ID: ALA409225

Max Phase: Preclinical

Molecular Formula: C25H29N5O5

Molecular Weight: 479.54

Molecule Type: Small molecule

Representations

Synonyms (1): SB-0304
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@H](C(=O)N[C@H]1Cc2ccccc2CN(CC(N)=O)C1=O)N1Cc2cc(O)ccc2C[C@H](N)C1=O

Standard InChI:  InChI=1S/C25H29N5O5/c1-14(30-12-18-8-19(31)7-6-16(18)9-20(26)24(30)34)23(33)28-21-10-15-4-2-3-5-17(15)11-29(25(21)35)13-22(27)32/h2-8,14,20-21,31H,9-13,26H2,1H3,(H2,27,32)(H,28,33)/t14-,20+,21+/m1/s1

Standard InChI Key:  ACFTTXWQZSBVGL-OREJSRFESA-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: 479.54

Molecular Weight (Monoisotopic): 479.2169

AlogP: -0.45

#Rotatable Bonds: 5

Polar Surface Area: 159.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.38

CX Basic pKa: 7.70

CX LogP: -0.78

CX LogD: -1.09

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.45

Np Likeness Score: -0.19

References

1. Ballet S, Misicka A, Kosson P, Lemieux C, Chung NN, Schiller PW, Lipkowski AW, Tourwé D..  (2008)  Blood-brain barrier penetration by two dermorphin tetrapeptide analogues: role of lipophilicity vs structural flexibility.,  51  (8): [PMID:18370374] [10.1021/jm701404s]

2. Vandormael B, Fourla DD, Gramowski-Voss A, Kosson P, Weiss DG, Schröder OH, Lipkowski A, Georgoussi Z, Tourwé D..  (2011)  Superpotent [Dmt¹] dermorphin tetrapeptides containing the 4-aminotetrahydro-2-benzazepin-3-one scaffold with mixed μ/δ opioid receptor agonistic properties.,  54  (22): [PMID:21978284] [10.1021/jm200894e]

Source

Source(1):

• Scientific Literature