sulfate

Description

DIBOA sulfate, also known as diboa sulphate, belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. Based on a literature review very few articles have been published on DIBOA sulfate.

Structure

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

  Mrv1652307161919102D          

 17 18  0  0  0  0            999 V2000
   -2.9909    0.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4198    0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4198    0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7054   -0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9908    0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -0.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619    0.0786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5618    0.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2764    1.3161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2764    2.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8473    1.3161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8474   -0.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -0.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448    0.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794    0.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327    0.0782    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  7  8  1  0  0  0  0
  6  7  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 14  1  0  0  0  0
  8 13  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0240376

> <DATABASE_NAME>
hmdb

> <SMILES>
ON1C(=O)[C@@H](OS(O)(=O)=O)OC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO7S/c10-7-8(16-17(12,13)14)15-6-4-2-1-3-5(6)9(7)11/h1-4,8,11H,(H,12,13,14)/t8-/m1/s1

> <INCHI_KEY>
GNPNIYVSUDXFAF-MRVPVSSYSA-N

> <FORMULA>
C8H7NO7S

> <MOLECULAR_WEIGHT>
261.2

> <EXACT_MASS>
260.994322743

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
21.73844565377745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
0.15806829699999997

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.896200753179541

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.3010870360212046

> <JCHEM_PKA_STRONGEST_BASIC>
-5.095571134476963

> <JCHEM_POLAR_SURFACE_AREA>
113.37

> <JCHEM_REFRACTIVITY>
51.999100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R)-4-hydroxy-3-oxo-2H-1,4-benzoxazin-2-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JUL-19         0                                  
HETATM    1  C   UNK     0      -5.583   1.687   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.917   2.457   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.250   1.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.250   0.147   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.917  -0.623   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.583   0.147   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.249  -0.623   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.916   0.147   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.915   1.687   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -4.249   2.457   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -4.249   3.997   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.582   2.457   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.582  -0.623   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.083  -0.623   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.017   1.476   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.522   1.476   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0      -0.248   0.146   0.000  0.00  0.00           S+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    8    6                                                       
CONECT    8    9    7   13                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    1   11                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13   17    8                                                       
CONECT   14   17                                                            
CONECT   15   17                                                            
CONECT   16   17                                                            
CONECT   17   15   16   13   14                                             
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
DIBOA sulfuric acid	Generator
DIBOA sulphate	Generator
DIBOA sulphuric acid	Generator
[(2R)-4-Hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]oxidanesulfonate	HMDB
[(2R)-4-Hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]oxidanesulphonate	HMDB
[(2R)-4-Hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]oxidanesulphonic acid	HMDB
(R)-2,4-Dihydroxy-1,4-benzoxazin-3-one sulfate	HMDB
(R)-DIBOA sulfate	HMDB
2,4-Dihydroxy-1,4-benzoxazin-3-one sulfate	HMDB
DIBOA sulfate	HMDB

Chemical Formula

C₈H₇NO₇S

Average Molecular Weight

261.2

Monoisotopic Molecular Weight

260.994322743

IUPAC Name

[(2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]oxidanesulfonic acid

Traditional Name

[(2R)-4-hydroxy-3-oxo-2H-1,4-benzoxazin-2-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

ON1C(=O)[C@@H](OS(O)(=O)=O)OC2=CC=CC=C12

InChI Identifier

InChI=1S/C8H7NO7S/c10-7-8(16-17(12,13)14)15-6-4-2-1-3-5(6)9(7)11/h1-4,8,11H,(H,12,13,14)/t8-/m1/s1

InChI Key

GNPNIYVSUDXFAF-MRVPVSSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Benzoxazinones

Direct Parent

Benzoxazinones

Alternative Parents

Substituents

Benzoxazinone
Benzomorpholine
Benzenoid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Oxazinane
Organic sulfuric acid or derivatives
Hydroxamic acid
Oxacycle
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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: 23650214)

Excreta

Biofluid or Excreta

Urine (PMID: 23650214)

Source

Exogenous

Exogenous (HMDB: HMDB0240376)

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	-0.89	ALOGPS
logP	0.16	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52 m³·mol⁻¹	ChemAxon
Polarizability	21.74 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-2H]-	181.586	30932474
DeepCCS	[M+Na]+	156.597	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
DIBOA sulfate	ON1C(=O)[C@@H](OS(O)(=O)=O)OC2=CC=CC=C12	4135.8	Standard polar	33892256
DIBOA sulfate	ON1C(=O)[C@@H](OS(O)(=O)=O)OC2=CC=CC=C12	1956.9	Standard non polar	33892256
DIBOA sulfate	ON1C(=O)[C@@H](OS(O)(=O)=O)OC2=CC=CC=C12	2208.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
DIBOA sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)O[C@H]1OC2=CC=CC=C2N(O)C1=O	2159.4	Semi standard non polar	33892256
DIBOA sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)O[C@H]1OC2=CC=CC=C2N(O)C1=O	2185.1	Standard non polar	33892256
DIBOA sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)O[C@H]1OC2=CC=CC=C2N(O)C1=O	3613.5	Standard polar	33892256
DIBOA sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1OC2=CC=CC=C2N(O)C1=O	2405.2	Semi standard non polar	33892256
DIBOA sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1OC2=CC=CC=C2N(O)C1=O	2465.7	Standard non polar	33892256
DIBOA sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1OC2=CC=CC=C2N(O)C1=O	3572.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - DIBOA sulfate 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 - DIBOA sulfate 10V, Negative-QTOF	splash10-0a4i-0090000000-0f3d39245836c8fc5be5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DIBOA sulfate 20V, Negative-QTOF	splash10-0a4i-2190000000-c7e6f5ee3617608f3880	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DIBOA sulfate 40V, Negative-QTOF	splash10-00kb-9520000000-bd2fbafb6cf266208516	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DIBOA sulfate 10V, Positive-QTOF	splash10-03di-0090000000-20ffccc4bb0f57adea80	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DIBOA sulfate 20V, Positive-QTOF	splash10-03e9-0930000000-17e1e4b78f7e0d0d1a10	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DIBOA sulfate 40V, Positive-QTOF	splash10-074i-3900000000-96f2a3ad139246e2213e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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	Adult (>18 years old)	Both	Normal	23650214	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23650214	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156960849

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

Adhikari KB, Laursen BB, Gregersen PL, Schnoor HJ, Witten M, Poulsen LK, Jensen BM, Fomsgaard IS: Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans. Mol Nutr Food Res. 2013 Oct;57(10):1847-58. doi: 10.1002/mnfr.201300107. Epub 2013 May 3. [PubMed:23650214 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Showing metabocard for DIBOA sulfate (HMDB0240376)

MOL for HMDB0240376 (DIBOA sulfate)

3D MOL for HMDB0240376 (DIBOA sulfate)

3D SDF for HMDB0240376 (DIBOA sulfate)

3D-SDF for HMDB0240376 (DIBOA sulfate)

PDB for HMDB0240376 (DIBOA sulfate)

3D PDB for HMDB0240376 (DIBOA sulfate)

SMILES for HMDB0240376 (DIBOA sulfate)

INCHI for HMDB0240376 (DIBOA sulfate)

Structure for HMDB0240376 (DIBOA sulfate)

3D Structure for HMDB0240376 (DIBOA sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra