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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:54:59 UTC

Update Date

2022-03-07 02:55:50 UTC

HMDB ID

HMDB0038592

Secondary Accession Numbers

HMDB38592

Metabolite Identification

Common Name

Brassicanal B

Description

Brassicanal B 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. Brassicanal B has been detected, but not quantified in, brassicas. This could make brassicanal b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Brassicanal B.

Structure

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


  Mrv0541 05061310322D          

 16 18  0  0  0  0            999 V2000
    2.9708    3.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4962    1.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    2.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4356    0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    2.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288    1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4519    0.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942    1.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068    2.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    2.1885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132   -0.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669    3.3103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    1.4253    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
  8  4  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038592

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(O)CSC2=C(C=O)C3=CC=CC=C3N12

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO2S/c1-12(15)7-16-11-9(6-14)8-4-2-3-5-10(8)13(11)12/h2-6,15H,7H2,1H3

> <INCHI_KEY>
ZIEFIDANMCIAOW-UHFFFAOYSA-N

> <FORMULA>
C12H11NO2S

> <MOLECULAR_WEIGHT>
233.286

> <EXACT_MASS>
233.051049291

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.967352391407335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3-methyl-2H,3H-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.9496213166666663

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.675156430196289

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8156865774321433

> <JCHEM_POLAR_SURFACE_AREA>
42.230000000000004

> <JCHEM_REFRACTIVITY>
65.0337

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-methyl-2H-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

> <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       5.545   6.139   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.260   3.355   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.813   4.829   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.207   2.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.313   5.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   0.161   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.229   4.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.707   2.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.444   1.701   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.260   4.055   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.216   2.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.493   5.015   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.720   4.085   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       5.065  -0.583   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.485   6.179   0.000  0.00  0.00           O+0
HETATM   16  S   UNK     0       3.676   2.661   0.000  0.00  0.00           S+0
CONECT    1   12                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    9   14                                                       
CONECT    7   12   16                                                       
CONECT    8    4    9   10                                                  
CONECT    9    6    8   11                                                  
CONECT   10    5    8   13                                                  
CONECT   11    9   13   16                                                  
CONECT   12    1    7   13   15                                             
CONECT   13   10   11   12                                                  
CONECT   14    6                                                            
CONECT   15   12                                                            
CONECT   16    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0038592
HETATM    1  C1  UNL     1      -2.625  -0.696   0.887  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.955  -0.238  -0.391  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.029  -1.220  -1.379  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.758   0.937  -0.898  1.00  0.00           C  
HETATM    5  S1  UNL     1      -1.982   2.201   0.221  1.00  0.00           S  
HETATM    6  C4  UNL     1      -0.390   1.412   0.208  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.940   1.625   0.411  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.641   2.840   0.819  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.798   3.023   2.049  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.620   0.443   0.163  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.942   0.098   0.211  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.374  -1.186  -0.094  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.405  -2.098  -0.448  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.069  -1.742  -0.494  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.643  -0.467  -0.191  1.00  0.00           C  
HETATM   16  N1  UNL     1      -0.592   0.143  -0.159  1.00  0.00           N  
HETATM   17  H1  UNL     1      -2.687  -1.802   0.863  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.001  -0.420   1.758  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.633  -0.253   1.019  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.604  -1.962  -1.074  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.807   0.801  -0.639  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.546   1.168  -1.940  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.018   3.567   0.119  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.684   0.825   0.489  1.00  0.00           H  
HETATM   25  H9  UNL     1       4.430  -1.404  -0.041  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.708  -3.107  -0.691  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.336  -2.490  -0.777  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   16
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6
CONECT    6    7    7   16
CONECT    7    8   10
CONECT    8    9    9   23
CONECT   10   11   11   15
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   16
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-dihydro-3-Hydroxy-3-methylthiazolo[3,2-a]indole-9-carboxaldehyde, 9ci	HMDB

Chemical Formula

C₁₂H₁₁NO₂S

Average Molecular Weight

233.286

Monoisotopic Molecular Weight

233.051049291

IUPAC Name

3-hydroxy-3-methyl-2H,3H-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

Traditional Name

3-hydroxy-3-methyl-2H-[1,3]thiazolo[3,2-a]indole-9-carbaldehyde

CAS Registry Number

126654-63-5

SMILES

CC1(O)CSC2=C(C=O)C3=CC=CC=C3N12

InChI Identifier

InChI=1S/C12H11NO2S/c1-12(15)7-16-11-9(6-14)8-4-2-3-5-10(8)13(11)12/h2-6,15H,7H2,1H3

InChI Key

ZIEFIDANMCIAOW-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
Aryl thioether
Alkylarylthioether
Aryl-aldehyde
Substituted pyrrole
Vinylogous thioester
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous amide
Alkanolamine
Thioether
Azacycle
Aldehyde
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen 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: HMDB0038592)
Cytoplasm (HMDB: HMDB0038592)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038592)

Source

Exogenous

Food

Food (HMDB: HMDB0038592)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0038592)

Not Available

Nutrient (HMDB: HMDB0038592)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	169 - 170 °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	0.75 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.95	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.68	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.03 m³·mol⁻¹	ChemAxon
Polarizability	23.97 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]+	148.935	31661259
DarkChem	[M-H]-	146.397	31661259
DeepCCS	[M-2H]-	180.914	30932474
DeepCCS	[M+Na]+	155.887	30932474
AllCCS	[M+H]+	149.5	32859911
AllCCS	[M+H-H2O]+	145.6	32859911
AllCCS	[M+NH4]+	153.2	32859911
AllCCS	[M+Na]+	154.2	32859911
AllCCS	[M-H]-	151.9	32859911
AllCCS	[M+Na-2H]-	151.6	32859911
AllCCS	[M+HCOO]-	151.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brassicanal B	CC1(O)CSC2=C(C=O)C3=CC=CC=C3N12	3145.5	Standard polar	33892256
Brassicanal B	CC1(O)CSC2=C(C=O)C3=CC=CC=C3N12	2088.6	Standard non polar	33892256
Brassicanal B	CC1(O)CSC2=C(C=O)C3=CC=CC=C3N12	2353.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Brassicanal B,1TMS,isomer #1	CC1(O[Si](C)(C)C)CSC2=C(C=O)C3=CC=CC=C3N21	2262.8	Semi standard non polar	33892256
Brassicanal B,1TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)CSC2=C(C=O)C3=CC=CC=C3N21	2492.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Brassicanal B GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2950000000-9f81df31a76c7bb323d3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brassicanal B GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-9750000000-b70eede8e0d948f0f227	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brassicanal B 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 - Brassicanal B 10V, Positive-QTOF	splash10-001i-0090000000-8dedddb75a91d9331d18	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 20V, Positive-QTOF	splash10-00lr-0190000000-90d7df8323eca5fe4f95	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 40V, Positive-QTOF	splash10-0006-0920000000-1a0ed37799920b69e00a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 10V, Negative-QTOF	splash10-001i-0090000000-81782216380b97443844	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 20V, Negative-QTOF	splash10-0006-0940000000-b0a27b9a70de6f905b0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 40V, Negative-QTOF	splash10-0079-9000000000-c9f3e90eef4a220cabe0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 10V, Negative-QTOF	splash10-0f89-0190000000-5326774316e9f99d86a2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 20V, Negative-QTOF	splash10-0f8i-0590000000-b63771dcd2ef2cea6b28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 40V, Negative-QTOF	splash10-00di-0910000000-9c052611b1c98ac71d44	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 10V, Positive-QTOF	splash10-001i-0090000000-e542e9ee9b89db54a6dc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 20V, Positive-QTOF	splash10-001i-0190000000-fa2a31c34719e9e55215	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal B 40V, Positive-QTOF	splash10-0036-2920000000-718b504ddf61a262ad25	2021-09-24	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

FDB017982

KNApSAcK ID

C00036837

Chemspider ID

326803

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

368117

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 Brassicanal B (HMDB0038592)

MOL for HMDB0038592 (Brassicanal B)

3D MOL for HMDB0038592 (Brassicanal B)

3D SDF for HMDB0038592 (Brassicanal B)

3D-SDF for HMDB0038592 (Brassicanal B)

PDB for HMDB0038592 (Brassicanal B)

3D PDB for HMDB0038592 (Brassicanal B)

SMILES for HMDB0038592 (Brassicanal B)

INCHI for HMDB0038592 (Brassicanal B)

Structure for HMDB0038592 (Brassicanal B)

3D Structure for HMDB0038592 (Brassicanal B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra