Details of the Drug

General Information of Drug (ID: DM86LFB)

Drug Name

Thiorphan

Synonyms

(S)-THIORPHAN; (2-MERCAPTOMETHYL-3-PHENYL-PROPIONYL)-GLYCINE; CHEMBL298827; 95909-00-5; 1zdp; AC1N9ZZO; Lopac-T-6031; SCHEMBL49662; GTPL5278; Glycine, N-[(2S)-2-(mercaptomethyl)-1-oxo-3-phenylpropyl]-; ZINC3872336; BDBM50024102; DB08626; NCGC00016033-01; NCGC00016933-01; CAS-76721-89-6; N-[(2S)-2-benzyl-3-sulfanylpropanoyl]glycine; 2-[(2S)-2-benzyl-3-sulfanylpropanamido]acetic acid; (S) (2-Mercaptomethyl-3-phenyl-propionylamino)-acetic acid; 2-[[(2S)-2-benzyl-3-sulfanylpropanoyl]amino]acetic acid; UNII-B79L7B5X3Z component LJJ

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

253.32

Logarithm of the Partition Coefficient (xlogp)

1.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 11.1177 micromolar/kg/day [2]

Chemical Identifiers

Formula: C12H15NO3S
IUPAC Name: 2-[(2-benzyl-3-sulfanylpropanoyl)amino]acetic acid
Canonical SMILES: C1=CC=C(C=C1)CC(CS)C(=O)NCC(=O)O
InChI: InChI=1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)
InChIKey: LJJKNPQAGWVLDQ-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3132
ChEBI ID: CHEBI:9568
CAS Number: 76721-89-6
UNII: XJ8Z52GK3X
DrugBank ID: DB08626
TTD ID: D0PB5Q

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Neutral endopeptidase (MME)	TT5TKPM	NEP_HUMAN	Inhibitor	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Eukaryotic translation initiation factor 4E-binding protein 1 (EIF4EBP1)	OTHBQVD5	4EBP1_HUMAN	Post-Translational Modifications	[4]
Insulin-like growth factor-binding protein 5 (IGFBP5)	OTRE5V0C	IBP5_HUMAN	Gene/Protein Processing	[5]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[4]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Post-Translational Modifications	[4]
Neprilysin (MME)	OT5Q39P8	NEP_HUMAN	Gene/Protein Processing	[5]
RAC-alpha serine/threonine-protein kinase (AKT1)	OT8H2YY7	AKT1_HUMAN	Post-Translational Modifications	[5]
Ribosomal protein S6 kinase beta-1 (RPS6KB1)	OTAELNGX	KS6B1_HUMAN	Post-Translational Modifications	[4]
Serine/threonine-protein kinase mTOR (MTOR)	OTHH8KU7	MTOR_HUMAN	Post-Translational Modifications	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5278).
2	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
3	Thiorphan enhances bradykinin-induced vascular relaxation in hypoxic/hyperkalaemic porcine coronary artery. J Pharm Pharmacol. 2003 Mar;55(3):339-45.
4	Neutral endopeptidase (NEP) inhibitors - thiorphan, sialorphin, and its derivatives exert anti-proliferative activity towards colorectal cancer cells in vitro. Chem Biol Interact. 2019 Jul 1;307:105-115. doi: 10.1016/j.cbi.2019.04.033. Epub 2019 May 1.
5	Neprilysin participates in skeletal muscle regeneration and is accumulated in abnormal muscle fibres of inclusion body myositis. J Neurochem. 2006 Feb;96(3):777-89.