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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/)
Bioactivity Comments
In experiments using fasedienol delivered directly to the vomeronasal organ (VMO) pit of anxious human subjects, and measuring electrovomerogram amplitude (i.e., VMO-receptor-mediated activation by fasedienol), an EC50 of 1 nM was determined [4]. This does not however identify specific receptors for the fasedienol-mediated activity.