9-cis-Retinoic acid (BioCAD00000005608)
Metabolite Card
Formula: C20H28O2 (300.2089)
SMILES: C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C\C(O)=O
Synonyms [en]
9-cis-retinoic acid; alitretinoin; Panretin; alitretinoinum; 9(Z)-Retinoic acid; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
Last reviewed on 2024-06-28.
Cite this Page
9-cis-Retinoic acid. 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: BioCAD00000005608). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
9-cis-Retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as a ligand for two classes of ligand-dependent transcription factors: the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). all-trans-Retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable (PMID: 9115228).
DBLinks
- CAS Registry Number: 5300-03-8
- PubChem CID: 449171
- ChEBI: 50648
- HMDB: HMDB0002369
- LipidMaps: LMPR01090022
- KEGG: C15493
- BioCyc:
- NCBI MeSH: Alitretinoin
- Wikipedia: Alitretinoin
Other DBLinks
- CAS Registry Number: 5300-03-8
- PubChem: 449171
- ChEBI: ChEBI:50648
- HMDB: HMDB0002369
- LipidMaps: LMPR01090022
- KEGG: C15493
- NCBI MeSH: Alitretinoin
- Wikipedia: Alitretinoin
- DrugBank: DB00523
- RefMet: RM0020394
- Metlin: METLIN_41515
- Coconut NaturalProduct: CNP0209779.0
Class / Ontology
- WishartLab ClassyFire: [Retinoids] Retinoids
- RefMet: [Retinoids] Retinoids
- LipidMaps: [Retinoids [PR0109]] Retinoids [PR0109]
- ChEBI: [CHEBI:50648] 9-cis-retinoic acid
- Coconut NaturalProduct: [Apocarotenoids (β-)] Apocarotenoids (β-)
| ID | EC Number | Name |
|---|---|---|
| KEGG:R08384 | 1.2.3.1 | retinal:oxygen oxidoreductase |
| KEGG:R08385 | 1.2.1.36 | retinal:NAD+ oxidoreductase |
Taxonomy Source
- Anarrhinum pedatum [ncbi taxid: 2500742]
- Genipa americana [ncbi taxid: 58486]
- Hericium erinaceus [ncbi taxid: 91752]
- Homo sapiens [ncbi taxid: 9606]
- Panax notoginseng [ncbi taxid: 44586]
Pathway Synthetic
| pathway id | name |
|---|---|
| Reactome:R-BTA-1430728 | Metabolism |
| Reactome:R-BTA-211945 | Phase I - Functionalization of compounds |
| Reactome:R-CEL-5362517 | Signaling by Retinoic Acid |
| Reactome:R-CFA-162582 | Signaling Pathways |
| Reactome:R-CFA-5362517 | Signaling by Retinoic Acid |
| Reactome:R-CFA-1430728 | Metabolism |
| Reactome:R-DRE-5365859 | RA biosynthesis pathway |
| Reactome:R-DRE-211897 | Cytochrome P450 - arranged by substrate type |
| Reactome:R-DRE-211916 | Vitamins |
| Reactome:R-DDI-5365859 | RA biosynthesis pathway |
| Reactome:R-GGA-5362517 | Signaling by Retinoic Acid |
| Reactome:R-HSA-211859 | Biological oxidations |
| Reactome:R-HSA-5362517 | Signaling by Retinoic Acid |
| Reactome:R-HSA-1643685 | Disease |
| Reactome:R-MMU-1430728 | Metabolism |
| Reactome:R-MMU-211859 | Biological oxidations |
| Reactome:R-MMU-162582 | Signaling Pathways |
| Reactome:R-RNO-211945 | Phase I - Functionalization of compounds |
| Reactome:R-RNO-162582 | Signaling Pathways |
| Reactome:R-RNO-9006931 | Signaling by Nuclear Receptors |