Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:41:32 UTC

Update Date

2022-03-07 02:56:29 UTC

HMDB ID

HMDB0040147

Secondary Accession Numbers

HMDB40147

Metabolite Identification

Common Name

2-Bromo-1H-indole-3-carboxaldehyde

Description

2-Bromo-1H-indole-3-carboxaldehyde 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. Based on a literature review very few articles have been published on 2-Bromo-1H-indole-3-carboxaldehyde.

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 Br   UNK     0      -0.320   2.843   0.000  0.00  0.00          Br+0
HETATM   11  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7   12                                                       
CONECT    6    3    7    8                                                  
CONECT    7    5    6    9                                                  
CONECT    8    4    6   11                                                  
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    8    9                                                       
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-bromo-3-Formylindole	HMDB
Gbetagamma modulator I, m119	HMDB

Chemical Formula

C₉H₆BrNO

Average Molecular Weight

224.054

Monoisotopic Molecular Weight

222.963276466

IUPAC Name

2-bromo-1H-indole-3-carbaldehyde

Traditional Name

2-bromo-1H-indole-3-carbaldehyde

CAS Registry Number

119910-45-1

SMILES

BrC1=C(C=O)C2=CC=CC=C2N1

InChI Identifier

InChI=1S/C9H6BrNO/c10-9-7(5-12)6-3-1-2-4-8(6)11-9/h1-5,11H

InChI Key

WIRLVLFYTTULCM-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
Aryl bromide
Aryl halide
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous halide
Vinylogous amide
Azacycle
Hydrocarbon derivative
Organic oxide
Aldehyde
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040147)
Cell membrane (HMDB: HMDB0040147)

Source

Exogenous

Exogenous (HMDB: HMDB0040147)

Food

Food (HMDB: HMDB0040147)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040147)

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
Water Solubility	0.79 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.25	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.56	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.86 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	51.13 m³·mol⁻¹	ChemAxon
Polarizability	18.48 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
DeepCCS	[M+H]+	128.079	30932474
DeepCCS	[M-H]-	124.25	30932474
DeepCCS	[M-2H]-	161.381	30932474
DeepCCS	[M+Na]+	136.92	30932474
AllCCS	[M+H]+	144.7	32859911
AllCCS	[M+H-H2O]+	140.4	32859911
AllCCS	[M+NH4]+	148.7	32859911
AllCCS	[M+Na]+	149.8	32859911
AllCCS	[M-H]-	136.0	32859911
AllCCS	[M+Na-2H]-	136.7	32859911
AllCCS	[M+HCOO]-	137.6	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.	6.28 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3896 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.42 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1997.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	556.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	367.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	573.7 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	624.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	270.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1185.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	459.6 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	1290.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	432.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	452.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	539.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	475.5 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	139.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Bromo-1H-indole-3-carboxaldehyde	BrC1=C(C=O)C2=CC=CC=C2N1	2468.7	Standard polar	33892256
2-Bromo-1H-indole-3-carboxaldehyde	BrC1=C(C=O)C2=CC=CC=C2N1	1875.3	Standard non polar	33892256
2-Bromo-1H-indole-3-carboxaldehyde	BrC1=C(C=O)C2=CC=CC=C2N1	1846.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Bromo-1H-indole-3-carboxaldehyde,1TMS,isomer #1	C[Si](C)(C)N1C(Br)=C(C=O)C2=CC=CC=C21	2027.1	Semi standard non polar	33892256
2-Bromo-1H-indole-3-carboxaldehyde,1TMS,isomer #1	C[Si](C)(C)N1C(Br)=C(C=O)C2=CC=CC=C21	1766.9	Standard non polar	33892256
2-Bromo-1H-indole-3-carboxaldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(Br)=C(C=O)C2=CC=CC=C21	2240.9	Semi standard non polar	33892256
2-Bromo-1H-indole-3-carboxaldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(Br)=C(C=O)C2=CC=CC=C21	1957.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-1950000000-90a3adce4a12e54123e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 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 - 2-Bromo-1H-indole-3-carboxaldehyde 10V, Positive-QTOF	splash10-00di-0090000000-86625569b3549010aee1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 20V, Positive-QTOF	splash10-00di-0090000000-4f68ad985d875edeaba6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 40V, Positive-QTOF	splash10-052f-0940000000-e4ec13b7c7e3fc33b04a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 10V, Negative-QTOF	splash10-00di-0190000000-bdaf6a2a3504561c518e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 20V, Negative-QTOF	splash10-00di-0490000000-c68fe500fb17f04d4a2b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 40V, Negative-QTOF	splash10-006x-0940000000-3f2b737df3192fe4425d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 10V, Positive-QTOF	splash10-00di-0090000000-13d1bb2571a2632fc789	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 20V, Positive-QTOF	splash10-00di-0090000000-0c43ba0e4368d335576c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 40V, Positive-QTOF	splash10-0udi-1920000000-6850745a9a782f1410af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 10V, Negative-QTOF	splash10-00di-0090000000-b07a322ad781fe166a02	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 20V, Negative-QTOF	splash10-0006-0910000000-9beef2a679973f3004cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Bromo-1H-indole-3-carboxaldehyde 40V, Negative-QTOF	splash10-004i-9000000000-e70570f51d7e71d64854	2021-09-22	Wishart 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

FDB019844

KNApSAcK ID

Not Available

Chemspider ID

319761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

360191

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 2-Bromo-1H-indole-3-carboxaldehyde (HMDB0040147)

MOL for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

3D MOL for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

3D SDF for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

3D-SDF for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

PDB for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

3D PDB for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

SMILES for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

INCHI for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

Structure for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

3D Structure for HMDB0040147 (2-Bromo-1H-indole-3-carboxaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra