2-Methyl-1,2-di-pyridin-3-yl-propan-1-ol

ID: ALA933

Cas Number: 17159-42-1

PubChem CID: 161210

Max Phase: Preclinical

Molecular Formula: C14H16N2O

Molecular Weight: 228.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Metyrapol | Metyrapol|17159-42-1|2-methyl-1,2-dipyridin-3-ylpropan-1-ol|SU-5236|2-methyl-1,2-di(pyridin-3-yl)propan-1-ol|CHEMBL933|2-Methyl-1,2-bis(3-pyridyl)-1-propanol|METYRAPOL (MPOL)|DTXSID10938007|CHEBI:172467|BDBM50028160|AKOS030241945|2-Methyl-1,2-di-pyridin-3-yl-propan-1-ol|A904438

Canonical SMILES:  CC(C)(c1cccnc1)C(O)c1cccnc1

Standard InChI:  InChI=1S/C14H16N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10,13,17H,1-2H3

Standard InChI Key:  DDFNHFXLQJLFSX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -0.3333    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -0.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -0.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    0.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000    0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  8  2  0
  6 11  1  0
  7  2  1  0
  8  3  1  0
  9  1  1  0
 10  1  1  0
 11  4  2  0
 12  3  2  0
 13 17  1  0
 14 16  2  0
 15  4  1  0
 16 12  1  0
 17 15  2  0
 13  6  2  0
  5 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA933

   METYRAPOL

Molecule Features

Natural Product: Yes

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: 228.29

Molecular Weight (Monoisotopic): 228.1263

AlogP: 2.49

#Rotatable Bonds: 3

Polar Surface Area: 46.01

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.65

CX Basic pKa: 5.40

CX LogP: 1.59

CX LogD: 1.58

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.88

Np Likeness Score: -0.40

References

1. Hays SJ, Tobes MC, Gildersleeve DL, Wieland DM, Beierwaltes WH..  (1984)  Structure-activity relationship study of the inhibition of adrenal cortical 11 beta-hydroxylase by new metyrapone analogues.,  27  (1): [PMID:6606707] [10.1021/jm00367a004]

2. Zolle IM, Berger ML, Hammerschmidt F, Hahner S, Schirbel A, Peric-Simov B..  (2008)  New selective inhibitors of steroid 11beta-hydroxylation in the adrenal cortex. Synthesis and structure-activity relationship of potent etomidate analogues.,  51  (7): [PMID:18348518] [10.1021/jm800012w]

3. Atucha E, Hammerschmidt F, Zolle I, Sieghart W, Berger ML..  (2009)  Structure-activity relationship of etomidate derivatives at the GABA(A) receptor: Comparison with binding to 11beta-hydroxylase.,  19  (15): [PMID:19497738] [10.1016/j.bmcl.2009.05.065]

4. Napoli JL, Counsell RE..  (1977)  New inhibitors of steroid 11beta-hydroxylase. Structure--activity relationship studies of metyrapone-like compounds.,  20  (6): [PMID:874952] [10.1021/jm00216a005]

Source

Source(1):

• Scientific Literature