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Compound Detail

CHEMBL274070

9-AMINOCAMPTOTHECIN
🧪 Phase II
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🧪 Phase II
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(N)cccc3nc2-1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL274070
Name 9-AMINOCAMPTOTHECIN
Phase Phase II
Structure Type MOL
InChI Key FUXVKZWTXQUGMW-FQEVSTJZSA-N

Known Names

9-amino-20(s)-camptothecin 9-aminocamptothecin Aminocamptothecin NSC-603071
10
Targets
16
Activities
2
Assay Types
7
PK Parameters
20
Publications
4
Known Names
11
Indications
1
Mechanisms

Molecular Properties

363.4
MW (Da)
1.66
ALogP
7
HBA
2
HBD
107.4
PSA (Ų)
0.39
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C20H17N3O4
MW 363.37
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 1.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA topoisomerase I inhibitor INHIBITOR DNA topoisomerase 1 ✓ ✓

Indications

Esophageal Neoplasms Kidney Neoplasms Lung Neoplasms Lymphoma Ovarian Neoplasms Ovarian Neoplasms Peritoneal Neoplasms Stomach Neoplasms Leukemia, Myeloid, Acute Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma

Activity Summary

IC50 15 meas. best 9.0
EC50 1 meas. best 8.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ADMET
CHEMBL612558
 IC50 9.0 8.025 1.0 2
HepG2
CHEMBL395
 IC50 8.46 8.46 3.5 1
COLO 205
CHEMBL614561
 IC50 8.18 8.18 6.6 1
BJ
CHEMBL614358
 EC50 8.14 8.14 7.2 1
HT-29
CHEMBL384
 IC50 8.13 8.13 7.4 1
NCI-H928
CHEMBL614785
 IC50 8.1 8.1 7.9 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.07 8.07 8.5 1
L1210
CHEMBL386
 IC50 7.92 7.9067 12.0 3
DNA topoisomerase 1
CHEMBL1781
 IC50 6.96 6.03 110.0 3
Unchecked
CHEMBL612545
 IC50 6.21 5.715 620.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 6.5 mL.min-1.kg-1 Homo sapiens
Fu 0.003 - Homo sapiens
KE 5.97 - Mus musculus
MRT 5.6 hr Homo sapiens
T1/2 0.2983 hr -
T1/2 0.39 hr -
T1/2 7.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ADMET IC50 = 1.0 nM 9.0 Cytotoxicity against mouse bone marrow cell by CFU-GM assay 21341674
HepG2 IC50 = 3.5 nM 8.46 Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]... 10479293
COLO 205 IC50 = 6.6 nM 8.18 Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]... 10479293
BJ EC50 = 7.18 nM 8.14 PUBCHEM_BIOASSAY: Fluorescence Cell-Based Dose Response to Characterize Compound... -
HT-29 IC50 = 7.4 nM 8.13 Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]... 10479293
NCI-H928 IC50 = 7.9 nM 8.1 Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]... 10479293
NON-PROTEIN TARGET IC50 = 8.5 nM 8.07 Cytotoxicity expressed as the concentration that inhibited incorporation of [3H]... 10479293
L1210 IC50 = 12.0 nM 7.92 Inhibitory activity in mice bearing L1210 leukemia 1846923
L1210 IC50 = 12.7 nM 7.9 Compound was tested in vitro for cytotoxicity against L1210 murine leukemia cell... -
L1210 IC50 = 12.7 nM 7.9 Concentration required to inhibit 50% of cell growth in L1210 murine leukemia ce... -
ADMET IC50 = 90.0 nM 7.05 Cytotoxicity against human bone marrow cell by CFU-GM assay 21341674
DNA topoisomerase 1 IC50 = 110.0 nM 6.96 Inhibition of Topoisomerase I by cleavage complex formation in human HL-60 cells 8410981
Unchecked IC50 = 620.0 nM 6.21 PUBCHEM_BIOASSAY: Dose Response selectivity of uHTS chemical inhibitors of T-cel... -
DNA topoisomerase 1 IC50 = 1800.0 nM 5.75 Concentration required to inhibit 50% relaxation of 250 ng of SV40 DNA obtained ... -
DNA topoisomerase 1 IC50 = 4200.0 nM 5.38 Compound was tested in vitro for inhibition of topoisomerase I. -
Unchecked IC50 = 6020.0 nM 5.22 PUBCHEM_BIOASSAY: Dose response counterscreen of uHTS chemical inhibitors of T-c... -

Literature References

PubMed DOI Target Context # Activities
8410981 10.1021/jm00070a013 Mus musculus 6
3783593 10.1021/jm00161a035 P338 5
21341674 10.1021/jm101354u ADMET 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
18426954 10.1124/dmd.108.020479 ADMET 4
3656353 10.1021/jm00393a016 Mus musculus 3
3656353 10.1021/jm00393a016 L1210 2
8289200 10.1021/jm00027a005 ADMET 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
11309344 - Broad substrate specificity ATP-binding cassette transporter ABCG2 2
- 10.1016/0960-894X(96)00083-2 Mus musculus 2
10479293 10.1021/jm990124q No relevant target 2
1846923 10.1021/jm00105a017 Mus musculus 2
12161136 10.1016/s0960-894x(02)00388-8 IGROV-1 1
12161136 10.1016/s0960-894x(02)00388-8 NCI-H226 1
12161136 10.1016/s0960-894x(02)00388-8 A498 1
12161136 10.1016/s0960-894x(02)00388-8 M19-MEL 1
12161136 10.1016/s0960-894x(02)00388-8 MCF7 1
- 10.1016/0960-894X(96)00083-2 DNA topoisomerase 1 1

Data from ChEMBL 36 via Core Engine