Lycosquarrine N

ID: ALA4743265

PubChem CID: 162647334

Max Phase: Preclinical

Molecular Formula: C16H22N2O

Molecular Weight: 258.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1C[C@@]23NCCC[C@@H]2[C@H](Cc2ncccc23)[C@@H]1O

Standard InChI:  InChI=1S/C16H22N2O/c1-10-9-16-12(4-3-7-18-16)11(15(10)19)8-14-13(16)5-2-6-17-14/h2,5-6,10-12,15,18-19H,3-4,7-9H2,1H3/t10-,11-,12+,15+,16+/m0/s1

Standard InChI Key:  IZSWVBHUBNPZTL-YYFFNPIBSA-N

Molfile:  

 
     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   31.8746  -20.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8746  -21.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5510  -22.1508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5510  -20.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2274  -20.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2239  -21.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5775  -20.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8999  -20.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5741  -21.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8935  -22.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8877  -22.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5607  -23.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2371  -22.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2446  -22.1608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5391  -21.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9022  -19.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1210  -19.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3274  -20.2028    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.5738  -20.1987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.6553  -19.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4812  -19.2347    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  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  1
  8 16  1  0
 16 17  1  0
 17 15  1  0
  5 18  1  1
  8 19  1  6
 17 20  1  6
 16 21  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4743265

   ---

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: 258.37

Molecular Weight (Monoisotopic): 258.1732

AlogP: 1.85

#Rotatable Bonds: ┄

Polar Surface Area: 45.15

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.11

CX LogP: 1.20

CX LogD: -0.52

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.75

Np Likeness Score: 1.52

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