Lycosquarrine A

ID: ALA4791958

PubChem CID: 162672259

Max Phase: Preclinical

Molecular Formula: C25H33NO5

Molecular Weight: 427.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@@]2(O)C[C@H](OC(=O)CCc3ccc(O)cc3)[C@@H]3CCCN4CC[C@H]5O[C@@]52[C@]34C1

Standard InChI:  InChI=1S/C25H33NO5/c1-16-13-23(29)15-20(30-22(28)9-6-17-4-7-18(27)8-5-17)19-3-2-11-26-12-10-21-25(23,31-21)24(19,26)14-16/h4-5,7-8,16,19-21,27,29H,2-3,6,9-15H2,1H3/t16-,19+,20+,21-,23-,24+,25+/m1/s1

Standard InChI Key:  OWIRDPLTQMBZOR-KRVHTBJGSA-N

Molfile:  

 
     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
    2.6002   -3.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6002   -4.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666   -4.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2701   -3.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6007   -2.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9247   -4.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622   -4.4251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577   -5.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9181   -5.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -5.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950   -4.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0624   -3.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0872   -2.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6030   -2.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642   -2.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252   -3.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -2.5029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2622   -2.5011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581   -4.8123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9291   -4.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5988   -4.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2613   -4.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6061   -3.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9352   -4.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5977   -4.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5873   -5.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2491   -5.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9197   -5.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9246   -4.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2623   -4.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5792   -5.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -3.5494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5178   -1.4196    0.0000 C   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  1  0
 16 17  1  1
 15 17  1  0
  5 18  1  6
 11 19  1  1
  3 20  1  6
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 15 32  1  6
 13 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4791958

   ---

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: 427.54

Molecular Weight (Monoisotopic): 427.2359

AlogP: 2.79

#Rotatable Bonds: 4

Polar Surface Area: 82.53

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.70

CX Basic pKa: 9.06

CX LogP: 1.94

CX LogD: 0.65

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.57

Np Likeness Score: 1.71

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