fasidotril   Click here for help

GtoPdb Ligand ID: 6501

Synonyms: aladotril | BP-1137
Compound class: Synthetic organic
Comment: Prodrug of fasidotrilat, a combined ACE and NEP inhibitor. There is some ambiguity online as to the exact stereochemistry of fasidotril. Our structure is drawn from the INN document and matches that represented in the PubChem and ChEMBL entries linked to above.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 12
Topological polar surface area 116.23
Molecular weight 443.14
XLogP 3.13
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC(=O)SCC(C(=O)NC(C(=O)OCc1ccccc1)C)Cc1ccc2c(c1)OCO2
Isomeric SMILES CC(=O)SC[C@H](C(=O)N[C@H](C(=O)OCc1ccccc1)C)Cc1ccc2c(c1)OCO2
InChI InChI=1S/C23H25NO6S/c1-15(23(27)28-12-17-6-4-3-5-7-17)24-22(26)19(13-31-16(2)25)10-18-8-9-20-21(11-18)30-14-29-20/h3-9,11,15,19H,10,12-14H2,1-2H3,(H,24,26)/t15-,19+/m0/s1
InChI Key KKBIUAUSZKGNOA-HNAYVOBHSA-N
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form fasidotrilat
IUPAC Name Click here for help
phenylmethyl (2S)-2-[[(2S)-2-(acetylsulfanylmethyl)-3-(1,3-benzodioxol-5-yl)propanoyl]amino]propanoate
International Nonproprietary Names Click here for help
INN number INN
7286 fasidotril
Synonyms Click here for help
aladotril | BP-1137
Database Links Click here for help
CAS Registry No. 135038-57-2 (source: PubChem)
ChEMBL Ligand CHEMBL325695
GtoPdb PubChem SID 178103115
PubChem CID 5311337
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Search UniChem for chemical match using the InChIKey KKBIUAUSZKGNOA-HNAYVOBHSA-N
Search UniChem for chemicals with the same backbone KKBIUAUSZKGNOA