o-Methylisoprenaline

ID: ALA2074647

Cas Number: 1212-03-9

PubChem CID: 68951

Max Phase: Phase

Molecular Formula: C12H19NO3

Molecular Weight: 225.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(O)CNC(C)C)ccc1O

Standard InChI:  InChI=1S/C12H19NO3/c1-8(2)13-7-11(15)9-4-5-10(14)12(6-9)16-3/h4-6,8,11,13-15H,7H2,1-3H3

Standard InChI Key:  XXCCGRRUBBGZRE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    5.5982   -3.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8837   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8837   -5.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5982   -5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3127   -5.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3127   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5982   -3.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3127   -2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8837   -2.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3127   -1.9152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0272   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0272   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7416   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5982   -6.4527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1692   -5.6277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4548   -5.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  7  1  0
  7  8  1  0
  7  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  4 14  1  0
  3 15  1  0
 15 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074647

   METIPRENALINE

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: 225.29

Molecular Weight (Monoisotopic): 225.1365

AlogP: 1.43

#Rotatable Bonds: 5

Polar Surface Area: 61.72

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: 9.36

CX LogP: 0.74

CX LogD: -0.90

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.71

Np Likeness Score: 0.37

References

1. Martel F, Vetter T, Russ H, Gründemann D, Azevedo I, Koepsell H, Schömig E..  (1996)  Transport of small organic cations in the rat liver. The role of the organic cation transporter OCT1.,  354  (1): [PMID:8878062] [10.1007/bf00171063]

2. Gründemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H..  (1994)  Drug excretion mediated by a new prototype of polyspecific transporter.,  372  (1): [PMID:7990927] [10.1038/372549a0]

3. Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H..  (1997)  Cloning and characterization of two human polyspecific organic cation transporters.,  16  (1): [PMID:9260930] [10.1089/dna.1997.16.871]

4. Gründemann D, Köster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermüller N, Schömig E..  (1998)  Transport of monoamine transmitters by the organic cation transporter type 2, OCT2.,  273  (1): [PMID:9812985] [10.1074/jbc.273.47.30915]

5. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H..  (2001)  Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1.,  281  (1): [PMID:11502595] [10.1152/ajprenal.2001.281.3.f454]

6. Hayer-Zillgen M, Brüss M, Bönisch H..  (2002)  Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3.,  136  (1): [PMID:12110607] [10.1038/sj.bjp.0704785]

7. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

Source

Source(2):

• USP Dictionary of USAN and International Drug Names
• TP-search Transporter Database