Lycosquarrine O

ID: ALA4745068

PubChem CID: 162647546

Max Phase: Preclinical

Molecular Formula: C16H22N2O2

Molecular Weight: 274.36

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H22N2O2/c1-10-8-15-11-4-2-6-17-12(11)9-16(20,14(10)19)13(15)5-3-7-18-15/h2,4,6,10,13-14,18-20H,3,5,7-9H2,1H3/t10-,13-,14-,15-,16+/m0/s1

Standard InChI Key:  HMTDCFFZFKBTFS-CUXOXCPVSA-N

Molfile:  

 
     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
    2.6002   -4.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6002   -5.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -5.9061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -4.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529   -4.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495   -5.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3031   -4.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6254   -4.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2996   -5.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191   -5.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133   -6.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863   -7.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9627   -6.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9702   -5.9160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2646   -5.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6278   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8466   -3.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529   -3.9580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2994   -3.9539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808   -2.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2068   -2.9900    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  6
M  END

Alternative Forms

1. Parent:

   

   ALA4745068

   ---

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: 274.36

Molecular Weight (Monoisotopic): 274.1681

AlogP: 0.96

#Rotatable Bonds: ┄

Polar Surface Area: 65.38

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 8.65

CX LogP: 0.31

CX LogD: -0.96

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: 1.32

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