Lycosquarrine E

ID: ALA4783681

PubChem CID: 162666320

Max Phase: Preclinical

Molecular Formula: C16H25NO4

Molecular Weight: 295.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@@]2(O)C[C@@H]3O[C@H]4CC[N+]5([O-])CCC[C@@H]3[C@@]5(C1)[C@]42O

Standard InChI:  InChI=1S/C16H25NO4/c1-10-7-14(18)9-12-11-3-2-5-17(20)6-4-13(21-12)16(14,19)15(11,17)8-10/h10-13,18-19H,2-9H2,1H3/t10-,11+,12+,13+,14-,15+,16+,17?/m1/s1

Standard InChI Key:  SRCRXDGGNRIFEO-CWDHHZBKSA-N

Molfile:  

 
     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
    3.2069  -11.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069  -12.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8114  -12.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149  -11.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1579  -11.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025  -12.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483  -12.7249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8437  -13.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4959  -13.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501  -13.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1522  -12.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167  -11.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5069  -10.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602  -10.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8502  -11.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5030  -11.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8070  -10.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8029  -13.1081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5530  -12.6535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9939  -12.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424  -10.4254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027  -13.0957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6101  -10.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386   -9.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1 15  1  0
  2  7  1  0
 16  6  1  0
 16  5  1  0
 11  3  1  0
  3  4  1  0
  4  5  1  0
  6  7  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  1
 12 13  1  0
  5 14  1  0
 14 13  1  0
 16 15  1  0
  5 17  1  6
 11 18  1  1
  3 19  1  6
 15 20  1  0
  3 20  1  0
 15 21  1  6
  7 22  1  0
 16 23  1  1
 13 24  1  6
M  CHG  2   7   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4783681

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 295.38

Molecular Weight (Monoisotopic): 295.1784

AlogP: 0.92

#Rotatable Bonds: ┄

Polar Surface Area: 72.75

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.07

CX Basic pKa: 3.15

CX LogP: -1.04

CX LogD: -1.04

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 1.78

References

1. Zhu X,Xia D,Zhou Z,Xie S,Shi Z,Chen G,Wang L,Pan K.  (2020)  Lycosquarrines A-R, Lycopodium Alkaloids from Phlegmariurus squarrosus.,  83  (10): [PMID:32941036] [10.1021/acs.jnatprod.9b00815]

Source

Source(1):

• Scientific Literature