10,11-Dihydroxy-4-methyl-6-propyl-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridinium (4-MNP-DHX)

ID: ALA104141

PubChem CID: 10314127

Max Phase: Preclinical

Molecular Formula: C21H25NO2

Molecular Weight: 323.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1Cc2c(C)cccc2[C@@H]2c3cc(O)c(O)cc3CC[C@H]21

Standard InChI:  InChI=1S/C21H25NO2/c1-3-9-22-12-17-13(2)5-4-6-15(17)21-16-11-20(24)19(23)10-14(16)7-8-18(21)22/h4-6,10-11,18,21,23-24H,3,7-9,12H2,1-2H3/t18-,21-/m1/s1

Standard InChI Key:  IURHNFGBYOFFDB-WIYYLYMNSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    5.1706   -1.0427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -1.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5206   -2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5206   -1.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7581   -1.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -0.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7581   -0.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -3.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6956   -2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2831   -3.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5206   -3.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6956   -3.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1706   -2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7581   -3.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5206    0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9956   -1.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6956   -1.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4581   -3.1861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2831   -4.6150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2831   -0.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6956    0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331    1.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4081   -0.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2331   -0.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5831   -1.7572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081   -1.7572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  6  2  0
  5  1  1  0
  6  7  1  0
  7  1  1  0
  8 14  1  0
  9  3  2  0
 10  9  1  0
 11  8  2  0
 12 11  1  0
 13  5  1  0
 14 13  1  0
 15  6  1  0
  1 16  1  0
 17  4  1  0
 18 10  1  0
 19 12  1  0
 20 21  1  0
 21 15  2  0
 22 15  1  0
 23 16  1  0
 24 23  1  0
  2  4  1  0
  3  8  1  0
 20 17  2  0
 10 12  2  0
  5 25  1  1
  2 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA104141

   (6aR,12bS)-4-Methyl-6-propyl-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridine-10,11-diol

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: 323.44

Molecular Weight (Monoisotopic): 323.1885

AlogP: 4.08

#Rotatable Bonds: 2

Polar Surface Area: 43.70

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.57

CX Basic pKa: 8.44

CX LogP: 4.55

CX LogD: 3.66

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: 0.60

References

1. Wilcox RE, Huang WH, Brusniak MY, Wilcox DM, Pearlman RS, Teeter MM, DuRand CJ, Wiens BL, Neve KA..  (2000)  CoMFA-based prediction of agonist affinities at recombinant wild type versus serine to alanine point mutated D2 dopamine receptors.,  43  (16): [PMID:10956209] [10.1021/jm990526y]

2. Knoerzer TA, Watts VJ, Nichols DE, Mailman RB..  (1995)  Synthesis and biological evaluation of a series of substituted benzo[a]phenanthridines as agonists at D1 and D2 dopamine receptors.,  38  (16): [PMID:7636869] [10.1021/jm00016a009]

Source

Source(1):

• Scientific Literature