(1R,9R,10S)-17-(cyclopropylmethyl)-4,10-dihydroxy-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6-trien-13-one

ID: ALA1797689

Chembl Id: CHEMBL1797689

Cas Number: 26989-39-9

PubChem CID: 5493351

Max Phase: Preclinical

Molecular Formula: C20H25NO3

Molecular Weight: 327.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC[C@@]2(O)[C@H]3Cc4ccc(O)cc4[C@@]2(CCN3CC2CC2)C1

Standard InChI:  InChI=1S/C20H25NO3/c22-15-4-3-14-9-18-20(24)6-5-16(23)11-19(20,17(14)10-15)7-8-21(18)12-13-1-2-13/h3-4,10,13,18,22,24H,1-2,5-9,11-12H2/t18-,19-,20-/m1/s1

Standard InChI Key:  JKSUUZMNWGEVRC-VAMGGRTRSA-N

Alternative Forms

1. Parent:

   

   ALA1797689

   Morphinan-6-one, 17-(cyclopropylmethyl)-3,14-dihydroxy-

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: 327.42

Molecular Weight (Monoisotopic): 327.1834

AlogP: 2.15

#Rotatable Bonds: 2

Polar Surface Area: 60.77

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.84

CX Basic pKa: 9.04

CX LogP: 1.50

CX LogD: 0.21

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.87

Np Likeness Score: 1.48

References

1. Yamamoto N, Fujii H, Nemoto T, Nakajima R, Momen S, Izumimoto N, Hasebe K, Mochizuki H, Nagase H..  (2011)  Synthesis of new opioid derivatives with a propellane skeleton and their pharmacology: part 1.,  21  (13): [PMID:21641798] [10.1016/j.bmcl.2011.04.147]

2. Ishikawa K, Mochizuki Y, Hirayama S, Nemoto T, Nagai K, Itoh K, Fujii H..  (2016)  Synthesis and evaluation of novel opioid ligands with a C-homomorphinan skeleton.,  24  (10): [PMID:27079125] [10.1016/j.bmc.2016.03.040]

Source

Source(1):

• Scientific Literature