2-hydroxy-3-((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carbonyloxy)-N,N-dimethyl-N-(oxiran-2-ylmethyl)propan-1-aminium

ID: ALA3358326

PubChem CID: 118722797

Max Phase: Preclinical

Molecular Formula: C28H44NO4+

Molecular Weight: 458.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc2c(c1)CC[C@H]1[C@](C)(C(=O)OCC(O)C[N+](C)(C)CC3CO3)CCC[C@]21C

Standard InChI:  InChI=1S/C28H44NO4/c1-19(2)20-8-10-24-21(14-20)9-11-25-27(24,3)12-7-13-28(25,4)26(31)33-17-22(30)15-29(5,6)16-23-18-32-23/h8,10,14,19,22-23,25,30H,7,9,11-13,15-18H2,1-6H3/q+1/t22?,23?,25-,27-,28-/m1/s1

Standard InChI Key:  DRSIARPQBQOMIB-FMMIJXDPSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   10.1313  -27.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7314  -28.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9483  -27.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9143  -28.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5126  -28.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6954  -28.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9280  -29.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5263  -30.3159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0262  -25.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0262  -26.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7314  -26.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7315  -25.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4368  -25.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4333  -26.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1354  -26.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8454  -26.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1423  -25.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5608  -25.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8658  -23.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1477  -24.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2852  -23.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9877  -24.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2956  -23.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8476  -25.7704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4295  -24.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0180  -27.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7092  -30.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9417  -31.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1100  -31.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2929  -31.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5871  -30.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5788  -31.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  9 10  1  0
  9 12  1  0
 10 11  1  0
 11 14  1  0
 13 12  1  0
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 14 15  1  0
 15 16  1  0
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 17 18  2  0
 17 22  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 14 26  1  6
 13 27  1  1
 11 28  1  0
 11  1  1  6
  8 29  1  0
  8 30  1  0
  8 31  1  0
 31 32  1  0
 33 32  1  0
 34 33  1  0
 32 34  1  0
M  CHG  1   8   1
M  END

Alternative Forms

1. Parent:

   

   ALA3358326

   ---

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: 458.66

Molecular Weight (Monoisotopic): 458.3265

AlogP: 4.20

#Rotatable Bonds: 8

Polar Surface Area: 59.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 0.96

CX LogD: 0.96

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: 1.59

References

1. Wang H, Nguyen TT, Li S, Liang T, Zhang Y, Li J..  (2015)  Quantitative structure-activity relationship of antifungal activity of rosin derivatives.,  25  (2): [PMID:25466709] [10.1016/j.bmcl.2014.11.034]

Source

Source(1):

• Scientific Literature