16-epi-latrunculinB

ID: ALA471071

Cas Number: 444911-05-1

PubChem CID: 10000783

Product Number: E390445, Order Now?

Max Phase: Preclinical

Molecular Formula: C20H29NO5S

Molecular Weight: 395.52

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\CC1)O[C@@](O)([C@H]1CSC(=O)N1)C2

Standard InChI:  InChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23)/b5-3-,14-9-/t13-,15-,16-,17-,20-/m1/s1

Standard InChI Key:  NSHPHXHGRHSMIK-WAXGXQFOSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   14.5741  -24.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9200  -25.3748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1825  -26.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0075  -26.1415    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.2533  -25.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7075  -26.8290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5584  -24.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8500  -23.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2792  -23.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0250  -21.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0125  -22.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2917  -22.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7542  -21.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8584  -22.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5875  -22.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7625  -20.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3167  -21.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0542  -19.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4792  -19.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3334  -20.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9917  -23.2667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1292  -23.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6279  -19.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9048  -20.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8871  -21.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1639  -21.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5926  -21.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1463  -22.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8417  -24.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2834  -24.4583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 16  1  0
 19 16  1  0
 20 18  1  0
 12 21  1  6
 14 22  1  1
 15 14  1  0
  1  7  1  0
 20 23  1  0
  2  1  1  0
 23 24  2  0
  3  2  1  0
 24 25  1  0
  4  5  1  0
 25 26  1  0
  5  1  1  0
 25 27  1  1
  6  3  2  0
 26 28  1  0
  3  4  1  0
  7 29  1  1
  1 30  1  6
  8  7  1  0
  9  7  1  0
 10 11  1  0
 11 12  1  0
 12  9  1  0
 13 10  1  0
 14  8  1  0
 15 12  1  0
 16 13  2  0
 17 10  2  0
 28 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA471071

   16-epi-Latrunculin 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: 395.52

Molecular Weight (Monoisotopic): 395.1766

AlogP: 3.30

#Rotatable Bonds: 1

Polar Surface Area: 84.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.36

CX Basic pKa: ┄

CX LogP: 3.79

CX LogD: 3.79

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: 3.13

References

1. Vilozny B, Amagata T, Mooberry SL, Crews P..  (2004)  A new dimension to the biosynthetic products isolated from the sponge Negombata magnifica.,  67  (6): [PMID:15217296] [10.1021/np0340753]

2. 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]

3. Kudrimoti S, Ahmed SA, Daga PR, Wahba AE, Khalifa SI, Doerksen RJ, Hamann MT..  (2009)  Semisynthetic latrunculin B analogs: studies of actin docking support a proposed mechanism for latrunculin bioactivity.,  17  (21): [PMID:19800245] [10.1016/j.bmc.2009.09.012]

Source

Source(1):

• Scientific Literature