ID: ALA119590

Max Phase: Preclinical

Molecular Formula: C39H45N5O4

Molecular Weight: 647.82

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N1Cc2ccccc2CC1CN[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C39H45N5O4/c1-25-17-32(45)18-26(2)33(25)22-34(40)39(48)44-24-30-16-10-9-15-29(30)21-31(44)23-42-36(20-28-13-7-4-8-14-28)38(47)43-35(37(41)46)19-27-11-5-3-6-12-27/h3-18,31,34-36,42,45H,19-24,40H2,1-2H3,(H2,41,46)(H,43,47)/t31?,34-,35-,36-/m0/s1

Standard InChI Key:  MZZBNDGZTPEYGP-QHMGJUIVSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 647.82

Molecular Weight (Monoisotopic): 647.3472

AlogP: 3.25

#Rotatable Bonds: 13

Polar Surface Area: 150.78

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.75

CX Basic pKa: 8.04

CX LogP: 4.77

CX LogD: 3.57

Aromatic Rings: 4

Heavy Atoms: 48

QED Weighted: 0.15

Np Likeness Score: 0.06

References

1. Schiller PW, Fundytus ME, Merovitz L, Weltrowska G, Nguyen TM, Lemieux C, Chung NN, Coderre TJ..  (1999)  The opioid mu agonist/delta antagonist DIPP-NH(2)[Psi] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats.,  42  (18): [PMID:10479285] [10.1021/jm980724+]

2. 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

Source(1):

• Scientific Literature