YOHIMBINE HYDROCHLORIDE

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Synonyms	NSC-19509 Prowess plain Yocon Yohimbine hcl Yohimbine hydrochloride
Status
Molecule Category	Salt-form
UNII	NB2E1YP49F
EPA CompTox	DTXSID40891272
Parent Compound:	YOHIMBINE


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	PIPZGJSEDRMUAW-VJDCAHTMSA-N
Smiles	COC(=O)[C@@H]1[C@H]2C[C@H]3c4[nH]c5ccccc5c4CCN3C[C@@H]2CC[C@@H]1O.Cl
InChI	InChI=1S/C21H26N2O3.ClH/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24;/h2-5,12,15,17-19,22,24H,6-11H2,1H3;1H/t12-,15-,17-,18-,19+;/m0./s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H27ClN2O3
Molecular Weight	390.91
AlogP	2.65
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	1.0
Polar Surface Area	65.56
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	26.0

Assay Description	Organism	Bioactivity	Reference
Displacement of [3H]MK-912 from adrenergic alpha2A receptor in HT29 cells	None	1.8 nM
Displacement of [3H]MK912 from adrenergic alpha-2B receptor expressed in COS7 cells	None	15.0 nM
Displacement of [3H]MK912 from adrenergic Alpha-2C receptor in HepG2 cells	None	1.9 nM
Displacement of [3H]MK9112 from human recombinant adrenergic alpha2A receptor expressed in insect Sf9 cells after 60 mins	Homo sapiens	3.67 nM
Displacement of radioligand from human adrenergic Alpha-2C receptor after 60 mins	Homo sapiens	27.1 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method	Electrophorus electricus	16.16 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method	Equus caballus	-2.5 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	81.24 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	113.34 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	58.63 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	17.9 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.17 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.17 %

Cross References

Resources	Reference
ChEMBL	CHEMBL537669
FDA SRS	NB2E1YP49F
PubChem	6169
SureChEMBL	SCHEMBL33955

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).