Lycosquarrine B

ID: ALA4779502

PubChem CID: 162663257

Max Phase: Preclinical

Molecular Formula: C25H33NO4

Molecular Weight: 411.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@H]2C[C@H](OC(=O)CCc3ccc(O)cc3)[C@@H]3CCCN4CC[C@H]5O[C@]25[C@]34C1

Standard InChI:  InChI=1S/C25H33NO4/c1-16-13-18-14-21(29-23(28)9-6-17-4-7-19(27)8-5-17)20-3-2-11-26-12-10-22-25(18,30-22)24(20,26)15-16/h4-5,7-8,16,18,20-22,27H,2-3,6,9-15H2,1H3/t16-,18+,20+,21+,22-,24+,25-/m1/s1

Standard InChI Key:  SRCHVEIHBGSEBY-LWISLXJSSA-N

Molfile:  

 
     RDKit          2D

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   13.2855   -4.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.9389   -5.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5952   -5.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2660   -5.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2708   -3.3957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5958   -4.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2542   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2438   -5.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9014   -5.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5679   -5.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5728   -4.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9146   -4.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2234   -5.7259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3256   -3.6402    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1984   -1.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9806   -2.5713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1 15  1  0
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 16 17  1  1
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 11 18  1  1
  3 19  1  6
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 27 30  1  0
 15 31  1  6
 13 32  1  6
  5 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4779502

   ---

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: 411.54

Molecular Weight (Monoisotopic): 411.2410

AlogP: 3.68

#Rotatable Bonds: 4

Polar Surface Area: 62.30

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.28

CX Basic pKa: 9.89

CX LogP: 2.91

CX LogD: 1.43

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.60

Np Likeness Score: 1.74

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