Lycosquarrine G

ID: ALA4749507

PubChem CID: 162650800

Max Phase: Preclinical

Molecular Formula: C18H28N2O3

Molecular Weight: 320.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)NC1=C2CCC[N+]3([O-])CCC[C@]4(O)[C@H](C1)C[C@@H](C)C[C@]243

Standard InChI:  InChI=1S/C18H28N2O3/c1-12-9-14-10-16(19-13(2)21)15-5-3-7-20(23)8-4-6-18(14,22)17(15,20)11-12/h12,14,22H,3-11H2,1-2H3,(H,19,21)/t12-,14+,17+,18+,20?/m1/s1

Standard InChI Key:  OAWITTWRVWHOFK-ZMDDYQIESA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   16.6534  -11.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6534  -12.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4189  -12.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4224  -11.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7282  -10.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0316  -12.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3402  -12.5144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3356  -13.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0208  -13.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7163  -13.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7225  -12.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467  -11.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8379  -10.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7305  -10.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3421  -10.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0320  -11.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4186  -10.5203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3439   -9.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1016  -12.5345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7960  -12.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4828  -12.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8035  -11.3483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7252  -11.7172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6534  -12.9058    0.0000 O   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  2  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
 13 18  1  6
  3 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 16 23  1  1
  7 24  1  0
M  CHG  2   7   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4749507

   ---

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: 320.43

Molecular Weight (Monoisotopic): 320.2100

AlogP: 2.20

#Rotatable Bonds: 1

Polar Surface Area: 72.39

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.59

CX Basic pKa: 2.97

CX LogP: -0.53

CX LogD: -0.53

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.57

Np Likeness Score: 1.35

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