3β-OH   Click here for help

GtoPdb Ligand ID: 10537

Synonyms: (3β,5β,17β)-3-hydroxyandrostane-17-carbonitrile [1] | B260 [2]
Compound class: Synthetic organic
Comment: 3β-OH is a neuroactive steroid analogue that produces general anaesthetic/hypnotic effects in vivo, but without associated neurotoxicity [1]. It blocks presynaptic transmitter release without affecting major postsynaptic ligand-gated ion channels. The chemical structure of 3β-OH is based on that of progesterone, with an OH substitution at position 3, and a CN group substitution at position 3. This chemical structure is claimed as B260 in patent WO2015149066A1 [2]. Mechanistically, 3β-OH selectively targets T-type voltage-gated calcium channels (T-channels; Cav3.1, Cav3.2, and Cav3.3) to mediate its hypnotic activity. 3β-OH exhibits minimal activity towards voltage-gated Na+ and K+ currents, N-type and L-type Ca2+ currents [3-4] or currents generated via recombinant GABAA and NMDA channels [5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 44.02
Molecular weight 301.24
XLogP 5.94
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES N#CC1CCC2C1(C)CCC1C2CCC2C1(C)CCC(C2)O
Isomeric SMILES N#C[C@H]1CCC2[C@]1(C)CCC1C2CC[C@H]2[C@]1(C)CC[C@@H](C2)O
InChI InChI=1S/C20H31NO/c1-19-9-7-15(22)11-13(19)3-5-16-17-6-4-14(12-21)20(17,2)10-8-18(16)19/h13-18,22H,3-11H2,1-2H3/t13-,14-,15+,16?,17?,18?,19+,20-/m1/s1
InChI Key DVTDUTYENPZLFP-FXEFULGUSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3S,5R,10S,13S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile
Synonyms Click here for help
(3β,5β,17β)-3-hydroxyandrostane-17-carbonitrile [1] | B260 [2]
Database Links Click here for help
GtoPdb PubChem SID 387065619
PubChem CID 129257213
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