omega-Hydroxyfentanyl

ID: ALA4526998

Cas Number: 83708-11-6

PubChem CID: 71748858

Max Phase: Preclinical

Molecular Formula: C22H28N2O2

Molecular Weight: 352.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCO)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1

Standard InChI:  InChI=1S/C22H28N2O2/c25-18-14-22(26)24(20-9-5-2-6-10-20)21-12-16-23(17-13-21)15-11-19-7-3-1-4-8-19/h1-10,21,25H,11-18H2

Standard InChI Key:  BXGSQUNMZMHPKS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.4018  -14.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4007  -15.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1129  -15.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225  -15.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8197  -14.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111  -14.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5300  -14.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5269  -13.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372  -12.9794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9457  -13.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6539  -12.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6550  -12.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418  -11.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275  -12.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3669  -11.7460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0787  -12.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3669  -10.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0787  -10.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6551  -10.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0788   -9.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0754  -12.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7823  -13.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4951  -12.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4925  -12.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7809  -11.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7865   -9.2821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 16 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 16  1  0
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526998

   3-Hydroxy-N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 352.48

Molecular Weight (Monoisotopic): 352.2151

AlogP: 3.11

#Rotatable Bonds: 7

Polar Surface Area: 43.78

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.77

CX LogP: 2.53

CX LogD: 1.15

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.83

Np Likeness Score: -0.93

References

1. Lipiński PFJ, Szűcs E, Jarończyk M, Kosson P, Benyhe S, Misicka A, Dobrowolski JC, Sadlej J..  (2019)  Affinity of fentanyl and its derivatives for the σ₁-receptor.,  10  (7): [PMID:31391893] [10.1039/C9MD00222G]

Source

Source(1):

• Scientific Literature