TETRAHYDROPALMATINE

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Search structure


Synonyms	(-)-corydalis b (-)-rotundine (-)-tetrahydropalmatine Caseanine Gindarine Hyndarine L-Tetrahydropalmatine Levo-tetrahydropalmatine Rotundine Tetrahydropalmatine Tetrahydropalmatine l-form Tetrahydropalmatine, (-)- Tetrahydropalmatine, dl- Tetrahydropalmatine, l-
Status
Molecule Category	UNKNOWN
UNII	3X69CO5I79


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

Structure


InChI Key	AEQDJSLRWYMAQI-KRWDZBQOSA-N
Smiles	COc1cc2c(cc1OC)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2
InChI	InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H25NO4
Molecular Weight	355.43
AlogP	3.38
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	4.0
Polar Surface Area	40.16
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	26.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of HIV1 RT	Human immunodeficiency virus 1	200.0 ug.mL-1
Inhibition of Human immunodeficiency virus 1 NL4.3 reverse transcriptase activity at 200 ug/ml	Human immunodeficiency virus 1	25.0 %
Inhibition of tissue factor procoagulant activity in LPS-stimulated human THP1 cells preincubated for 1 hr before LPS addition measured after 5 hrs	Homo sapiens	22.78 nM
Displacement of [3H]SCH23390 from dopamine D1 receptor (unknown origin) expressed in human HEK293 cells by liquid scintillation counter	Homo sapiens	231.0 nM
Inhibition of [3H]Ketanserin binding to 5-HT2A receptor (unknown origin) expressed in HEK293 cells at 10 uM by liquid scintillation counter relative to control	Homo sapiens	33.0 %
Inhibition of [3H]8-OH-DPAT binding to 5-HT1A receptor (unknown origin) expressed in HEK293 cells at 10 uM by liquid scintillation counter relative to control	Homo sapiens	84.9 %
Inhibition of [3H]spiperone binding to dopamine D2 receptor (unknown origin) expressed in human HEK293 cells at 10 uM by liquid scintillation counter relative to control	Homo sapiens	85.4 %
Inhibition of [3H]SCH23390 binding to dopamine D1 receptor (unknown origin) expressed in human HEK293 cells at 10 uM by liquid scintillation counter relative to control	Homo sapiens	96.9 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	186.7 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	106.92 %
Antagonist activity at human full-length N-terminal SNAP-tagged alpha1A adrenoceptor expressed in HEK293 cells assessed as inhibition of agonist-induced calcium mobilization at 10 uM preincubated for 10 mins followed by agonist addition by fluo-4 AM dye-based assay relative to control	Homo sapiens	41.2 %
Displacement of [3H]SCH23390 from human 3HA-tagged dopamine D1 receptor expressed in HEK293 cells after 1 hr	Homo sapiens	153.0 nM
Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in HEK293 cells after 1 hr	Homo sapiens	305.0 nM
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	-11.62 %
Antagonist activity at D2 receptor (unknown origin) expressed in CHOK1 cells assessed as inhibition of dopamine-induced calcium flux preincubated for 60 mins at 37 degC followed by 15 mins incubation under room temperature and subsequent dopamine addition measured after 20 secs for 100 secs by calcium-4 dye based FLIPR assay	Homo sapiens	450.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	7.96 %
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	0.09 %		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	0.09 %

Related Entries

Cross References

Resources	Reference
ChEBI	16563
ChEMBL	CHEMBL487182
DrugBank	DB12093
FDA SRS	3X69CO5I79
KEGG	C02890
PubChem	72301
SureChEMBL	SCHEMBL230850
ZINC	ZINC000019535049

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).