Indole-3-acetyl-beta-1-D-glucoside (BioCAD00000012406)
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Metabolite Card
Formula: C16H19NO7 (337.1161)
SMILES: OC[C@H]1O[C@@H](OC(=O)CC2=CNC3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O
Synonyms [en]
Indole-3-acetyl-beta-1-D-glucoside; 1-O-(indole-3-acetyl)-beta-1-D-glucose; indole-3-acetic acid beta-D-glucoside; 1-O-Indol-3-ylacetylglucose; Iaa-glucose; 1-O-indol-3-Ylacetyl-beta-D-glucose
Last reviewed on 2024-06-28.
Cite this Page
Indole-3-acetyl-beta-1-D-glucoside. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000012406). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
4-o-(indole-3-acetyl)-d-glucopyranose, also known as indole-3-acetyl-beta-1-D-glucose or B-D-glucopyranose, 1-(1h-indole-3-acetic acid), belongs to indole-3-acetic acid derivatives class of compounds. Those are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 4-o-(indole-3-acetyl)-d-glucopyranose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-o-(indole-3-acetyl)-d-glucopyranose can be found in corn, which makes 4-o-(indole-3-acetyl)-d-glucopyranose a potential biomarker for the consumption of this food product.
DBLinks
- CAS Registry Number: 52703-89-6
- PubChem CID: 440255
- ChEBI: 17990
- HMDB: HMDB0301785
- LipidMaps:
- KEGG: C04197
- BioCyc: CPD-1102
- NCBI MeSH: 1-O-indol-3-ylacetylglucose
- Wikipedia:
Other DBLinks
- CAS Registry Number: 19817-95-9
- CAS Registry Number: 52703-89-6
- PubChem: 440255
- ChEBI: ChEBI:17990
- HMDB: HMDB0301785
- KEGG: C04197
- BioCyc: CPD-1102
- NCBI MeSH: 1-O-indol-3-ylacetylglucose
- Metlin: METLIN_66132
- Coconut NaturalProduct: CNP0203780.1
- Coconut NaturalProduct: CNP0253017.1
- Coconut NaturalProduct: CNP0253017.2
Class / Ontology
- WishartLab ClassyFire: [Indolyl carboxylic acids and derivatives] Indolyl carboxylic acids and derivatives
- ChEBI: [CHEBI:17990] 1-O-(indol-3-ylacetyl)-beta-D-glucose
- Coconut NaturalProduct: [Simple indole alkaloids] Simple indole alkaloids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R03094 | 2.4.1.121 | UDPglucose:indole-3-acetate beta-D-glucosyltransferase |
| KEGG:R04333 | 2.3.1.72 | indole-3-acetyl-beta-1-D-glucoside:myo-inositol indoleacetyltransferase |
| Rhea:RHEA:14922 | 2.4.1.121 | (indol-3-yl)acetate + UDP-α-D-glucose => 1-O-(indol-3-ylacetyl)-β-D-glucose + UDP |
| Rhea:RHEA:14923 | 2.4.1.121 | 1-O-(indol-3-ylacetyl)-β-D-glucose + UDP => (indol-3-yl)acetate + UDP-α-D-glucose |
| Rhea:RHEA:14924 | 2.4.1.121 | (indol-3-yl)acetate + UDP-α-D-glucose <=> 1-O-(indol-3-ylacetyl)-β-D-glucose + UDP |
| Rhea:RHEA:21181 | 2.3.1.72 | 1-O-(indol-3-ylacetyl)-β-D-glucose + myo-inositol => indole-3-acetyl-1D-myo-inositol + D-glucose |
| Rhea:RHEA:21182 | 2.3.1.72 | indole-3-acetyl-1D-myo-inositol + D-glucose => 1-O-(indol-3-ylacetyl)-β-D-glucose + myo-inositol |
| Rhea:RHEA:21183 | 2.3.1.72 | 1-O-(indol-3-ylacetyl)-β-D-glucose + myo-inositol <=> indole-3-acetyl-1D-myo-inositol + D-glucose |
| BioCyc:RXN-3165 | 3.1.1.- | CPD-1102 + WATER --> INDOLE_ACETATE_AUXIN + Glucopyranose + PROTON |
| BioCyc:2.3.1.72-RXN | 2.3.1.72 | MYO-INOSITOL + CPD-1102 --> CPD-165 + Glucopyranose |
| BioCyc:2.4.1.121-RXN | 2.4.1.121 | CPD-12575 + INDOLE_ACETATE_AUXIN --> CPD-1102 + UDP |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:META_PWY-1782 | superpathway of indole-3-acetate conjugate biosynthesis |
| BioCyc:ARA_PWY-1782 | superpathway of indole-3-acetate conjugate biosynthesis |
| BioCyc:META_PWY-1921 | indole-3-acetate activation II |
| BioCyc:META_PWY-1741 | indole-3-acetate inactivation IX |
| Plant Reactome:R-OSA-2744345 | Metabolism and regulation |
| Plant Reactome:R-OSA-2744341 | Hormone signaling, transport, and metabolism |
| Plant Reactome:R-OSA-1119482 | IAA conjugation I |
| PlantCyc:ARA_PWY-1782 | superpathway of indole-3-acetate conjugate biosynthesis |
| PlantCyc:CORN_PWY-1921 | indole-3-acetate activation II |
| PlantCyc:ARA_PWY-1741 | indole-3-acetate inactivation IX |
| PlantCyc:CORN_PWY-1741 | indole-3-acetate inactivation IX |
| PlantCyc:CORN_PWY-1782 | superpathway of indole-3-acetate conjugate biosynthesis |
| PlantCyc:STORA_PWY-1782 | superpathway of indole-3-acetate conjugate biosynthesis |
| PlantCyc:STORA_PWY-1741 | indole-3-acetate inactivation IX |
| PlantCyc:PLANT_PWY-1921 | indole-3-acetate activation II |
| PlantCyc:PLANT_PWY-1782 | superpathway of indole-3-acetate conjugate biosynthesis |
| PlantCyc:LER_PWY-1782 | superpathway of indole-3-acetate conjugate biosynthesis |
| PlantCyc:LER_PWY-1741 | indole-3-acetate inactivation IX |
| PlantCyc:PLANT_PWY-1741 | indole-3-acetate inactivation IX |