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fasedienol   Click here for help

GtoPdb Ligand ID: 14431

Synonyms: 4-androstadienol | [3β]-androsta-4,16-dien-3-ol | aloradine | PH-94B | PH94B
Compound class: Synthetic organic
Comment: Fasedienol (PH94B; VistaGen Therapeutics, formerly Pherin Pharmaceuticals) is a pherine, or vomeropherin [4]. Pherines are synthetic neuroactive steroids that are intended to acts as human pheromones via interactions with receptors on nasal chemosensory neurons within the vomeronasal organ (VNO). They are proposed to alter central nervous system activity (e.g., within the limbic amygdala and hypothalamus) through the olfactory system, and without crossing the blood-brain barrier, in turn inducing physiological, pharmacological and behavioural changes. Note that whilst intranasal administration of fasedienol in human subjects is reported to elicit biological and physiological responses [2-3], the functional capacity of vomeronasal receptors and the VNO in humans is open to debate [1,5-7].

fasedienol is commercially available from our sponsors

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 1
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 20.23
Molecular weight 272.43
XLogP 5.7
No. Lipinski's rules broken 1

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@]12C=CC[C@H]2[C@@H]3CCC4=C[C@H](CC[C@]4(C)[C@H]3CC1)O
Isomeric SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=C[C@H](CC[C@]34C)O
InChI InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,14-17,20H,4-8,10-11H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
InChI Key NYVFCEPOUVGTNP-DYKIIFRCSA-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
(3S,8S,9S,10R,13R,14S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
International Nonproprietary Names Click here for help
INN number INN
12019 fasedienol
Synonyms Click here for help
4-androstadienol | [3β]-androsta-4,16-dien-3-ol | aloradine | PH-94B | PH94B
Database Links Click here for help
ChEMBL Ligand CHEMBL5095042
DrugBank Ligand DB04968
PubChem CID 9925482
Search Google for chemical match using the InChIKey NYVFCEPOUVGTNP-DYKIIFRCSA-N
Search Google for chemicals with the same backbone NYVFCEPOUVGTNP
Search PubMed clinical trials fasedienol
Search PubMed titles fasedienol
Search PubMed titles/abstracts fasedienol
UniChem Compound Search for chemical match using the InChIKey NYVFCEPOUVGTNP-DYKIIFRCSA-N
UniChem Connectivity Search for chemical match using the InChIKey NYVFCEPOUVGTNP-DYKIIFRCSA-N

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MedChemExpress
Fasedienol (links to external site)
Cat. No. HY-145567