Lycosquarrine F

ID: ALA4784733

PubChem CID: 162665390

Max Phase: Preclinical

Molecular Formula: C16H25NO3

Molecular Weight: 279.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1C[C@]23C4=CCCN2CCC[C@@H]3[C@H](O)[C@@H](O)[C@@H]4[C@@H]1O

Standard InChI:  InChI=1S/C16H25NO3/c1-9-8-16-10-4-2-6-17(16)7-3-5-11(16)14(19)15(20)12(10)13(9)18/h4,9,11-15,18-20H,2-3,5-8H2,1H3/t9-,11+,12-,13+,14-,15-,16+/m0/s1

Standard InChI Key:  WKXWYSDPWUOGKQ-SIOVJARSSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    9.7238  -11.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7238  -11.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3613  -11.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3648  -11.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7036  -10.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0359  -11.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3775  -12.3040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3730  -13.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0293  -13.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6918  -13.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6980  -12.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1819  -11.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2066  -10.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7060  -10.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3795  -10.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0364  -11.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3610  -10.4006    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3569  -12.6871    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0189  -12.3247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0341  -10.7888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6423   -9.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2849   -9.6431    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  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  2  0
  5 17  1  6
 11 18  1  6
  3 19  1  1
  4 20  1  6
 13 21  1  6
 14 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4784733

   ---

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: 279.38

Molecular Weight (Monoisotopic): 279.1834

AlogP: 0.52

#Rotatable Bonds: ┄

Polar Surface Area: 63.93

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.49

CX Basic pKa: 9.37

CX LogP: -0.36

CX LogD: -2.32

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.57

Np Likeness Score: 2.28

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