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Compound Detail

CHEMBL481839

ESCHOLTZINE
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CN1[C@H]2Cc3cc4c(cc3[C@@H]1Cc1cc3c(cc12)OCO3)OCO4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL481839
Name ESCHOLTZINE
Phase Preclinical
Structure Type MOL
InChI Key PGINMPJZCWDQNT-GJZGRUSLSA-N
7
Targets
8
Activities
3
Assay Types
0
PK Parameters
7
Publications
0
Known Names

Molecular Properties

323.4
MW (Da)
2.97
ALogP
5
HBA
0
HBD
40.2
PSA (Ų)
0.75
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H17NO4
MW 323.35
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 0.77

Activity Summary

IC50 6 meas. best 5.06
EC50 1 meas. best 4.96
Ki 1 meas. best 5.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 5.22 5.22 6000.0 1
A549
CHEMBL392
 IC50 5.06 5.06 8709.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 EC50 4.96 4.96 11000.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.87 4.87 13400.0 1
KB
CHEMBL398
 IC50 4.77 4.77 17030.0 1
Unchecked
CHEMBL612545
 IC50 4.7 4.7 19800.0 1
MCF7
CHEMBL387
 IC50 4.58 4.58 26560.0 1
MDA-MB-231
CHEMBL400
 IC50 4.58 4.58 26130.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1A Ki = 6000.0 nM 5.22 Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in... 16562853
A549 IC50 = 8709.0 nM 5.06 Antiproliferative activity against human A549 cells after 72 hrs by SRB assay 28099003
5-hydroxytryptamine receptor 1A EC50 = 11000.0 nM 4.96 Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in... 16562853
Cytochrome P450 3A4 IC50 = 13400.0 nM 4.87 Inhibition of CYP3A4 16562853
KB IC50 = 17030.0 nM 4.77 Antiproliferative activity against human KB cells after 72 hrs by SRB assay 28099003
Unchecked IC50 = 19800.0 nM 4.7 Antiproliferative activity against human KBVIN cells after 72 hrs by SRB assay 28099003
MDA-MB-231 IC50 = 26130.0 nM 4.58 Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by SRB as... 28099003
MCF7 IC50 = 26560.0 nM 4.58 Antiproliferative activity against human MCF7 cells after 72 hrs by SRB assay 28099003

Literature References

PubMed DOI Target Context # Activities
28099003 10.1021/acs.jnatprod.6b01153 Unchecked 5
16562853 10.1021/np058114h 5-hydroxytryptamine receptor 1A 2
16562853 10.1021/np058114h Cytochrome P450 3A4 1
28099003 10.1021/acs.jnatprod.6b01153 A549 1
28099003 10.1021/acs.jnatprod.6b01153 MDA-MB-231 1
28099003 10.1021/acs.jnatprod.6b01153 MCF7 1
28099003 10.1021/acs.jnatprod.6b01153 KB 1

Data from ChEMBL 36 via Core Engine