18-epi-Latrunculol A

ID: ALA521352

PubChem CID: 25150440

Max Phase: Preclinical

Molecular Formula: C22H33NO7S

Molecular Weight: 455.57

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

Standard InChI:  InChI=1S/C22H33NO7S/c1-13-3-6-15-10-16(11-22(28,30-15)19-12-31-21(27)23-19)29-20(26)9-14(2)5-8-18(25)17(24)7-4-13/h4,7,9,13,15-19,24-25,28H,3,5-6,8,10-12H2,1-2H3,(H,23,27)/b7-4-,14-9-/t13-,15+,16+,17-,18-,19+,22+/m0/s1

Standard InChI Key:  JIGPCDTWTJZFFF-BMXFWCHBSA-N

Molfile:  

     RDKit          2D

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   13.0167  -15.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7287  -16.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4407  -15.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1516  -12.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.4456  -15.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8696  -13.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7208  -15.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7320  -17.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0669  -17.6927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3256  -18.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1507  -18.4721    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.4017  -17.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8439  -19.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4417  -16.7875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3000  -15.5542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1542  -15.5500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0118  -13.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7203  -11.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
 15 17  2  0
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  2  3  1  0
 18 19  1  0
  8  9  1  0
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  9 10  2  0
  8 22  1  6
  4 21  1  0
  3 23  1  1
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  1  2  1  0
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 25 26  1  0
 26 27  1  0
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 28 24  1  0
  3 24  1  0
  1  6  1  0
 26 29  2  0
 13 14  1  0
 24 30  1  6
  1 31  1  1
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 21 32  1  6
  6  7  1  0
 11 33  1  1
 15 16  1  0
 12 34  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA521352

   18-EPI-LATRUNCULOL A

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: 455.57

Molecular Weight (Monoisotopic): 455.1978

AlogP: 2.03

#Rotatable Bonds: 1

Polar Surface Area: 125.32

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.35

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: 2.37

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: 3.14

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. Sashidhara KV, White KN, Crews P..  (2009)  A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.,  72  (3): [PMID:19209899] [10.1021/np800817y]

Source

Source(1):

• Scientific Literature