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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:54:57 UTC

Update Date

2023-02-21 17:26:38 UTC

HMDB ID

HMDB0038591

Secondary Accession Numbers

HMDB38591

Metabolite Identification

Common Name

Brassicanal A

Description

Brassicanal A 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 A has been detected, but not quantified in, several different foods, such as brassicas, cauliflowers (Brassica oleracea var. botrytis), chinese cabbages (Brassica rapa), and radishes (Raphanus sativus). This could make brassicanal a a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Brassicanal A.

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       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0      -0.320   2.843   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   11                                                       
CONECT    6    3    7    8                                                  
CONECT    7    5    6    9                                                  
CONECT    8    4    6   10                                                  
CONECT    9    7   10   12                                                  
CONECT   10    8    9                                                       
CONECT   11    5                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Formyl-2-(methylthio)indole	HMDB
2-Sulphanyl-1H-indole-3-carbaldehyde	Generator

Chemical Formula

C₉H₇NOS

Average Molecular Weight

177.223

Monoisotopic Molecular Weight

177.024834541

IUPAC Name

2-sulfanyl-1H-indole-3-carbaldehyde

Traditional Name

2-sulfanyl-1H-indole-3-carbaldehyde

CAS Registry Number

113866-44-7

SMILES

SC1=C(C=O)C2=CC=CC=C2N1

InChI Identifier

InChI=1S/C9H7NOS/c11-5-7-6-3-1-2-4-8(6)10-9(7)12/h1-5,10,12H

InChI Key

ITVZJCAUYSGPDZ-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-aldehyde
Substituted pyrrole
Benzenoid
Pyrrole
Vinylogous amide
Heteroaromatic compound
Arylthiol
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aldehyde
Organosulfur compound
Organooxygen compound
Organonitrogen 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

Membrane (HMDB: HMDB0038591)
Cell membrane (HMDB: HMDB0038591)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038591)

Source

Exogenous

Exogenous (HMDB: HMDB0038591)

Food

Food (HMDB: HMDB0038591)

Vegetable

Cabbage

Chinese cabbage (FooDB: FOOD00035)
Cauliflower (FooDB: FOOD00031)

Root vegetable

Radish (FooDB: FOOD00153)

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0038591)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038591)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 213 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	186.4 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	0.1 g/L	ALOGPS
logP	2.56	ALOGPS
logP	1.97	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.28	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.86 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.99 m³·mol⁻¹	ChemAxon
Polarizability	18.15 Å³	ChemAxon
Number of Rings	2	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]+	135.999	31661259
DarkChem	[M-H]-	134.094	31661259
DeepCCS	[M+H]+	129.05	30932474
DeepCCS	[M-H]-	125.221	30932474
DeepCCS	[M-2H]-	162.249	30932474
DeepCCS	[M+Na]+	137.788	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.4	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	133.3	32859911
AllCCS	[M+Na-2H]-	133.9	32859911
AllCCS	[M+HCOO]-	134.6	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.	5.14 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3007 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1769.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	433.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	133.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	280.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	435.9 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	470.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	170.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	932.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	390.6 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	1262.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	341.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	494.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	391.5 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	155.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brassicanal A	SC1=C(C=O)C2=CC=CC=C2N1	2898.6	Standard polar	33892256
Brassicanal A	SC1=C(C=O)C2=CC=CC=C2N1	2078.6	Standard non polar	33892256
Brassicanal A	SC1=C(C=O)C2=CC=CC=C2N1	2106.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Brassicanal A,1TMS,isomer #1	C[Si](C)(C)SC1=C(C=O)C2=CC=CC=C2[NH]1	1968.1	Semi standard non polar	33892256
Brassicanal A,1TMS,isomer #1	C[Si](C)(C)SC1=C(C=O)C2=CC=CC=C2[NH]1	1758.1	Standard non polar	33892256
Brassicanal A,1TMS,isomer #2	C[Si](C)(C)N1C(S)=C(C=O)C2=CC=CC=C21	2080.5	Semi standard non polar	33892256
Brassicanal A,1TMS,isomer #2	C[Si](C)(C)N1C(S)=C(C=O)C2=CC=CC=C21	1837.9	Standard non polar	33892256
Brassicanal A,2TMS,isomer #1	C[Si](C)(C)SC1=C(C=O)C2=CC=CC=C2N1[Si](C)(C)C	2129.4	Semi standard non polar	33892256
Brassicanal A,2TMS,isomer #1	C[Si](C)(C)SC1=C(C=O)C2=CC=CC=C2N1[Si](C)(C)C	1899.2	Standard non polar	33892256
Brassicanal A,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC1=C(C=O)C2=CC=CC=C2[NH]1	2188.1	Semi standard non polar	33892256
Brassicanal A,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC1=C(C=O)C2=CC=CC=C2[NH]1	1975.4	Standard non polar	33892256
Brassicanal A,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(S)=C(C=O)C2=CC=CC=C21	2274.0	Semi standard non polar	33892256
Brassicanal A,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(S)=C(C=O)C2=CC=CC=C21	2029.9	Standard non polar	33892256
Brassicanal A,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC1=C(C=O)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	2499.5	Semi standard non polar	33892256
Brassicanal A,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC1=C(C=O)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	2317.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Brassicanal A GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-0900000000-4b2f2fe3cdbabdbcab83	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brassicanal A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brassicanal A 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 A 10V, Positive-QTOF	splash10-004i-0900000000-daba7a018f382401701d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 20V, Positive-QTOF	splash10-002f-0900000000-820baa7bd286ad3d13e2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 40V, Positive-QTOF	splash10-03xu-1900000000-97c7b0d4204ace36ee90	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 10V, Negative-QTOF	splash10-0006-0900000000-201029507402e4e3d129	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 20V, Negative-QTOF	splash10-002f-0900000000-18b4f42bf554ec404177	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 40V, Negative-QTOF	splash10-001l-6900000000-3e7538df093f39a205fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 10V, Positive-QTOF	splash10-004i-0900000000-d4ae4379cb5d380d8382	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 20V, Positive-QTOF	splash10-01r6-0900000000-8a523b088d6e333f9ccb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 40V, Positive-QTOF	splash10-0gbc-5900000000-861cbaeed5f9020e1d89	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 10V, Negative-QTOF	splash10-004i-0900000000-779437f8212ab6e221b7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 20V, Negative-QTOF	splash10-0002-0900000000-766441f9a0e31667c89c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassicanal A 40V, Negative-QTOF	splash10-00di-2900000000-dfe1a4d0678e220480cc	2021-09-25	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

Membrane

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10910114

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1869671

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 A (HMDB0038591)

MOL for HMDB0038591 (Brassicanal A)

3D MOL for HMDB0038591 (Brassicanal A)

3D SDF for HMDB0038591 (Brassicanal A)

3D-SDF for HMDB0038591 (Brassicanal A)

PDB for HMDB0038591 (Brassicanal A)

3D PDB for HMDB0038591 (Brassicanal A)

SMILES for HMDB0038591 (Brassicanal A)

INCHI for HMDB0038591 (Brassicanal A)

Structure for HMDB0038591 (Brassicanal A)

3D Structure for HMDB0038591 (Brassicanal A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra