Lycosquarrine M

ID: ALA4762857

PubChem CID: 162660031

Max Phase: Preclinical

Molecular Formula: C16H22N2O2

Molecular Weight: 274.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@H]2Cc3[nH]c(=O)ccc3[C@]3(C1)NCC[C@@H](O)[C@H]23

Standard InChI:  InChI=1S/C16H22N2O2/c1-9-6-10-7-12-11(2-3-14(20)18-12)16(8-9)15(10)13(19)4-5-17-16/h2-3,9-10,13,15,17,19H,4-8H2,1H3,(H,18,20)/t9-,10+,13-,15+,16+/m1/s1

Standard InChI Key:  PRZIYDFKKSMMTD-PDSBVLEXSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   24.4868  -20.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4868  -21.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1632  -22.0683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1632  -20.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8396  -20.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8362  -21.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1898  -20.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5121  -20.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1863  -21.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5058  -22.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5000  -22.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1730  -23.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8494  -22.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8569  -22.0783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5248  -23.2564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1513  -21.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5145  -19.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7333  -19.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9396  -20.1202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1861  -20.1161    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.2675  -19.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9032  -19.7488    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  1  0
 13 15  2  0
  6 16  1  1
  8 17  1  0
 17 18  1  0
 18 16  1  0
  5 19  1  1
  8 20  1  6
 18 21  1  6
  4 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4762857

   ---

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: 1.14

#Rotatable Bonds: ┄

Polar Surface Area: 65.12

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.22

CX Basic pKa: 9.33

CX LogP: -0.22

CX LogD: -2.03

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: 1.86

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