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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:09:57 UTC

Update Date

2023-02-21 17:27:02 UTC

HMDB ID

HMDB0039638

Secondary Accession Numbers

HMDB39638

Metabolite Identification

Common Name

Brassilexin

Description

Brassilexin belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Brassilexin has been detected, but not quantified in, several different foods, such as brassicas, cauliflowers (Brassica oleracea var. botrytis), chinese cabbages (Brassica rapa), chinese mustards (Brassica juncea), and herbs and spices. This could make brassilexin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Brassilexin.

Structure

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

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       7.655   3.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.102   5.301   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.155   3.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.049   6.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.335   3.641   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.102   4.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.563   4.571   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.549   6.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.058   6.026   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.071   4.522   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.286   6.955   0.000  0.00  0.00           N+0
HETATM   12  S   UNK     0       1.518   5.995   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7   10                                                       
CONECT    6    3    7    8                                                  
CONECT    7    5    6    9                                                  
CONECT    8    4    6   11                                                  
CONECT    9    7   11   12                                                  
CONECT   10    5   12                                                       
CONECT   11    8    9                                                       
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8H-isothiazolo(5,4-b)Indole	HMDB
Brassilexine	HMDB

Chemical Formula

C₉H₆N₂S

Average Molecular Weight

174.222

Monoisotopic Molecular Weight

174.025168892

IUPAC Name

8H-[1,2]thiazolo[5,4-b]indole

Traditional Name

8H-[1,2]thiazolo[5,4-b]indole

CAS Registry Number

119752-76-0

SMILES

N1C2=C(C=NS2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C9H6N2S/c1-2-4-8-6(3-1)7-5-10-12-9(7)11-8/h1-5,11H

InChI Key

NHMBEDDKDVIBQD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Benzenoid
Heteroaromatic compound
Thiazole
Pyrrole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039638)
Cytoplasm (HMDB: HMDB0039638)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039638)

Source

Exogenous

Exogenous (HMDB: HMDB0039638)

Food

Food (HMDB: HMDB0039638)

Vegetable

Cabbage

Brassica

Brassicas (FooDB: FOOD00857)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0039638)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039638)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	164 - 167 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8938 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.43	ALOGPS
logP	2.42	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.78	ChemAxon
pKa (Strongest Basic)	0.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.68 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.34 m³·mol⁻¹	ChemAxon
Polarizability	17.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.58	31661259
DarkChem	[M-H]-	133.061	31661259
DeepCCS	[M-2H]-	162.784	30932474
DeepCCS	[M+Na]+	138.241	30932474
AllCCS	[M+H]+	134.8	32859911
AllCCS	[M+H-H2O]+	130.2	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.3	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	134.5	32859911
AllCCS	[M+HCOO]-	134.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.76 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6099 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.89 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	69.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2198.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	551.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	215.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	388.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	550.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	554.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	262.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1178.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	418.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1311.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	476.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	609.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	498.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	160.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brassilexin	N1C2=C(C=NS2)C2=CC=CC=C12	2532.4	Standard polar	33892256
Brassilexin	N1C2=C(C=NS2)C2=CC=CC=C12	1728.5	Standard non polar	33892256
Brassilexin	N1C2=C(C=NS2)C2=CC=CC=C12	1914.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Brassilexin,1TMS,isomer #1	C[Si](C)(C)N1C2=CC=CC=C2C2=C1SN=C2	2006.3	Semi standard non polar	33892256
Brassilexin,1TMS,isomer #1	C[Si](C)(C)N1C2=CC=CC=C2C2=C1SN=C2	2013.8	Standard non polar	33892256
Brassilexin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=C1SN=C2	2191.8	Semi standard non polar	33892256
Brassilexin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=C1SN=C2	2191.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Brassilexin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-0900000000-5d553191ff9f899717f9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brassilexin 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 - Brassilexin 10V, Positive-QTOF	splash10-004i-0900000000-bf8b8ee0b9b01fc0c2ec	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 20V, Positive-QTOF	splash10-004i-0900000000-be894386f7ed39d42b4d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 40V, Positive-QTOF	splash10-004j-1900000000-1a7dcfc66dbfca6644c9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 10V, Negative-QTOF	splash10-00di-0900000000-797411d7ade8a948debd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 20V, Negative-QTOF	splash10-0002-0900000000-9ab2dd4c6e789b520d1b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 40V, Negative-QTOF	splash10-0002-0900000000-eafa615f6e5a764e75a9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 10V, Negative-QTOF	splash10-00di-0900000000-9bcf7e2f83bab5a3e2a8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 20V, Negative-QTOF	splash10-00di-0900000000-9bcf7e2f83bab5a3e2a8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 40V, Negative-QTOF	splash10-00di-0900000000-3544992f5b647a14b42b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 10V, Positive-QTOF	splash10-004i-0900000000-2ca41d8f7758834ebb8f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 20V, Positive-QTOF	splash10-004i-0900000000-2ca41d8f7758834ebb8f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassilexin 40V, Positive-QTOF	splash10-004i-0900000000-9c0501577d21d63675c8	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB019266

KNApSAcK ID

C00027108

Chemspider ID

19992709

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135413564

PDB ID

Not Available

ChEBI ID

169691

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1879001

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pedras MS, Jha M: Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: expanding the scope of the vilsmeier formylation. J Org Chem. 2005 Mar 4;70(5):1828-34. [PubMed:15730307 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Brassilexin (HMDB0039638)

MOL for HMDB0039638 (Brassilexin)

3D MOL for HMDB0039638 (Brassilexin)

3D SDF for HMDB0039638 (Brassilexin)

3D-SDF for HMDB0039638 (Brassilexin)

PDB for HMDB0039638 (Brassilexin)

3D PDB for HMDB0039638 (Brassilexin)

SMILES for HMDB0039638 (Brassilexin)

INCHI for HMDB0039638 (Brassilexin)

Structure for HMDB0039638 (Brassilexin)

3D Structure for HMDB0039638 (Brassilexin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra