2-hydroxy-3-((1R,4aR,4bR,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carbonyloxy)-N,N-dimethyl-N-(oxiran-2-ylmethyl)propan-1-aminium

ID: ALA3358322

PubChem CID: 118722793

Max Phase: Preclinical

Molecular Formula: C28H46NO4+

Molecular Weight: 460.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(=O)OCC(O)C[N+](C)(C)CC3CO3)[C@H]2CC1

Standard InChI:  InChI=1S/C28H46NO4/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/h9,14,19,22-25,30H,7-8,10-13,15-18H2,1-6H3/q+1/t22?,23?,24-,25+,27+,28+/m0/s1

Standard InChI Key:  ZJYYTABHXNZXLL-DSEUYVHTSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
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   13.9459  -18.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6512  -18.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6512  -17.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3565  -17.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3530  -18.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0551  -18.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.7686  -17.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4805  -17.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4920  -16.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7854  -15.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.2049  -15.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0549  -17.9576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6516  -20.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8764  -19.4754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2859  -20.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1031  -20.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5126  -20.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5108  -19.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1049  -21.5970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0656  -19.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5144  -22.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2877  -21.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.8734  -22.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1653  -21.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1576  -22.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  2  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
  3 18  1  6
  6 19  1  6
  5 20  1  1
  9 21  1  6
 18 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 26 28  1  0
  3 29  1  0
 28 30  1  0
 28 31  1  0
 28 32  1  0
 32 33  1  0
 34 33  1  0
 35 34  1  0
 33 35  1  0
M  CHG  1  28   1
M  END

Alternative Forms

1. Parent:

   

   ALA3358322

   ---

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: 460.68

Molecular Weight (Monoisotopic): 460.3421

AlogP: 4.50

#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: 0.17

CX LogD: 0.17

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 2.21

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