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

ID: ALA3358323

PubChem CID: 118722794

Max Phase: Preclinical

Molecular Formula: C26H42NO3+

Molecular Weight: 416.63

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)C)CCC[C@]21C

Standard InChI:  InChI=1S/C26H42NO3/c1-18(2)19-9-11-22-20(15-19)10-12-23-25(22,3)13-8-14-26(23,4)24(29)30-17-21(28)16-27(5,6)7/h9,11,15,18,21,23,28H,8,10,12-14,16-17H2,1-7H3/q+1/t21?,23-,25-,26-/m1/s1

Standard InChI Key:  HSTMQVALRULKGG-MVVLOUFASA-N

Molfile:  

     RDKit          2D

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   23.6273  -19.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2275  -19.8027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4444  -19.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4103  -19.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0086  -20.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1915  -20.5301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4241  -21.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0223  -21.9376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5223  -17.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5223  -17.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2274  -18.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.9328  -17.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9294  -17.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6314  -18.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3415  -17.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6384  -16.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3450  -17.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0569  -16.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0684  -15.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3618  -15.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6437  -15.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7812  -15.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4837  -15.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7916  -14.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3436  -17.3921    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.9255  -16.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5140  -18.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2052  -21.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4378  -22.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6060  -22.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
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  5  6  1  0
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  7  8  1  0
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  9 12  1  0
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 11 14  1  0
 13 12  1  0
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 13 17  1  0
 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
M  CHG  1   8   1
M  END

Alternative Forms

1. Parent:

   

   ALA3358323

   ---

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: 416.63

Molecular Weight (Monoisotopic): 416.3159

AlogP: 4.43

#Rotatable Bonds: 6

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 1.12

CX LogD: 1.12

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: 1.72

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