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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-07-12 23:01:06 UTC
HMDB IDHMDB0001190
Secondary Accession Numbers
  • HMDB01190
Metabolite Identification
Common NameIndoleacetaldehyde
DescriptionIndoleacetaldehyde, also known as tryptaldehyde, 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. Indoleacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Indoleacetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, indoleacetaldehyde participates in a number of enzymatic reactions. In particular, indoleacetaldehyde can be biosynthesized from tryptamine; which is mediated by the enzyme kynurenine 3-monooxygenase. In addition, indoleacetaldehyde can be converted into indoleacetic acid; which is catalyzed by the enzyme aldehyde dehydrogenase, mitochondrial. In humans, indoleacetaldehyde is involved in tryptophan metabolism. Outside of the human body, indoleacetaldehyde has been detected, but not quantified in, several different foods, such as nuts, turmerics, Alaska blueberries, summer savouries, and black raspberries. This could make indoleacetaldehyde a potential biomarker for the consumption of these foods. Indoleacetaldehyde is also a substrate for amine oxidase and 4-trimethylaminobutyraldehyde dehydrogenase.
Structure
Data?1582752183
Synonyms
ValueSource
1H-Indole-3-acetaldehydeChEBI
2-(indol-3-yl)AcetaldehydeChEBI
Indole-3-acetaldehydeChEBI
1H-indol-3-YlacetaldehydeHMDB
2-(3-Indolyl)acetaldehydeHMDB
indol-3-YlacetaldehydeHMDB
TryptaldehydeHMDB
Chemical FormulaC10H9NO
Average Molecular Weight159.1846
Monoisotopic Molecular Weight159.068413915
IUPAC Name2-(1H-indol-3-yl)acetaldehyde
Traditional Nameindole-3-acetaldehyde
CAS Registry Number2591-98-2
SMILES
O=CCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2
InChI KeyWHOOUMGHGSPMGR-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Substituted pyrrole
  • Benzenoid
  • Alpha-hydrogen aldehyde
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available131.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00002128
[M+H]+Not Available132.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002128
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.01 g/LALOGPS
logP2.32ALOGPS
logP1.55ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)14.73ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.86 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.53 m³·mol⁻¹ChemAxon
Polarizability16.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.63131661259
DarkChem[M-H]-132.22331661259
AllCCS[M+H]+133.95632859911
AllCCS[M-H]-134.30932859911
DeepCCS[M+H]+134.21530932474
DeepCCS[M-H]-130.42730932474
DeepCCS[M-2H]-168.04830932474
DeepCCS[M+Na]+143.34830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IndoleacetaldehydeO=CCC1=CNC2=C1C=CC=C22796.9Standard polar33892256
IndoleacetaldehydeO=CCC1=CNC2=C1C=CC=C21740.3Standard non polar33892256
IndoleacetaldehydeO=CCC1=CNC2=C1C=CC=C21790.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indoleacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=C[NH]C2=CC=CC=C121955.2Semi standard non polar33892256
Indoleacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=C[NH]C2=CC=CC=C121817.3Standard non polar33892256
Indoleacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=C[NH]C2=CC=CC=C122331.9Standard polar33892256
Indoleacetaldehyde,1TMS,isomer #2C[Si](C)(C)N1C=C(CC=O)C2=CC=CC=C211802.2Semi standard non polar33892256
Indoleacetaldehyde,1TMS,isomer #2C[Si](C)(C)N1C=C(CC=O)C2=CC=CC=C211762.3Standard non polar33892256
Indoleacetaldehyde,1TMS,isomer #2C[Si](C)(C)N1C=C(CC=O)C2=CC=CC=C212112.0Standard polar33892256
Indoleacetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=CC=C122145.2Semi standard non polar33892256
Indoleacetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=CC=C122058.7Standard non polar33892256
Indoleacetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=CC=C122062.8Standard polar33892256
Indoleacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=C[NH]C2=CC=CC=C122226.3Semi standard non polar33892256
Indoleacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=C[NH]C2=CC=CC=C122024.8Standard non polar33892256
Indoleacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=C[NH]C2=CC=CC=C122475.0Standard polar33892256
Indoleacetaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CC=O)C2=CC=CC=C212049.0Semi standard non polar33892256
Indoleacetaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CC=O)C2=CC=CC=C211959.3Standard non polar33892256
Indoleacetaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CC=O)C2=CC=CC=C212206.2Standard polar33892256
Indoleacetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122544.0Semi standard non polar33892256
Indoleacetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122424.4Standard non polar33892256
Indoleacetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122294.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (1 TMS)splash10-0udi-3790000000-d0624211b87a8c0c6eb02014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (1 MEOX; 1 TMS)splash10-0fb9-1890000000-f47966a3402f39ffb15a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (1 MEOX; 1 TMS)splash10-0ufr-2890000000-4661feb288e5418df1242014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (2 TMS)splash10-0udi-1659000000-1539f9bfe6f3cc9b5cc22014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (2 TMS)splash10-0udi-1669000000-87b7c126c24be968871e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (3 TMS)splash10-0006-0910000000-f73cd81db2b9712b46612014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized)splash10-0udi-1490000000-614e405de09537fc4b352014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-c2d7214f3eaf0a20e8642017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-75194e386ef16f3f47b22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized)splash10-0udi-3790000000-d0624211b87a8c0c6eb02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized)splash10-0fb9-1890000000-f47966a3402f39ffb15a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized)splash10-0ufr-2890000000-4661feb288e5418df1242017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized)splash10-0udi-1659000000-1539f9bfe6f3cc9b5cc22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized)splash10-0udi-1669000000-87b7c126c24be968871e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized)splash10-0006-0910000000-f73cd81db2b9712b46612017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized)splash10-0udi-1490000000-614e405de09537fc4b352017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-0900000000-4528170aed93d1f2f6cf2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indoleacetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoleacetaldehyde LC-ESI-QTOF , negative-QTOFsplash10-0a7i-0900000000-3a12e240a01798e6d5152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoleacetaldehyde , negative-QTOFsplash10-0a4i-0900000000-0d6b7064551a83893c6e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoleacetaldehyde LC-ESI-QTOF , positive-QTOFsplash10-0159-0900000000-868e767ca141d74ec8882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoleacetaldehyde 20V, Negative-QTOFsplash10-0059-0900000000-dea5f8a3cd655d34e7272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoleacetaldehyde 10V, Negative-QTOFsplash10-0a7i-0900000000-03eb4dd9323023a069702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoleacetaldehyde 40V, Negative-QTOFsplash10-004i-0900000000-ec1cff588ddd81294ce12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 10V, Positive-QTOFsplash10-03di-0900000000-a292bcb2abf1d20042962015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 20V, Positive-QTOFsplash10-03yl-0900000000-c9491489626575ac821c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 40V, Positive-QTOFsplash10-00l6-3900000000-c4a5850dd4b1a7da14e12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 10V, Negative-QTOFsplash10-0a4i-0900000000-8354b2e6155a5677c3532015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 20V, Negative-QTOFsplash10-0a4i-0900000000-2bd561638cdcf5535ba52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 40V, Negative-QTOFsplash10-014l-3900000000-bb8a2da37c41a8f5040e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 10V, Negative-QTOFsplash10-0api-0900000000-ab705375598dd738ce6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 20V, Negative-QTOFsplash10-014i-0900000000-924d3410f1e3855c23362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 40V, Negative-QTOFsplash10-014i-0900000000-74f0d61a0a5ca7d199252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 10V, Positive-QTOFsplash10-03ec-0900000000-f09223778d8ebf23f2f52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 20V, Positive-QTOFsplash10-001i-0900000000-474bb30e410332db437a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoleacetaldehyde 40V, Positive-QTOFsplash10-0fc0-3900000000-8e24fed06b1ae0ed20af2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified7.24 +/- 1.16 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013950
KNApSAcK IDC00000109
Chemspider ID778
KEGG Compound IDC00637
BioCyc IDINDOLE_ACETALDEHYDE
BiGG ID35561
Wikipedia LinkNot Available
METLIN ID6068
PubChem Compound800
PDB IDNot Available
ChEBI ID18086
Food Biomarker OntologyNot Available
VMH IDID3ACALD
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGray, Reed A. Preparation and properties of 3-indoleacetaldehyde. Archives of Biochemistry and Biophysics (1959), 81 480-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tottmar O, Hellstrom E: Aldehyde dehydrogenase in blood: a sensitive assay and inhibition by disulfiram. Pharmacol Biochem Behav. 1983;18 Suppl 1:103-7. [PubMed:6634824 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7