Latrunculone B

ID: ALA485952

PubChem CID: 25150348

Max Phase: Preclinical

Molecular Formula: C22H31NO6S

Molecular Weight: 437.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C1=C/C(=O)O[C@@H]2C[C@@H](CC[C@H](C)/C=C\CC(=O)CC1)O[C@@](O)([C@@H]1CSC(=O)N1)C2

Standard InChI:  InChI=1S/C22H31NO6S/c1-14-4-3-5-16(24)8-6-15(2)10-20(25)28-18-11-17(9-7-14)29-22(27,12-18)19-13-30-21(26)23-19/h3-4,10,14,17-19,27H,5-9,11-13H2,1-2H3,(H,23,26)/b4-3-,15-10-/t14-,17-,18-,19+,22-/m1/s1

Standard InChI Key:  GCLFJDBFHQMHMU-PPLVVCHYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   13.1708  -23.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1708  -24.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8829  -25.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5949  -24.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8829  -23.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4552  -23.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4527  -22.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7371  -22.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7346  -21.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4479  -21.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1636  -21.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8768  -21.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5925  -21.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3058  -21.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0215  -21.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7347  -21.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0239  -22.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3106  -22.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3130  -23.5021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5949  -22.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5998  -23.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0238  -22.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8750  -24.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8862  -25.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2211  -26.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4798  -27.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3048  -27.2471    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5559  -26.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9981  -27.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5958  -25.5625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4542  -24.3292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3083  -24.3250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8744  -20.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  1  5  1  0
 15 17  2  0
  7  8  1  0
 17 18  1  0
  2  3  1  0
 18 19  1  0
  8  9  1  0
 18 20  2  0
  3  4  1  0
 21 19  1  0
  9 10  2  0
  8 22  1  6
  4 21  1  0
  3 23  1  1
 24 25  1  0
 10 11  1  0
 21  5  1  0
 11 12  1  0
  1  2  1  0
 12 13  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
  3 24  1  0
  1  6  1  0
 26 29  2  0
 13 14  1  0
 24 30  1  1
  1 31  1  1
 14 15  1  0
 21 32  1  6
  6  7  1  0
 12 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA485952

   LATRUNCULONE B

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 437.56

Molecular Weight (Monoisotopic): 437.1872

AlogP: 3.26

#Rotatable Bonds: 1

Polar Surface Area: 101.93

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.36

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.48

Np Likeness Score: 3.00

References

1. Amagata T, Johnson TA, Cichewicz RH, Tenney K, Mooberry SL, Media J, Edelstein M, Valeriote FA, Crews P..  (2008)  Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.,  51  (22): [PMID:18942825] [10.1021/jm8008585]

2. Johnson TA, Sohn J, Inman WD, Estee SA, Loveridge ST, Vervoort HC, Tenney K, Liu J, Ang KK, Ratnam J, Bray WM, Gassner NC, Shen YY, Lokey RS, McKerrow JH, Boundy-Mills K, Nukanto A, Kanti A, Julistiono H, Kardono LB, Bjeldanes LF, Crews P..  (2011)  Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.,  74  (12): [PMID:22129061] [10.1021/np200673b]

Source

Source(1):

• Scientific Literature