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Compound Detail

CHEMBL36506

NOVOBIOCIN
💊 Approved Drug
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💊 Approved Drug
CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2C)OC1(C)C

Basic Information

ChEMBL ID CHEMBL36506
Name NOVOBIOCIN
Phase Approved
Structure Type MOL
InChI Key YJQPYGGHQPGBLI-KGSXXDOSSA-N
Therapeutic ✓ Yes

Known Names

Albamycin t Cathomycin Novobiocin Novobiocina Novobiocine
25
Targets
209
Activities
4
Assay Types
2
PK Parameters
20
Publications
5
Known Names
1
Indications

Molecular Properties

612.6
MW (Da)
3.63
ALogP
11
HBA
5
HBD
200.0
PSA (Ų)
0.18
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1964
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C31H36N2O11
MW 612.63
Aromatic Rings 3
Heavy Atoms 44
NP-Likeness 1.39

Indications

Osteomyelitis

Activity Summary

IC50 183 meas. best 9.19
Kd 11 meas. best 8.15
Ki 8 meas. best 8.15
EC50 7 meas. best 7.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DNA gyrase
CHEMBL3038482
IC50 9.19 7.6023 0.7 13
Unchecked
CHEMBL612545
IC50 8.66 6.0288 2.2 67
DNA gyrase
CHEMBL2094139
IC50 8.35 7.0246 4.5 13
DNA gyrase subunit B
CHEMBL1826
Kd 8.15 7.85 7.0 2
DNA gyrase subunit B
CHEMBL1826
Ki 8.15 8.15 7.0 1
DNA gyrase
CHEMBL3038482
Ki 8.0 8.0 10.0 1
Unchecked
CHEMBL612545
Ki 7.85 6.3433 14.0 3
DNA gyrase subunit A/DNA gyrase subunit B
CHEMBL3430898
IC50 7.82 7.393 15.0 10
Unchecked
CHEMBL612545
Kd 7.72 7.6067 19.0 3
DNA gyrase subunit B
CHEMBL1075021
IC50 7.43 7.43 37.0 1
DNA gyrase subunit B
CHEMBL1921666
IC50 7.4 7.27 40.0 4
DNA gyrase subunit B
CHEMBL3085613
IC50 7.34 6.84 46.0 6
DNA gyrase subunit B
CHEMBL6059
IC50 7.34 7.34 46.0 1
SH-SY5Y
CHEMBL614910
EC50 7.32 7.32 48.4 1
Staphylococcus aureus
CHEMBL352
IC50 6.9 6.9 125.0 1
DNA gyrase subunit B
CHEMBL1826
IC50 6.81 6.764 154.0 5
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.98 5.98 1050.0 1
ParE
CHEMBL1075022
IC50 5.69 5.69 2030.0 1
Microtubule-associated proteins 1A/1B light chain 3A
CHEMBL4879518
Kd 5.12 5.12 7500.0 1
DNA topoisomerase 4 subunit B
CHEMBL2150841
IC50 5.1 5.1 7900.0 1
Microtubule-associated proteins 1A/1B light chain 3A
CHEMBL4879518
Ki 5.06 5.06 8800.0 1
Albumin
CHEMBL3253
Kd 4.92 4.92 12000.0 1
Topoisomerase IV
CHEMBL3038508
IC50 4.88 4.6171 13265.0 7
Nonstructural protein 3
CHEMBL4523954
IC50 4.85 4.85 14200.0 1
Microtubule-associated proteins 1A/1B light chain 3B
CHEMBL4879514
Kd 4.76 4.76 17400.0 1
Microtubule-associated proteins 1A/1B light chain 3B
CHEMBL4879514
Ki 4.71 4.71 19300.0 1
DNA polymerase theta
CHEMBL6025
IC50 4.62 4.502 24000.0 5
MDA-MB-436
CHEMBL4296465
IC50 4.61 4.61 24300.0 1
Nonstructural protein 3
CHEMBL4523954
EC50 4.61 4.61 24800.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 4.6 4.355 25000.0 4
Microtubule-associated proteins 1A/1B light chain 3A
CHEMBL4879518
IC50 4.37 4.37 42900.0 1
Zika virus
CHEMBL4296612
EC50 4.21 4.21 62200.0 1
Heat shock protein HSP90
CHEMBL2095165
IC50 4.08 4.08 82430.0 1
TERT-RPE1
CHEMBL615013
IC50 4.07 4.04 86000.0 2
Unchecked
CHEMBL612545
EC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL - - Mus musculus
t1/2 - - Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DNA gyrase IC50 = 0.65 nM 9.19 Inhibition of Staphylococcus aureus DNA gyrase supercoiling incubated for 30 min... 36877255
Unchecked IC50 = 2.17 nM 8.66 Inhibition of Acinetobacter baumannii DNA gyrase supercoiling incubated for 30 m... 36877255
Unchecked IC50 = 3.0 nM 8.52 Inhibition of Escherichia coli DNA gyrase B ATPase activity 20045642
Unchecked IC50 = 3.0 nM 8.52 Inhibition of DNA gyrase B 22444877
DNA gyrase IC50 = 4.52 nM 8.35 Inhibition of Escherichia coli DNA gyrase 35694689
DNA gyrase subunit B Kd = 7.0 nM 8.15 Binding affinity to Escherichia coli H560 DNA gyrase B 27569197
DNA gyrase subunit B Ki = 7.0 nM 8.15 Inhibition of Escherichia coli H560 DNA gyrase B ATPase activity after 30 mins b... 27569197
Unchecked IC50 = 8.0 nM 8.1 Displacement of novobiocin-TRX from Francisella tularensis Schu S4 gyraseB by fl... 21871799
DNA gyrase Ki = 10.0 nM 8.0 Inhibition of Staphylococcus aureus DNA gyrase 18690678
DNA gyrase IC50 = 10.0 nM 8.0 Inhibition of Staphylococcus aureus DNA gyrase using relaxed pBR322 DNA as subst... 26098163
DNA gyrase IC50 = 10.0 nM 8.0 Inhibition of Staphylococcus aureus DNA gyrase assessed as supercoiling of relax... 27100032
Unchecked IC50 = 10.0 nM 8.0 Inhibition of Staphylococcus aureus DNA gyrase supercoiling activity using relax... 28246042
Unchecked IC50 = 10.0 nM 8.0 Inhibition of Staphylococcus aureus DNA gyrase using relaxed pBR322 DNA as subst... 27689732
Unchecked Ki = 14.0 nM 7.85 Inhibition of Escherichia coli DNA gyrase 18690678
DNA gyrase subunit A/DNA gyrase subunit B IC50 = 15.0 nM 7.82 Inhibition of Mycobacterium tuberculosis DNA gyrase-mediated relaxed pBR322 DNA ... 25221657
Unchecked IC50 = 15.0 nM 7.82 Inhibition of Staphylococcus aureus Gyrase B using linear pBR322 DNA as substrat... 31901744
Unchecked IC50 = 15.0 nM 7.82 Inhibition of Escherichia coli DNA gyrase B using relaxed pNO1 as substrate afte... 22444877
Unchecked Kd = 19.0 nM 7.72 Binding affinity to Escherichia coli DNA gyrase B 27100032
DNA gyrase subunit A/DNA gyrase subunit B IC50 = 20.0 nM 7.7 Inhibition of Mycobacterium tuberculosis DNA gyrase ATPase activity 30122228
DNA gyrase IC50 = 23.0 nM 7.64 Inhibition of Escherichia coli DNA gyrase ATPase activity 27143131

Literature References

PubMed DOI Target Context # Activities
19258280 10.1128/aac.01024-08 Pseudomonas aeruginosa 31
17606680 10.1128/aac.01481-06 Escherichia coli 27
30034678 10.1039/C7MD00012J Escherichia coli 24
20211889 10.1128/aac.01677-09 Escherichia coli 20
17116675 10.1128/aac.00596-06 Staphylococcus aureus 14
24098982 10.1021/jm401208b NON-PROTEIN TARGET 13
28406299 10.1021/acs.jmedchem.6b01834 Unchecked 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
38375763 10.1021/acs.jmedchem.3c02096 MDA-MB-231 11
19564371 10.1128/aac.00550-09 Mycobacterium tuberculosis 10
17979263 10.1021/jm0707774 MCF7 10
18936189 10.1128/aac.00921-08 Escherichia coli 10
18070975 10.1128/aac.01095-07 Mycobacterium leprae 8
23084277 10.1016/j.bmcl.2012.09.071 Staphylococcus aureus 8
17876001 10.1128/aac.00708-07 Staphylococcus aureus 8
19564371 10.1128/aac.00550-09 Mycobacterium tuberculosis variant bovis BCG 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20876376 10.1128/aac.00719-10 Escherichia coli 8
17638702 10.1128/aac.00072-07 Enterobacter cloacae 8
27100032 10.1016/j.ejmech.2016.03.079 Unchecked 8

Data from ChEMBL 36 via Core Engine