Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL286494

HYPERICIN
🧪 Phase III
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
🧪 Phase III
Cc1cc(O)c2c(=O)c3c(O)cc(O)c4c5c(O)cc(O)c6c(=O)c7c(O)cc(C)c8c1c2c(c34)c(c78)c65
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL286494
Name HYPERICIN
Phase Phase III
Structure Type MOL
InChI Key BTXNYTINYBABQR-UHFFFAOYSA-N

Known Names

Hipericin Hypericin Hypericina Hypericine Hypericum red NSC-407313 SGX-301 SGX301
13
Targets
31
Activities
3
Assay Types
3
PK Parameters
20
Publications
8
Known Names
6
Indications

Molecular Properties

504.4
MW (Da)
5.08
ALogP
8
HBA
6
HBD
155.5
PSA (Ų)
0.12
QED
3
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Year 2022

Extended Properties

Molecular Formula C30H16O8
MW 504.45
Aromatic Rings 8
Heavy Atoms 38
NP-Likeness 0.61

Indications

Lymphoma, T-Cell, Cutaneous Mycosis Fungoides Psoriasis HIV Infections Lymphoma, T-Cell Photochemotherapy

Activity Summary

IC50 27 meas. best 6.82
EC50 2 meas. best 5.91
Ki 2 meas. best 7.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(3) dopamine receptor
CHEMBL234
 Ki 7.46 7.46 34.5 1
Unchecked
CHEMBL612545
 IC50 6.82 6.219 150.0 10
Unchecked
CHEMBL612545
 Ki 6.7 6.7 200.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 6.6 6.6 250.0 2
Corticotropin-releasing factor receptor 1
CHEMBL1800
 IC50 6.52 6.52 300.0 2
SARS-CoV-2
CHEMBL4303835
 EC50 5.91 4.99 1240.0 2
HaCaT
CHEMBL614392
 IC50 5.77 5.77 1700.0 1
Cystathionine beta-synthase
CHEMBL3399911
 IC50 5.51 5.51 3100.0 1
Glutathione reductase
CHEMBL4119
 IC50 5.43 5.43 3670.0 1
Alpha-synuclein
CHEMBL6152
 IC50 5.12 5.12 7500.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.06 5.06 8700.0 1
Cysteine protease ATG4B
CHEMBL1741221
 IC50 5.05 4.645 8900.0 2
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 5.0 5.0 10000.0 1
Dopamine beta-hydroxylase
CHEMBL3102
 IC50 4.68 4.68 21000.0 1
Thioredoxin reductase 2, mitochondrial
CHEMBL5086
 IC50 4.37 4.34 43151.9 2

Pharmacokinetic Data

Parameter Value Units Species
CL 0.13 mL.min-1.kg-1 Homo sapiens
MRT 32.0 hr Homo sapiens
T1/2 42.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(3) dopamine receptor Ki = 34.5 nM 7.46 Binding affinity to dopamine D3 receptor 20408551
Unchecked IC50 = 150.0 nM 6.82 Inhibition of porcine heart malate dehydrogenase preincubated for 5 min followed... 34812616
Unchecked Ki = 200.0 nM 6.7 Inhibition of rat small intestine GST using CDNB as substrate by spectrophotomet... 33290062
Unchecked IC50 = 200.0 nM 6.7 Inhibition of bovine lung sGC assessed as reduction in GMP level incubated for 2... 33290062
SARS-CoV-2 IC50 = 250.0 nM 6.6 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
SARS-CoV-2 IC50 = 250.0 nM 6.6 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
Corticotropin-releasing factor receptor 1 IC50 = 300.0 nM 6.52 Inhibition of CRF1 receptor 20408551
Corticotropin-releasing factor receptor 1 IC50 = 300.0 nM 6.52 Inhibition of recombinant CRF1 receptor expressed in CHO cells assessed as inhib... 20408551
Unchecked IC50 = 300.0 nM 6.52 Inhibition of porcine heart MDH using oxaloacetic acid as substrate preincubated... 38864383
Unchecked IC50 = 320.0 nM 6.5 Inhibition of bovine lung sGC assessed as reduction in GMP level incubated for 2... 33290062
Unchecked IC50 = 350.0 nM 6.46 Inhibition of bovine lung sGC assessed as reduction in GMP level incubated for 2... 33290062
Unchecked IC50 = 400.0 nM 6.4 Inhibition of human sGC expressed in HUVEC cells assessed as reduction in GMP le... 33290062
Unchecked IC50 = 400.0 nM 6.4 Inhibition of bovine lung sGC assessed as reduction in GMP level incubated for 2... 33290062
Unchecked IC50 = 700.0 nM 6.16 Inhibition of human sGC expressed in HUVEC cells assessed as reduction in GMP le... 33290062
SARS-CoV-2 EC50 = 1240.0 nM 5.91 Antiviral activity against SARS-CoV-2 38864383
HaCaT IC50 = 1700.0 nM 5.77 Antiproliferative (inhibition of cell growth) activity against HaCaT cells (huma... 9371243
Unchecked IC50 = 3000.0 nM 5.52 Inhibition of Hepatitis C virus NS3 helicase measured by fluorescence helicase a... 34153576
Cystathionine beta-synthase IC50 = 3100.0 nM 5.51 Inhibition of full-length GST-fused human CBS using cysteine/homocysteine as sub... 30108705
Glutathione reductase IC50 = 3670.0 nM 5.43 Inhibition of yeast glutathione reductase by spectrophotometry 21106380
Alpha-synuclein IC50 = 7500.0 nM 5.12 Inhibition of human alpha-synuclein filament formation expressed in Escherichia ... 30743095

Literature References

PubMed DOI Target Context # Activities
- 10.1016/S0960-894X(01)80357-7 Equine infectious anemia virus 14
33290062 10.1021/acs.jnatprod.0c00854 Unchecked 14
20408551 10.1021/np1000329 Rattus norvegicus 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
21106380 10.1016/j.bmc.2010.10.045 Thioredoxin reductase 1, cytoplasmic 5
18426954 10.1124/dmd.108.020479 ADMET 4
17291039 10.1021/np060309h Unchecked 4
17220400 10.1128/aac.00999-06 Streptococcus mutans 4
34812616 10.1021/acs.jmedchem.1c01547 Unchecked 4
38864383 10.1021/acs.jmedchem.4c00597 Unchecked 3
21106380 10.1016/j.bmc.2010.10.045 Thioredoxin reductase 2, mitochondrial 3
38864383 10.1021/acs.jmedchem.4c00597 No relevant target 3
38864383 10.1021/acs.jmedchem.4c00597 SARS-CoV-2 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 3
20408551 10.1021/np1000329 Corticotropin-releasing factor receptor 1 2
30108705 10.1039/C6MD00493H Cystathionine beta-synthase 2
20408551 10.1021/np1000329 Caco-2 2
- 10.6019/CHEMBL4495565 ADMET 2
9371243 10.1021/jm970292n HaCaT 2
9371243 10.1021/jm970292n Molecular identity unknown 2

Data from ChEMBL 36 via Core Engine