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CA-074 methyl ester

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Identification

Generic Name
CA-074 methyl ester
DrugBank Accession Number
DB07223
Background

CA-074 methyl ester (CA-074Me) is a cell-permeable cathepsin B inhibitor. It is converted by cellular esterases to CA-074.1,2

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 397.4659
Monoisotopic: 397.221285739
Chemical Formula
C19H31N3O6
Synonyms
  • (S)-methyl 1-((2S,3S)-3-methyl-2-((2S,3S)-3-(propylcarbamoyl)oxirane-2-carboxamido)pentanoyl)pyrrolidine-2-carboxylate
  • CA 074 Me ester
  • CA 074 methyl ester
  • L-Proline, 1-[N-[[3-[(propylamino)carbonyl]oxiranyl]carbonyl]-L-isoleucyl]-, methyl ester, (2S-trans)-
  • L-Proline, N-[[(2S,3S)-3-[(propylamino)carbonyl]oxiranyl]carbonyl]-L-isoleucyl-, methyl ester
  • Methyl (2S)-1-[(2S,3S)-3-methyl-2-[[(2S,3S)-3-(propylcarbamoyl)oxirane-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carboxylate
  • Methyl N-({(2s,3s)-3-[(propylamino)carbonyl]oxiran-2-Yl}carbonyl)-L-isoleucyl-L-prolinate
External IDs
  • CA 074Me
  • CA-074 Me
  • CA-074Me
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCathepsin BNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Peptides
Alternative Parents
Isoleucine and derivatives / Alpha amino acid esters / Proline and derivatives / N-acyl-alpha amino acids / Alpha amino acid amides / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Oxirane carboxylic acids and derivatives / Methyl esters / Tertiary carboxylic acid amides
show 10 more
Substituents
Aliphatic heteromonocyclic compound / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid ester / Dialkyl ether
show 24 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
147859-80-1
InChI Key
XGWSRLSPWIEMLQ-YTFOTSKYSA-N
InChI
InChI=1S/C19H31N3O6/c1-5-9-20-16(23)14-15(28-14)17(24)21-13(11(3)6-2)18(25)22-10-7-8-12(22)19(26)27-4/h11-15H,5-10H2,1-4H3,(H,20,23)(H,21,24)/t11-,12-,13-,14-,15-/m0/s1
IUPAC Name
methyl (2S)-1-[(2S,3S)-3-methyl-2-{[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]formamido}pentanoyl]pyrrolidine-2-carboxylate
SMILES
[H][C@](C)(CC)[C@]([H])(NC(=O)[C@@]1([H])O[C@]1([H])C(=O)NCCC)C(=O)N1CCC[C@@]1([H])C(=O)OC

References

General References
  1. Yoon MC, Christy MP, Phan VV, Gerwick WH, Hook G, O'Donoghue AJ, Hook V: Molecular Features of CA-074 pH-Dependent Inhibition of Cathepsin B. Biochemistry. 2022 Feb 15;61(4):228-238. doi: 10.1021/acs.biochem.1c00684. Epub 2022 Feb 4. [Article]
  2. Jane DT, Morvay LC, Allen F, Sloane BF, Dufresne MJ: Selective inhibition of cathepsin B with cell-permeable CA074Me negatively affects L6 rat myoblast differentiation. Biochem Cell Biol. 2002;80(4):457-65. doi: 10.1139/o02-134. [Article]
PubChem Compound
6610318
PubChem Substance
99443694
ChemSpider
5042571
BindingDB
16503
ChEMBL
CHEMBL262103
ZINC
ZINC000004899858
PDBe Ligand
74M
PDB Entries
2dc9

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.9 mg/mLALOGPS
logP0.76ALOGPS
logP0.31Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.2Chemaxon
pKa (Strongest Basic)-3.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area117.34 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity99.34 m3·mol-1Chemaxon
Polarizability41.92 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8421
Blood Brain Barrier-0.7765
Caco-2 permeable-0.6654
P-glycoprotein substrateSubstrate0.7129
P-glycoprotein inhibitor IInhibitor0.5386
P-glycoprotein inhibitor IIInhibitor0.506
Renal organic cation transporterNon-inhibitor0.9269
CYP450 2C9 substrateNon-substrate0.9096
CYP450 2D6 substrateNon-substrate0.8197
CYP450 3A4 substrateSubstrate0.5243
CYP450 1A2 substrateNon-inhibitor0.7625
CYP450 2C9 inhibitorNon-inhibitor0.775
CYP450 2D6 inhibitorNon-inhibitor0.8701
CYP450 2C19 inhibitorNon-inhibitor0.7213
CYP450 3A4 inhibitorInhibitor0.5831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7654
Ames testNon AMES toxic0.6917
CarcinogenicityNon-carcinogens0.8652
BiodegradationNot ready biodegradable0.8975
Rat acute toxicity2.4300 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9853
hERG inhibition (predictor II)Non-inhibitor0.7976
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1219000000-8bd6c5161472ad382789
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ta-2719000000-b50dab23412673e9725a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0532-9747000000-f0ea66e0224c73404b0e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fs-7967000000-80fc8ed7fec070a5ce79
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pi4-9432000000-a7f3018685fe556a184d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-9701000000-2320f4ca301d5c991de0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-190.21602
predicted
DeepCCS 1.0 (2019)
[M+H]+192.04091
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.64673
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cathepsin B
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thiol protease which is believed to participate in intracellular degradation and turnover of proteins (PubMed:12220505). Cleaves matrix extracellular phosphoglycoprotein MEPE (PubMed:12220505). Involved in the solubilization of cross-linked TG/thyroglobulin in the thyroid follicle lumen (By similarity). Has also been implicated in tumor invasion and metastasis (PubMed:3972105)
Specific Function
collagen binding
Gene Name
CTSB
Uniprot ID
P07858
Uniprot Name
Cathepsin B
Molecular Weight
37821.35 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:19 / Updated at March 14, 2023 09:13