1.0 2020-02-10 19:45:26 UTC 2021-01-12 22:02:02 UTC BMDB0063668 BMDB63668 1H-Indole-3-carboxaldehyde Indole-3-carboxaldehyde (IAld or I3A), also known as 3-formylindole or 3-indolealdehyde, 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. I3A is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells. It stimulates the production of interleukin-22 which facilitates mucosal reactivity (PMID: 27102537). I3A is a microbially derived tryptophan metabolite produced by Clostridium and Lactobacillus (PMID: 30120222 , 27102537 ). I3A has also been found in the urine of patients with untreated phenylketonuria (PMID: 5073866). Outside of the human body, I3A has been detected, but not quantified in, several different foods, such as beans, Brussels sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make I3A a potential biomarker for the consumption of these foods.  1H-Indole-3-carboxaldehyde 3-Formylindole 3-Indolealdehyde 3-Indolecarbaldehyde 3-Indolecarboxaldehyde beta-Indolylaldehyde I3cho Indole-3-aldehyde Indole-3-carbaldehyde b-Indolylaldehyde Β-indolylaldehyde 3-Indolemethanal 1H-Indole-3-carbaldehyde 1H-Indole-3-carboxaldehde indol-3-Carbaldehyd indol-3-Carbaldehyde indol-3-Carboxaldehyde INDOLE-3-carboxyaldehyde Indole-3-carboxaldehyde 1H-Indol-3-yl carboxaldehyde 1H-Indole-3-aldehyde 1H-Indole-3-methanal 3-Formyl-1H-indole 3-Indolylformaldehyde I3A Indole-3-carboxylaldehyde Indole-3-formaldehyde C9H7NO 145.158 145.052763851 1H-indole-3-carbaldehyde indole-3-carboxaldehyde 487-89-8 O=CC1=CNC2=C1C=CC=C2 InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H OLNJUISKUQQNIM-UHFFFAOYSA-N 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. Organic compounds Organoheterocyclic compounds Indoles and derivatives Indoles Indoles Aryl-aldehydes Azacyclic compounds Benzenoids Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Substituted pyrroles Vinylogous amides Aldehyde Aromatic heteropolycyclic compound Aryl-aldehyde Azacycle Benzenoid Heteroaromatic compound Hydrocarbon derivative Indole Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyrrole Substituted pyrrole Vinylogous amide Aromatic heteropolycyclic compounds an indole-phytolexin heteroarenecarbaldehyde indoles logp 1.92 ALOGPS logs -1.77 ALOGPS logp 1.78 ChemAxon pka_strongest_acidic 13.54 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac 1H-indole-3-carbaldehyde ChemAxon average_mass 145.158 ChemAxon mono_mass 145.052763851 ChemAxon smiles O=CC1=CNC2=C1C=CC=C2 ChemAxon formula C9H7NO ChemAxon inchi InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H ChemAxon inchikey OLNJUISKUQQNIM-UHFFFAOYSA-N ChemAxon polar_surface_area 32.86 ChemAxon refractivity 43.73 ChemAxon polarizability 15 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::EiMs 1644 Specdb::MsIr 3662 Specdb::MsIr 3663 Specdb::MsIr 3664 Specdb::CMs 15249 Specdb::CMs 26846 Specdb::CMs 27360 Specdb::CMs 29057 Specdb::CMs 29721 Specdb::CMs 30359 Specdb::CMs 30360 Specdb::CMs 30832 Specdb::CMs 30833 Specdb::CMs 100436 Specdb::CMs 100437 Specdb::CMs 100438 Specdb::CMs 100439 Specdb::CMs 100440 Specdb::CMs 100441 Specdb::CMs 100442 Specdb::CMs 100443 Specdb::CMs 130831 Specdb::CMs 138565 Specdb::MsMs 13112 Specdb::MsMs 13113 Specdb::MsMs 13114 Specdb::MsMs 19784 Specdb::MsMs 19785 Specdb::MsMs 19786 Specdb::MsMs 439031 Specdb::MsMs 439032 Specdb::MsMs 439291 Specdb::MsMs 439292 Specdb::MsMs 445252 Specdb::MsMs 445253 Specdb::MsMs 445254 Specdb::MsMs 445255 Specdb::MsMs 447948 Specdb::MsMs 448228 Specdb::MsMs 2235804 Specdb::MsMs 2237551 Specdb::MsMs 2237902 Specdb::MsMs 2239695 Specdb::MsMs 2240022 Specdb::MsMs 2241669 Specdb::MsMs 2242145 Specdb::MsMs 2243745 Specdb::MsMs 2246352 Specdb::NmrOneD 3875 Specdb::NmrOneD 4145 Specdb::NmrOneD 110158 Specdb::NmrOneD 110159 Specdb::NmrOneD 110160 Specdb::NmrOneD 110161 Specdb::NmrOneD 110162 Specdb::NmrOneD 110163 Specdb::NmrOneD 110164 Specdb::NmrOneD 110165 Specdb::NmrOneD 110166 Specdb::NmrOneD 110167 Specdb::NmrOneD 110168 Specdb::NmrOneD 110169 Specdb::NmrOneD 110170 Specdb::NmrOneD 110171 Specdb::NmrOneD 110172 Specdb::NmrOneD 110173 Specdb::NmrOneD 110174 Specdb::NmrOneD 110175 Specdb::NmrOneD 110176 Specdb::NmrOneD 110177 FDB000934 9838 C00000112 10256 28238 I3A C08493 INDOLE-3-CARBOXALDEHYDE Indole-3-carboxaldehyde Zhang LS, Davies SS: Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions. Genome Med. 2016 Apr 21;8(1):46. doi: 10.1186/s13073-016-0296-x. 27102537 Kochen W, Buhner R, Otting W: [Identification of oxindole and 3-indolecarbaldehyde in the urine of patients with untreated phenylketonuria]. Hoppe Seylers Z Physiol Chem. 1972 Jul;353(7):1017-22. 5073866