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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:53:42 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038570

Secondary Accession Numbers

HMDB38570

Metabolite Identification

Common Name

Cyclobrassinin sulfoxide

Description

Cyclobrassinin sulfoxide belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Cyclobrassinin sulfoxide has been detected, but not quantified in, brassicas. This could make cyclobrassinin sulfoxide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyclobrassinin sulfoxide.

Structure

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


  Mrv0541 05061310322D          

 16 18  0  0  0  0            999 V2000
   -1.1544    1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    0.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7556    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 12  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  1  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038570

> <DATABASE_NAME>
hmdb

> <SMILES>
CS(=O)C1=NCC2=C(NC3=CC=CC=C23)S1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10N2OS2/c1-16(14)11-12-6-8-7-4-2-3-5-9(7)13-10(8)15-11/h2-5,13H,6H2,1H3

> <INCHI_KEY>
YUXKTUVIOWXKPA-UHFFFAOYSA-N

> <FORMULA>
C11H10N2OS2

> <MOLECULAR_WEIGHT>
250.34

> <EXACT_MASS>
250.023454332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.942574175989137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methanesulfinyl-4H,9H-[1,3]thiazino[6,5-b]indole

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
1.7410562233333333

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.102228333224582

> <JCHEM_PKA_STRONGEST_BASIC>
1.3009752709578304

> <JCHEM_POLAR_SURFACE_AREA>
45.22

> <JCHEM_REFRACTIVITY>
69.0039

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methanesulfinyl-4H,9H-[1,3]thiazino[6,5-b]indole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.155   2.875   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.173   1.090   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.303  -0.374   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -2.709   0.266   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0       0.858   2.235   0.000  0.00  0.00           S+0
HETATM   16  S   UNK     0      -1.679   1.410   0.000  0.00  0.00           S+0
CONECT    1   16                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    9                                                       
CONECT    6    8   12                                                       
CONECT    7    4    8    9                                                  
CONECT    8    6    7   10                                                  
CONECT    9    5    7   13                                                  
CONECT   10    8   13   15                                                  
CONECT   11   12   15   16                                                  
CONECT   12    6   11                                                       
CONECT   13    9   10                                                       
CONECT   14   16                                                            
CONECT   15   10   11                                                       
CONECT   16    1   11   14                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0038570
HETATM    1  C1  UNL     1       4.657   1.343   0.355  1.00  0.00           C  
HETATM    2  S1  UNL     1       4.247  -0.403   0.262  1.00  0.00           S  
HETATM    3  O1  UNL     1       5.208  -1.154  -0.623  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.596  -0.711  -0.199  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.848  -1.482   0.467  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.496  -1.803   0.183  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.355  -0.721  -0.296  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.111   0.235  -1.164  1.00  0.00           C  
HETATM    9  N2  UNL     1      -0.861   1.077  -1.435  1.00  0.00           N  
HETATM   10  C6  UNL     1      -1.988   0.741  -0.786  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.259   1.278  -0.726  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.245   0.703   0.048  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.942  -0.442   0.780  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.685  -0.960   0.711  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.670  -0.407  -0.057  1.00  0.00           C  
HETATM   16  S2  UNL     1       1.856   0.053  -1.635  1.00  0.00           S  
HETATM   17  H1  UNL     1       5.718   1.471   0.057  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.378   1.813   1.297  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.065   1.833  -0.473  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.447  -2.671  -0.522  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.071  -2.212   1.138  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.770   1.905  -2.075  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.525   2.164  -1.283  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.249   1.117   0.105  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.699  -0.918   1.398  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.449  -1.848   1.279  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5    5   16
CONECT    5    6
CONECT    6    7   20   21
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   22
CONECT   10   11   11   15
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   14   25
CONECT   14   15   15   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cyclobrassinin sulphoxide	Generator
4,9-dihydro-2-(Methylsulfinyl)-1,3-thiazino[6,5-b]indole, 9ci	HMDB
2-Methanesulphinyl-4H,9H-[1,3]thiazino[6,5-b]indole	Generator

Chemical Formula

C₁₁H₁₀N₂OS₂

Average Molecular Weight

250.34

Monoisotopic Molecular Weight

250.023454332

IUPAC Name

2-methanesulfinyl-4H,9H-[1,3]thiazino[6,5-b]indole

Traditional Name

2-methanesulfinyl-4H,9H-[1,3]thiazino[6,5-b]indole

CAS Registry Number

128722-96-3

SMILES

CS(=O)C1=NCC2=C(NC3=CC=CC=C23)S1

InChI Identifier

InChI=1S/C11H10N2OS2/c1-16(14)11-12-6-8-7-4-2-3-5-9(7)13-10(8)15-11/h2-5,13H,6H2,1H3

InChI Key

YUXKTUVIOWXKPA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Aryl thioether
Benzenoid
Pyrrole
Heteroaromatic compound
Sulfoxide
Sulfinyl compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organosulfur compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038570)
Cytoplasm (HMDB: HMDB0038570)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038570)

Source

Exogenous

Food

Food (HMDB: HMDB0038570)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0038570)

Not Available

Nutrient (HMDB: HMDB0038570)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	188 - 190 °C	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
Water Solubility	1.75 g/L	ALOGPS
logP	1.77	ALOGPS
logP	1.74	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69 m³·mol⁻¹	ChemAxon
Polarizability	25.94 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
DarkChem	[M+H]+	155.253	31661259
DarkChem	[M-H]-	153.187	31661259
DeepCCS	[M-2H]-	183.999	30932474
DeepCCS	[M+Na]+	158.859	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	149.0	32859911
AllCCS	[M+NH4]+	156.4	32859911
AllCCS	[M+Na]+	157.4	32859911
AllCCS	[M-H]-	153.6	32859911
AllCCS	[M+Na-2H]-	153.4	32859911
AllCCS	[M+HCOO]-	153.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclobrassinin sulfoxide	CS(=O)C1=NCC2=C(NC3=CC=CC=C23)S1	3440.8	Standard polar	33892256
Cyclobrassinin sulfoxide	CS(=O)C1=NCC2=C(NC3=CC=CC=C23)S1	2532.7	Standard non polar	33892256
Cyclobrassinin sulfoxide	CS(=O)C1=NCC2=C(NC3=CC=CC=C23)S1	2554.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclobrassinin sulfoxide,1TMS,isomer #1	CS(=O)C1=NCC2=C(S1)N([Si](C)(C)C)C1=CC=CC=C21	2433.6	Semi standard non polar	33892256
Cyclobrassinin sulfoxide,1TMS,isomer #1	CS(=O)C1=NCC2=C(S1)N([Si](C)(C)C)C1=CC=CC=C21	2387.3	Standard non polar	33892256
Cyclobrassinin sulfoxide,1TBDMS,isomer #1	CS(=O)C1=NCC2=C(S1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2609.1	Semi standard non polar	33892256
Cyclobrassinin sulfoxide,1TBDMS,isomer #1	CS(=O)C1=NCC2=C(S1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2668.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclobrassinin sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p9-4930000000-11c4cd2a39faa51ea905	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclobrassinin sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclobrassinin sulfoxide 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 - Cyclobrassinin sulfoxide 10V, Positive-QTOF	splash10-0udi-0190000000-db5938179d4b91019884	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 20V, Positive-QTOF	splash10-0udi-2490000000-f9bbb4136e56172d6365	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 40V, Positive-QTOF	splash10-06r6-1920000000-1094659abfbb035faacd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 10V, Negative-QTOF	splash10-00di-2290000000-7ed3f2e72a4c79346145	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 20V, Negative-QTOF	splash10-000i-9200000000-29c52dea4c066eb6d153	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 40V, Negative-QTOF	splash10-052r-4900000000-3b8fa252cbf51ad54ee1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 10V, Negative-QTOF	splash10-0002-0090000000-dcd408d8704a3e2b8066	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 20V, Negative-QTOF	splash10-0002-2190000000-40f2c13f6666b88b8777	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 40V, Negative-QTOF	splash10-03di-2900000000-aa326735ef78a0b792f5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 10V, Positive-QTOF	splash10-0udi-0090000000-1043d01fd652b4399f71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 20V, Positive-QTOF	splash10-0udi-0090000000-1043d01fd652b4399f71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobrassinin sulfoxide 40V, Positive-QTOF	splash10-0udi-1930000000-e4939e2098d39c6a1d2d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB017960

KNApSAcK ID

C00055331

Chemspider ID

35014607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14585498

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cyclobrassinin sulfoxide (HMDB0038570)

MOL for HMDB0038570 (Cyclobrassinin sulfoxide)

3D MOL for HMDB0038570 (Cyclobrassinin sulfoxide)

3D SDF for HMDB0038570 (Cyclobrassinin sulfoxide)

3D-SDF for HMDB0038570 (Cyclobrassinin sulfoxide)

PDB for HMDB0038570 (Cyclobrassinin sulfoxide)

3D PDB for HMDB0038570 (Cyclobrassinin sulfoxide)

SMILES for HMDB0038570 (Cyclobrassinin sulfoxide)

INCHI for HMDB0038570 (Cyclobrassinin sulfoxide)

Structure for HMDB0038570 (Cyclobrassinin sulfoxide)

3D Structure for HMDB0038570 (Cyclobrassinin sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra