(1R,14S,15R)-25-methyl-4,25-diazahexacyclo[13.7.3.0^{1,14}.0^{3,12}.0^{5,10}.0^{17,22}]pentacosa-3(12),4,6,8,10,17,19,21-octaene-14,20-diol

ID: ALA1270282

Chembl Id: CHEMBL1270282

Cas Number: 1256921-89-7

PubChem CID: 52942137

Max Phase: Preclinical

Molecular Formula: C24H24N2O2

Molecular Weight: 372.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@]23Cc4nc5ccccc5cc4C[C@@]2(O)[C@H]1Cc1ccc(O)cc13

Standard InChI:  InChI=1S/C24H24N2O2/c1-26-9-8-23-14-21-17(10-16-4-2-3-5-20(16)25-21)13-24(23,28)22(26)11-15-6-7-18(27)12-19(15)23/h2-7,10,12,22,27-28H,8-9,11,13-14H2,1H3/t22-,23-,24-/m1/s1

Standard InChI Key:  NFXFNBIPWUYEIM-WXFUMESZSA-N

Alternative Forms

1. Parent:

   

   ALA1270282

   (1R,14S,15R)-25-methyl-4,25-diazahexacyclo[13.7.3.01,14.03,12.05,10.017,22]pentacosa-3,5,7,9,11,17(22),18,20-octaene-14,20-diol

2. Alternative Forms:

   

   ALA1270282

   ---

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

Calculated Properties

Molecular Weight: 372.47

Molecular Weight (Monoisotopic): 372.1838

AlogP: 2.97

#Rotatable Bonds: ┄

Polar Surface Area: 56.59

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.20

CX Basic pKa: 8.05

CX LogP: 3.21

CX LogD: 2.47

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: 0.89

References

1. Nagase H, Nemoto T, Matsubara A, Saito M, Yamamoto N, Osa Y, Hirayama S, Nakajima M, Nakao K, Mochizuki H, Fujii H..  (2010)  Design and synthesis of KNT-127, a δ-opioid receptor agonist effective by systemic administration.,  20  (21): [PMID:20850307] [10.1016/j.bmcl.2010.08.083]

2. Ida Y, Matsubara A, Nemoto T, Saito M, Hirayama S, Fujii H, Nagase H..  (2012)  Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands.,  20  (19): [PMID:22967810] [10.1016/j.bmc.2012.08.004]

3. Kutsumura N, Koyama Y, Nagumo Y, Nakajima R, Miyata Y, Yamamoto N, Saitoh T, Yoshida N, Iwata S, Nagase H..  (2017)  Antitrichomonal activity of δ opioid receptor antagonists, 7-benzylidenenaltrexone derivatives.,  25  (16): [PMID:28662966] [10.1016/j.bmc.2017.06.026]

4. Fujii H, Uchida Y, Shibasaki M, Nishida M, Yoshioka T, Kobayashi R, Honjo A, Itoh K, Yamada D, Hirayama S, Saitoh A..  (2020)  Discovery of δ opioid receptor full agonists lacking a basic nitrogen atom and their antidepressant-like effects.,  30  (12): [PMID:32299730] [10.1016/j.bmcl.2020.127176]

5. Iio K, Kutsumura N, Nagumo Y, Saitoh T, Tokuda A, Hashimoto K, Yamamoto N, Kise R, Inoue A, Mizoguchi H, Nagase H..  (2022)  Synthesis of unnatural morphinan compounds to induce itch-like behaviors in mice: Towards the development of MRGPRX2 selective ligands.,  56  [PMID:34861349] [10.1016/j.bmcl.2021.128485]

Source

Source(1):

• Scientific Literature