(-)-Lyngbyatoxin

ID: ALA5172923

Cas Number: 70497-14-2

PubChem CID: 91706

Max Phase: Preclinical

Molecular Formula: C27H39N3O2

Molecular Weight: 437.63

Names and Identifiers

Canonical SMILES:  C=C[C@@](C)(CCC=C(C)C)c1ccc2c3c(c[nH]c13)C[C@@H](CO)NC(=O)[C@H](C(C)C)N2C

Standard InChI:  InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27-/m0/s1

Standard InChI Key:  KISDGNGREAJPQR-OICBGKIFSA-N

Molfile:  

 
     RDKit          2D

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    0.2627    0.9818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730    1.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4463    1.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0309   -0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4463    2.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4169    1.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291    1.9771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6113   -1.5462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584   -0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8852   -2.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4651   -1.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0931   -3.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -2.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3278   -2.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2572   -2.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8370   -1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291   -1.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6248   -0.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  4  9  2  0
  6 10  1  6
 10 11  1  0
  3 12  1  1
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 12 14  1  0
  2 15  1  0
  8 16  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
  1 19  1  0
 16 20  1  0
  8 21  1  0
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 21 22  2  0
 22 20  1  0
 17 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  6
 23 27  1  0
 27 28  2  0
 25 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5172923

   Lyngbyatoxin a

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 437.63

Molecular Weight (Monoisotopic): 437.3042

AlogP: 4.85

#Rotatable Bonds: 7

Polar Surface Area: 68.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.14

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: 2.25

References

1. Mendoza M, Tran U, Zhang GC, Leister J, To K, Malepeai-Tofaeono T, Ondrus AE, Billingsley KL..  (2022)  Indolactam Dipeptides as Nanomolar Gli Inhibitors.,  13  (7.0): [PMID:35859880] [10.1021/acsmedchemlett.1c00562]

2. Xu J, Zhang T, Yao J, Lu J, Liu Z, Ding L..  (2020)  Recent advances in chemistry and bioactivity of marine cyanobacteria Moorea species.,  201  [PMID:32652435] [10.1016/j.ejmech.2020.112473]

Source

Source(1):

• Scientific Literature