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Compound Detail

CHEMBL2354444

PIRARUBICIN
🧪 Phase III
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🧪 Phase III
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O[C@@H]2CCCCO2)[C@H](C)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2354444
Name PIRARUBICIN
Phase Phase III
Structure Type MOL
InChI Key KMSKQZKKOZQFFG-YXRRJAAWSA-N

Known Names

Adriamycin, tetrahydropyranyl Pirarubicin Pirarubicina Pirarubicine Theprubicin Thp-adm
4
Targets
19
Activities
1
Assay Types
0
PK Parameters
20
Publications
6
Known Names
6
Indications

Molecular Properties

627.6
MW (Da)
1.55
ALogP
13
HBA
5
HBD
204.3
PSA (Ų)
0.24
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -rubicin

Extended Properties

Molecular Formula C32H37NO12
MW 627.64
Aromatic Rings 2
Heavy Atoms 45
NP-Likeness 1.51

Indications

Breast Neoplasms Carcinoma, Hepatocellular Neoplasms Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Sarcoma

ATC Classification

L01DB08
pirarubicin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 19 meas. best 8.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.2 6.3113 6.3 16
L5178Y
CHEMBL614720
 IC50 7.64 7.64 23.0 1
MUS81-ECE1
CHEMBL5465380
 IC50 6.1 6.1 790.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 5.9 5.9 1257.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 6.3 nM 8.2 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Unchecked IC50 = 22.0 nM 7.66 Antiproliferative activity against mouse MB49 cells assessed as reduction in cel... 31759851
Unchecked IC50 = 22.0 nM 7.66 Antiproliferative activity against C3H mouse MBT2 cells assessed as reduction in... 31759851
L5178Y IC50 = 23.0 nM 7.64 Antiproliferative activity against mouse L5178Y cells assessed as reduction in c... 31759851
Unchecked IC50 = 51.43 nM 7.29 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -
Unchecked IC50 = 79.5 nM 7.1 PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of ass... -
Unchecked IC50 = 80.63 nM 7.09 PubChem BioAssay. Increased HeLa cells with 4N DNA content-IC50. (Class of ass... -
MUS81-ECE1 IC50 = 790.0 nM 6.1 Inhibition of human GST-tagged MUS81-ECE1 expressed in Escherichia coli BL21(DE3... 37352577
Unchecked IC50 = 910.7 nM 6.04 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 994.89 nM 6.0 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture nuclear area decrease (vi... -
Unchecked IC50 = 1009.57 nM 6.0 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Histone deacetylase 6 IC50 = 1257.0 nM 5.9 Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi... -
Unchecked IC50 = 1275.14 nM 5.89 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 1746.34 nM 5.76 PubChem BioAssay. Increased HeLa cells in S-phase-IC50. (Class of assay: confi... -
Unchecked IC50 = 2012.66 nM 5.7 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Unchecked IC50 = 3948.8 nM 5.4 PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 ce... -
Unchecked IC50 = 7821.96 nM 5.11 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 8951.63 nM 5.05 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 9261.7 nM 5.03 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
33691794 10.1186/s13148-021-01037-1 A549 4
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
31759851 10.1016/j.bmcl.2019.126744 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
2296017 10.1021/jm00163a028 L1210 2
2296017 10.1021/jm00163a028 NON-PROTEIN TARGET 2
2296017 10.1021/jm00163a028 HT-29 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent noradrenaline transporter 1
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine