Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Cholesterol sulfate
- DrugBank Accession Number
- DB01990
- Background
Component of human seminal plasma & spermatozoa.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Cholesterol sulfate (DB01990)
- Weight
- Average: 466.717
Monoisotopic: 466.31168065 - Chemical Formula
- C27H46O4S
- Synonyms
- Cholest-5-en-3beta-ol sulfate
- Cholesterol 3-sulfate
- Cholesterol 3-sulphate
- Cholesterol hydrogen sulfate
- Cholesterol hydrogen sulphate
- Cholesterol sulphate
- Cholesterol-Sulfate
- Cholesteryl sulphate
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UNuclear receptor ROR-alpha Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Cholestane steroids
- Direct Parent
- Cholesterols and derivatives
- Alternative Parents
- Delta-5-steroids / Sulfated steroids / Sulfuric acid monoesters / Alkyl sulfates / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic homopolycyclic compound / Alkyl sulfate / Cholesterol / Delta-5-steroid / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organic sulfuric acid or derivatives / Organooxygen compound / Sulfate-ester
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- steroid sulfate (CHEBI:41321) / Sulfates (LMST05020016)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- KU576NT9O9
- CAS number
- 1256-86-6
- InChI Key
- BHYOQNUELFTYRT-DPAQBDIFSA-N
- InChI
- InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
- IUPAC Name
- [(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid
- SMILES
- [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCCC(C)C
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000653
- KEGG Compound
- C18043
- PubChem Compound
- 65076
- PubChem Substance
- 46507419
- ChemSpider
- 58586
- ChEBI
- 41321
- ChEMBL
- CHEMBL1231592
- ZINC
- ZINC000012494196
- PDBe Ligand
- C3S
- Wikipedia
- Cholesterol_sulfate
- PDB Entries
- 1s0x / 2hka / 2mzi / 2q9f / 4tri / 5kwy / 5nti / 7fjf
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Not Yet Recruiting Treatment Invasive Fungal Infections 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 7.48e-05 mg/mL ALOGPS logP 3.27 ALOGPS logP 7.17 Chemaxon logS -6.8 ALOGPS pKa (Strongest Acidic) -1.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 63.6 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 130.61 m3·mol-1 Chemaxon Polarizability 56.55 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9913 Blood Brain Barrier + 0.9462 Caco-2 permeable - 0.6358 P-glycoprotein substrate Substrate 0.5 P-glycoprotein inhibitor I Inhibitor 0.7362 P-glycoprotein inhibitor II Non-inhibitor 0.7758 Renal organic cation transporter Non-inhibitor 0.8077 CYP450 2C9 substrate Non-substrate 0.8231 CYP450 2D6 substrate Non-substrate 0.8288 CYP450 3A4 substrate Substrate 0.7015 CYP450 1A2 substrate Non-inhibitor 0.8072 CYP450 2C9 inhibitor Non-inhibitor 0.8089 CYP450 2D6 inhibitor Non-inhibitor 0.8779 CYP450 2C19 inhibitor Non-inhibitor 0.7464 CYP450 3A4 inhibitor Non-inhibitor 0.884 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5501 Ames test Non AMES toxic 0.548 Carcinogenicity Non-carcinogens 0.5486 Biodegradation Not ready biodegradable 0.9838 Rat acute toxicity 2.4505 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.7589 hERG inhibition (predictor II) Non-inhibitor 0.5388
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 232.6348203 predictedDarkChem Lite v0.1.0 [M-H]- 229.0146178 predictedDarkChem Standard v0.1.0 [M-H]- 239.5586203 predictedDarkChem Lite v0.1.0 [M-H]- 228.65628 predictedDeepCCS 1.0 (2019) [M+H]+ 230.55168 predictedDeepCCS 1.0 (2019) [M+Na]+ 236.67984 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Key regulator of embryonic development, cellular differentiation, immunity, circadian rhythm as well as lipid, steroid, xenobiotics and glucose metabolism. Considered to have intrinsic transcriptional activity, have some natural ligands like oxysterols that act as agonists (25-hydroxycholesterol) or inverse agonists (7-oxygenated sterols), enhancing or repressing the transcriptional activity, respectively. Recruits distinct combinations of cofactors to target genes regulatory regions to modulate their transcriptional expression, depending on the tissue, time and promoter contexts. Regulates genes involved in photoreceptor development including OPN1SW, OPN1SM and ARR3 and skeletal muscle development with MYOD1. Required for proper cerebellum development (PubMed:29656859). Regulates SHH gene expression, among others, to induce granule cells proliferation as well as expression of genes involved in calcium-mediated signal transduction. Regulates the circadian expression of several clock genes, including CLOCK, BMAL1, NPAS2 and CRY1. Competes with NR1D1 for binding to their shared DNA response element on some clock genes such as BMAL1, CRY1 and NR1D1 itself, resulting in NR1D1-mediated repression or RORA-mediated activation of clock genes expression, leading to the circadian pattern of clock genes expression. Therefore influences the period length and stability of the clock. Regulates genes involved in lipid metabolism such as apolipoproteins APOA1, APOA5, APOC3 and PPARG. In liver, has specific and redundant functions with RORC as positive or negative modulator of expression of genes encoding phase I and phase II proteins involved in the metabolism of lipids, steroids and xenobiotics, such as CYP7B1 and SULT2A1. Induces a rhythmic expression of some of these genes. In addition, interplays functionally with NR1H2 and NR1H3 for the regulation of genes involved in cholesterol metabolism. Also involved in the regulation of hepatic glucose metabolism through the modulation of G6PC1 and PCK1. In adipose tissue, plays a role as negative regulator of adipocyte differentiation, probably acting through dual mechanisms. May suppress CEBPB-dependent adipogenesis through direct interaction and PPARG-dependent adipogenesis through competition for DNA-binding. Downstream of IL6 and TGFB and synergistically with RORC isoform 2, is implicated in the lineage specification of uncommitted CD4(+) T-helper (T(H)) cells into T(H)17 cells, antagonizing the T(H)1 program. Probably regulates IL17 and IL17F expression on T(H) by binding to the essential enhancer conserved non-coding sequence 2 (CNS2) in the IL17-IL17F locus. Involved in hypoxia signaling by interacting with and activating the transcriptional activity of HIF1A. May inhibit cell growth in response to cellular stress. May exert an anti-inflammatory role by inducing CHUK expression and inhibiting NF-kappa-B signaling
- Specific Function
- beta-catenin binding
- Gene Name
- RORA
- Uniprot ID
- P35398
- Uniprot Name
- Nuclear receptor ROR-alpha
- Molecular Weight
- 58974.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52