22alpha-Hydroxy-5alpha-campestan-3-one (BioCAD00000003222)
Metabolite Card
Formula: C28H48O2 (416.3654)
SMILES: O[C@H]([C@H]([C@@]1([C@@]2(C([C@]3([C@@]([C@@]4([C@@](CC3)(CC(=O)CC4)[H])C)(CC2)[H])[H])CC1)C)[H])C)C[C@H](C(C)C)C
Synonyms [en]
22alpha-Hydroxy-5alpha-campestan-3-one; (22S)-22-hydroxy-5alpha-campestan-3-one; 22S-hydroxy-5alpha-campestan-3-one; (22S,24R)-22-Hydroxy-5alpha-ergostan-3-one; (5alpha,22S,24R)-22-hydroxyergostan-3-one; (5~{S},8~{S},9~{R},10~{R},13~{R},14~{S},17~{S})-17-[(1~{S},2~{S},4~{R})-2-hydroxy-1,4,5-trimethyl-hexyl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Last reviewed on 2024-06-28.
Cite this Page
22alpha-Hydroxy-5alpha-campestan-3-one. 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: BioCAD00000003222). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
A brassinosteroid that is 6-deoxocathasterone in which the hydroxy group at position 3 has been oxidised to the corresponding ketone." []
DBLinks
- CAS Registry Number: 208586-82-7
- PubChem CID: 46878488
- ChEBI: 181389
- HMDB: HMDB0012112
- LipidMaps: LMST01031117
- KEGG: C15797
- BioCyc: CPD-3946
- NCBI MeSH:
- Wikipedia:
Other DBLinks
- CAS Registry Number: 208586-82-7
- PubChem: 46878488
- ChEBI: ChEBI:181389
- ChEBI: ChEBI:59411
- HMDB: HMDB0012112
- LipidMaps: LMST01031117
- KEGG: C15797
- BioCyc: CPD-3946
- Metlin: METLIN_64135
- Coconut NaturalProduct: CNP0085009.1
- Coconut NaturalProduct: CNP0085009.2
Class / Ontology
- ChEBI: [CHEBI:181389] (5S,8R,9S,10S,13S,17R)-17-[(2S,3S,5R)-3-Hydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
- ChEBI: [CHEBI:59411] (5alpha,22S,24R)-22-hydroxyergostan-3-one
- Coconut NaturalProduct: [Cholestane steroids] Cholestane steroids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R07447 | 1.3.1.22 | 22alpha-hydroxy-5alpha-campestan-3-one:NADP+ delta4-oxidoreductase |
| KEGG:R07453 | 1.14.14.178 | 5alpha-campestan-3-one,NADPH---hemoprotein reductase:oxygen 22S-oxidoreductase (hydroxylating) |
| KEGG:R07472 | C15797<=>C15798 | |
| KEGG:R07788 | C15797<=>C16251 | |
| KEGG:R07791 | 1.14.14.147 | 22alpha-hydroxy-5alpha-campestan-3-one,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (C-23-hydroxylating) |
| Rhea:RHEA:27326 | 1.14.14.147 | (22S,24R)-22-hydroxy-5α-ergostan-3-one + reduced [NADPH—hemoprotein reductase] + O2 => 3-dehydro-6-deoxoteasterone + oxidized [NADPH—hemoprotein reductase] + H2O + H+ |
| Rhea:RHEA:27327 | 1.14.14.147 | 3-dehydro-6-deoxoteasterone + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => (22S,24R)-22-hydroxy-5α-ergostan-3-one + reduced [NADPH—hemoprotein reductase] + O2 |
| Rhea:RHEA:27328 | 1.14.14.147 | (22S,24R)-22-hydroxy-5α-ergostan-3-one + reduced [NADPH—hemoprotein reductase] + O2 <=> 3-dehydro-6-deoxoteasterone + oxidized [NADPH—hemoprotein reductase] + H2O + H+ |
| Rhea:RHEA:69976 | 6-deoxycathasterone + reduced [NADPH—hemoprotein reductase] + O2 => (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+ | |
| Rhea:RHEA:69977 | (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+ => 6-deoxycathasterone + reduced [NADPH—hemoprotein reductase] + O2 | |
| Rhea:RHEA:69978 | 6-deoxycathasterone + reduced [NADPH—hemoprotein reductase] + O2 <=> (22S,24R)-22-hydroxy-5α-ergostan-3-one + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+ | |
| Rhea:RHEA:69988 | (22S,24R)-22-hydroxy-5α-ergostan-3-one + NADP+ => (22S)-22-hydroxycampest-4-en-3-one + NADPH + H+ | |
| Rhea:RHEA:69989 | (22S)-22-hydroxycampest-4-en-3-one + NADPH + H+ => (22S,24R)-22-hydroxy-5α-ergostan-3-one + NADP+ | |
| Rhea:RHEA:69990 | (22S,24R)-22-hydroxy-5α-ergostan-3-one + NADP+ <=> (22S)-22-hydroxycampest-4-en-3-one + NADPH + H+ | |
| BioCyc:RXN-11532 | 1.1.99.- | Donor-H2 + CPD-3946 --> CPD-12493 + Acceptor |
| BioCyc:RXN-4228 | 1.1.-.- | CPD-3946 + Donor-H2 --> CPD-712 + Acceptor |
| BioCyc:RXN-11101 | 1.14.14.147 | CPD-3946 + OXYGEN-MOLECULE + Red-NADPH-Hemoprotein-Reductases --> CPD-717 + Ox-NADPH-Hemoprotein-Reductases + WATER |
| BioCyc:RXN-4229 | 1.3.1.- | PROTON + CPD-3945 + NADPH --> CPD-3946 + NADP |
| BioCyc:RXN-4230 | 1.14.14.- | CPD-709 + OXYGEN-MOLECULE + Red-NADPH-Hemoprotein-Reductases --> CPD-3946 + WATER + Ox-NADPH-Hemoprotein-Reductases |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:META_PWY-6544 | superpathway of C28 brassinosteroid biosynthesis |
| BioCyc:META_PWY-2582 | brassinosteroid biosynthesis II |
| Plant Reactome:R-OAU-2744345 | Metabolism and regulation |
| Plant Reactome:R-CME-2744341 | Hormone signaling, transport, and metabolism |
| Plant Reactome:R-MES-2744345 | Metabolism and regulation |
| Plant Reactome:R-MES-2744341 | Hormone signaling, transport, and metabolism |
| Plant Reactome:R-MES-1119456 | Brassinosteroid biosynthesis II |
| Plant Reactome:R-TDI-2744345 | Metabolism and regulation |
| Plant Reactome:R-DRO-2744345 | Metabolism and regulation |
| Plant Reactome:R-OGU-2744341 | Hormone signaling, transport, and metabolism |
| Plant Reactome:R-OGU-1119456 | Brassinosteroid biosynthesis II |
| Plant Reactome:R-GSU-1119456 | Brassinosteroid biosynthesis II |
| Plant Reactome:R-PTI-2744345 | Metabolism and regulation |
| Plant Reactome:R-PTI-2744341 | Hormone signaling, transport, and metabolism |
| Plant Reactome:R-PTI-1119456 | Brassinosteroid biosynthesis II |
| Plant Reactome:R-GMA-2744345 | Metabolism and regulation |
| Plant Reactome:R-PDA-2744345 | Metabolism and regulation |
| Plant Reactome:R-PVU-2744345 | Metabolism and regulation |
| Plant Reactome:R-CCA-2744341 | Hormone signaling, transport, and metabolism |
| Plant Reactome:R-CCA-1119456 | Brassinosteroid biosynthesis II |