Lycosquarrine R

ID: ALA4758865

PubChem CID: 162657859

Max Phase: Preclinical

Molecular Formula: C16H20N2O2

Molecular Weight: 272.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1CC2=[N+]([O-])CCC[C@]23c2cccnc2C[C@@H]3[C@@H]1O

Standard InChI:  InChI=1S/C16H20N2O2/c1-10-8-14-16(5-3-7-18(14)20)11-4-2-6-17-13(11)9-12(16)15(10)19/h2,4,6,10,12,15,19H,3,5,7-9H2,1H3/t10-,12+,15+,16+/m0/s1

Standard InChI Key:  IROBVBVAUUAKPT-PBXWNFIWSA-N

Molfile:  

 
     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   24.7427   -5.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7427   -6.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4581   -6.9103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1692   -6.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1692   -5.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4581   -5.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7873   -7.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5014   -7.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2213   -7.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2184   -6.2124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7886   -6.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4995   -5.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3193   -4.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5030   -4.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5067   -5.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7508   -4.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9432   -4.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4581   -7.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4273   -3.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4165   -3.6568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9123   -5.6313    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  6
 11  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 12  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  5  1  0
  5 11  1  0
  4 15  1  0
 14 16  1  0
 16 17  1  0
 15 17  1  0
  3 18  1  0
 17 19  1  6
 16 20  1  1
 14 21  1  6
M  CHG  2   3   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4758865

   ---

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: 272.35

Molecular Weight (Monoisotopic): 272.1525

AlogP: 1.64

#Rotatable Bonds: ┄

Polar Surface Area: 59.19

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.36

CX Basic pKa: 5.33

CX LogP: -3.17

CX LogD: 0.13

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.58

Np Likeness Score: 1.11

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