2-((S)-2-guanidino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

ID: ALA3038178

Chembl Id: CHEMBL3038178

PubChem CID: 73352752

Max Phase: Preclinical

Molecular Formula: C22H26N4O4

Molecular Weight: 410.47

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](NC(=N)N)C(=O)N1Cc2ccccc2C[C@H]1C(=O)O

Standard InChI:  InChI=1S/C22H26N4O4/c1-12-7-16(27)8-13(2)17(12)10-18(25-22(23)24)20(28)26-11-15-6-4-3-5-14(15)9-19(26)21(29)30/h3-8,18-19,27H,9-11H2,1-2H3,(H,29,30)(H4,23,24,25)/t18-,19-/m0/s1

Standard InChI Key:  UPXNEROFENYEAW-OALUTQOASA-N

Associated Targets(non-human)

OPRK1 mu/kappa opioid receptor (15 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprd1 Delta opioid receptor (3127 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Kappa opioid receptor (4577 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprd1 Delta opioid receptor (3911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprm1 Mu opioid receptor (6060 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 410.47Molecular Weight (Monoisotopic): 410.1954AlogP: 1.44#Rotatable Bonds: 5
Polar Surface Area: 139.74Molecular Species: ZWITTERIONHBA: 4HBD: 5
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 6#RO5 Violations (Lipinski): 1
CX Acidic pKa: 3.63CX Basic pKa: 11.59CX LogP: 0.92CX LogD: 0.91
Aromatic Rings: 2Heavy Atoms: 30QED Weighted: 0.37Np Likeness Score: 0.00

References

1. Weltrowska G, Nguyen TM, Chung NN, Wilkes BC, Schiller PW..  (2013)  N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.,  23  (18): [PMID:23932788] [10.1016/j.bmcl.2013.07.036]

Source