5α-tetrahydrocorticosterone   Click here for help

GtoPdb Ligand ID: 13001

Synonyms: 5alpha-Tetrahydrocorticosterone | allotetrahydrocorticosterone
Compound class: Synthetic organic
Comment: 5α-tetrahydrocorticosterone (5αTHB) is an endogenous steroid with anti-inflammatory action [2]. In in vivo studies topically applied 5αTHB was less angiostatic and caused less skin thinning than the endogenous glucocorticoid/mineralocorticoid receptor agonists cortisol and corticosterone. It is proposed that 5αTHB's anti-inflammatory effects are mediated by mechanisms that are distinct from those of conventional glucocorticoids [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 77.76
Molecular weight 350.49
XLogP 2.98
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C[C@@]12CC[C@H](C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](C(=O)CO)[C@@]4(C)C[C@@H]([C@@H]31)O)O
Isomeric SMILES C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)C)O)O
InChI InChI=1S/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12-,13+,14-,15-,16+,17-,19+,20-,21-/m0/s1
InChI Key RHQQHZQUAMFINJ-NZTKVECHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
1-[(3R,5S,8S,9S,10S,11S,13S,14S,17S)-3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone
Synonyms Click here for help
5alpha-Tetrahydrocorticosterone | allotetrahydrocorticosterone
Database Links Click here for help
CAS Registry No. 600-63-5 (source: PubChem)
ChEBI CHEBI:89328
GtoPdb PubChem SID 485206122
LIPID MAPS LMST02030142
PubChem CID 101790
Search Google for chemical match using the InChIKey RHQQHZQUAMFINJ-NZTKVECHSA-N
Search Google for chemicals with the same backbone RHQQHZQUAMFINJ
UniChem Compound Search for chemical match using the InChIKey RHQQHZQUAMFINJ-NZTKVECHSA-N
UniChem Connectivity Search for chemical match using the InChIKey RHQQHZQUAMFINJ-NZTKVECHSA-N