11-Phenylakuammine

ID: ALA5284877

Max Phase: Preclinical

Molecular Formula: C28H30N2O4

Molecular Weight: 458.56

Names and Identifiers

Canonical SMILES:  C/C=C1/CN2CC[C@@]34c5cc(O)c(-c6ccccc6)cc5N(C)[C@]35OC[C@@]4(C(=O)OC)[C@H]1C[C@H]25

Standard InChI:  InChI=1S/C28H30N2O4/c1-4-17-15-30-11-10-27-21-13-23(31)19(18-8-6-5-7-9-18)12-22(21)29(2)28(27)24(30)14-20(17)26(27,16-34-28)25(32)33-3/h4-9,12-13,20,24,31H,10-11,14-16H2,1-3H3/b17-4-/t20-,24-,26-,27-,28+/m0/s1

Standard InChI Key:  CTSCUOIRSHSOLW-MZMPVIMOSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5284877

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 458.56

Molecular Weight (Monoisotopic): 458.2206

AlogP: 3.69

#Rotatable Bonds: 2

Polar Surface Area: 62.24

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.81

CX Basic pKa: 7.07

CX LogP: 4.20

CX LogD: 4.03

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.55

Np Likeness Score: 1.94

References

1. Hennessy MR, Gutridge AM, French AR, Rhoda ES, Meqbil YJ, Gill M, Kashyap Y, Appourchaux K, Paul B, Wang ZJ, van Rijn RM, Riley AP..  (2023)  Modified Akuamma Alkaloids with Increased Potency at the Mu-opioid Receptor.,  66  (5): [PMID:36827198] [10.1021/acs.jmedchem.2c01707]

Source

Source(1):

• Scientific Literature