7-hydroxy efavirenz

ID: ALA3526537

Cas Number: 252343-24-1

PubChem CID: 40621976

Max Phase: Preclinical

Molecular Formula: C14H9ClF3NO3

Molecular Weight: 331.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2cc(O)c(Cl)cc2[C@@](C#CC2CC2)(C(F)(F)F)O1

Standard InChI:  InChI=1S/C14H9ClF3NO3/c15-9-5-8-10(6-11(9)20)19-12(21)22-13(8,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)/t13-/m0/s1

Standard InChI Key:  GZMDZAYFVCXHFM-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.0988   -5.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6861   -5.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3972   -4.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8376   -4.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5033   -5.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -4.8660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1319   -3.6278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4137   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2816   -6.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8648   -7.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6791   -5.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590   -7.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8689   -8.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5599   -3.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7038   -3.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0947   -6.6861    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3287   -5.9762    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9160   -6.6861    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9692   -4.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898   -3.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2510   -5.2127    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2918   -3.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  6  1  0
  1  5  1  6
  6  1  1  0
  7  4  1  0
  8  3  1  0
  9  2  3  0
 10  9  1  0
 11  3  2  0
 12 10  1  0
 13 10  1  0
 14  4  2  0
 15  8  2  0
 16  5  1  0
 17  5  1  0
 18  5  1  0
 19 11  1  0
 20 19  2  0
 21 19  1  0
  8  7  1  0
 20 15  1  0
 12 13  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3526537

   7-Hydroxyefavirenz

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: 331.68

Molecular Weight (Monoisotopic): 331.0223

AlogP: 3.78

#Rotatable Bonds: ┄

Polar Surface Area: 58.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.54

CX Basic pKa: ┄

CX LogP: 4.15

CX LogD: 3.92

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.71

Np Likeness Score: 0.56

References

1. Avery LB, VanAusdall JL, Hendrix CW, Bumpus NN..  (2013)  Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.,  41  (2): [PMID:23166317] [10.1124/dmd.112.049601]

Source

Source(1):

• Scientific Literature