25-Hydroxycholesterol (BioCAD00000003237)
Metabolite Card
Formula: C27H46O2 (402.3498)
SMILES: [H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
Synonyms [en]
25-hydroxycholesterol; 25-hydroxy-cholesterol; 25-OHC; 25-Hydroxycholest-5-en-3-ol; Cholest-5-ene-3beta,25-diol; cholest-5-en-3beta,25-diol
Last reviewed on 2024-06-28.
Cite this Page
25-Hydroxycholesterol. 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: BioCAD00000003237). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
25-Hydroxycholesterol is steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). It also induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases. 25-Hydroxycholesterol also enhances Interleukin-1 beta (IL-1beta-induced) IL-8 production.(PMID: 17086498). 25-hydroxycholesterol is endogenously produced from cholesterol at early time intervals after cholesterol ingestion. It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge.
DBLinks
- CAS Registry Number: 2140-46-7
- PubChem CID: 53477807
- ChEBI: 42977
- HMDB: HMDB0006247
- LipidMaps: LMST01010018
- KEGG: C15519
- BioCyc: CPD-7285
- NCBI MeSH: 25-hydroxycholesterol
- Wikipedia: 25-Hydroxycholesterol
Other DBLinks
- CAS Registry Number: 2140-46-7
- PubChem: 53477807
- PubChem: 65094
- ChEBI: ChEBI:37616
- ChEBI: ChEBI:42977
- HMDB: HMDB0006247
- HMDB: HMDB06247
- LipidMaps: LMST01010018
- KEGG: C15519
- BioCyc: CPD-7285
- NCBI MeSH: 25-hydroxycholesterol
- Wikipedia: 25-Hydroxycholesterol
- DrugBank: DB04705
- RefMet: RM0135645
- MoNA: BAF_UVA_POS000467
- MoNA: BAF_UVA_POS000579
- MoNA: MoNA016822
- Metlin: METLIN_3899
- Coconut NaturalProduct: CNP0266481.1
- Coconut NaturalProduct: CNP0266481.2
Class / Ontology
- WishartLab ClassyFire: [Cholestane steroids] Cholestane steroids
- RefMet: [Oxysterols] Oxysterols
- LipidMaps: [Cholesterol and derivatives [ST0101]] Cholesterol and derivatives [ST0101]
- ChEBI: [CHEBI:42977] 25-hydroxycholesterol
- Coconut NaturalProduct: [Cholestane steroids] Cholestane steroids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R07209 | 1.14.14.29 | cholest-5-ene-3beta,25-diol,[NADPH---hemoprotein reductase]:oxygen oxidoreductase (7alpha-hydroxylating) |
| KEGG:R07218 | 1.14.99.38 | cholesterol,hydrogen-donor:oxygen oxidoreductase (25-hydroxylating) |
| Rhea:RHEA:21105 | 1.14.99.38 | cholesterol + AH2 + O2 => 25-hydroxycholesterol + A + H2O |
| Rhea:RHEA:21106 | 1.14.99.38 | 25-hydroxycholesterol + A + H2O => cholesterol + AH2 + O2 |
| Rhea:RHEA:21107 | 1.14.99.38 | cholesterol + AH2 + O2 <=> 25-hydroxycholesterol + A + H2O |
| Rhea:RHEA:24309 | 1.14.14.29 | 25-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 => 7α,25-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ |
| Rhea:RHEA:24310 | 1.14.14.29 | 7α,25-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => 25-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 |
| Rhea:RHEA:24311 | 1.14.14.29 | 25-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 <=> 7α,25-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ |
| Rhea:RHEA:46133 | cholesterol + NADPH + O2 + H+ => 25-hydroxycholesterol + NADP+ + H2O | |
| Rhea:RHEA:46134 | 25-hydroxycholesterol + NADP+ + H2O => cholesterol + NADPH + O2 + H+ | |
| Rhea:RHEA:46135 | cholesterol + NADPH + O2 + H+ <=> 25-hydroxycholesterol + NADP+ + H2O | |
| Rhea:RHEA:50257 | cholesterol + reduced [NADPH—hemoprotein reductase] + O2 => 25-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ | |
| Rhea:RHEA:50258 | 25-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => cholesterol + reduced [NADPH—hemoprotein reductase] + O2 | |
| Rhea:RHEA:50259 | cholesterol + reduced [NADPH—hemoprotein reductase] + O2 <=> 25-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ | |
| BioCyc:RXN-19741 | 1.17.99.10 | CHOLESTEROL + WATER + Acceptor --> CPD-7285 + Donor-H2 |
| BioCyc:1.14.99.38-RXN | 1.14.99.38 | CHOLESTEROL + Donor-H2 + OXYGEN-MOLECULE --> CPD-7285 + Acceptor + WATER |
| BioCyc:RXN66-661 | 1.14.14.- | CHOLESTEROL + OXYGEN-MOLECULE + Red-NADPH-Hemoprotein-Reductases --> CPD-7285 + WATER + Ox-NADPH-Hemoprotein-Reductases |
| BioCyc:RXN-7980 | 1.14.14.29 | CPD-7285 + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> CPD-7286 + Ox-NADPH-Hemoprotein-Reductases + WATER |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| PathBank:SMP0120468 | Congenital Bile Acid Synthesis Defect Type III |
| PathBank:SMP0000318 | Congenital Bile Acid Synthesis Defect Type III |
| PathBank:SMP0120697 | Familial Hypercholanemia (FHCA) |
| PathBank:SMP0120463 | Cerebrotendinous Xanthomatosis (CTX) |
| PathBank:SMP0120467 | Congenital Bile Acid Synthesis Defect Type II |
| PathBank:SMP0120495 | Zellweger Syndrome |
| PathBank:SMP0000035 | Bile Acid Biosynthesis |
| PathBank:SMP0000314 | Congenital Bile Acid Synthesis Defect Type II |
| PathBank:SMP0000315 | Cerebrotendinous Xanthomatosis (CTX) |
| PathBank:SMP0087329 | Bile Acid Biosynthesis |
| PathBank:SMP0120652 | 27-Hydroxylase Deficiency |
| PathBank:SMP0120688 | Congenital Bile Acid Synthesis Defect Type III |
| PathBank:SMP0120477 | Familial Hypercholanemia (FHCA) |
| PathBank:SMP0000317 | Familial Hypercholanemia (FHCA) |
| PathBank:SMP0087236 | Bile Acid Biosynthesis |
| PathBank:SMP0120683 | Cerebrotendinous Xanthomatosis (CTX) |
| PathBank:SMP0120687 | Congenital Bile Acid Synthesis Defect Type II |
| PathBank:SMP0120715 | Zellweger Syndrome |
| PathBank:SMP0120871 | 27-Hydroxylase Deficiency |
| PathBank:SMP0000316 | Zellweger Syndrome |