leucettamol A

ID: ALA465243

Cas Number: 151124-32-2

PubChem CID: 44570361

Max Phase: Preclinical

Molecular Formula: C30H52N2O2

Molecular Weight: 472.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](N)[C@@H](O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC[C@H](O)[C@@H](C)N

Standard InChI:  InChI=1S/C30H52N2O2/c1-27(31)29(33)25-23-21-19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-22-24-26-30(34)28(2)32/h3,5-6,8-9,11-12,14-15,17,21,23,27-30,33-34H,4,7,10,13,16,18-20,22,24-26,31-32H2,1-2H3/b5-3-,8-6-,11-9-,14-12-,17-15-,23-21-/t27-,28-,29+,30+/m1/s1

Standard InChI Key:  CXFKWMQQNSTRAS-WGELTRNKSA-N

Molfile:  

     RDKit          2D

 34 33  0  0  0  0  0  0  0  0999 V2000
   -2.1583    1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959    1.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9208    1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6333    1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501    1.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750    1.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043    1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292    1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417    1.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8584    1.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3958    1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1083    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9333    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6458    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3626    1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0748    1.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7915    1.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5037    1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2204    1.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9326    1.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6493    1.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9280    2.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6539    0.5612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3615    1.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5889    1.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3039    1.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179    1.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050    2.5523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878    0.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
 17 18  1  0
  4  5  2  0
 18 19  1  0
  9 10  1  0
 19 20  1  0
  2  3  1  0
 20 21  1  0
 10 11  2  0
 21 22  1  0
  5  6  1  0
 22 23  1  0
 11 12  1  0
 23 24  1  0
  1  2  2  0
 24 25  1  0
 12 13  1  0
 24 26  1  6
  6  7  1  0
 25 27  1  1
 13 14  2  0
 25 28  1  0
  3  4  1  0
  1 29  1  0
 14 15  1  0
 29 30  1  0
  7  8  2  0
 30 31  1  0
 15 16  1  0
 31 32  1  0
 31 33  1  1
 16 17  2  0
 30 34  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA465243

   LEUCETTAMOL A

Molecule Features

Natural Product: No

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: 472.76

Molecular Weight (Monoisotopic): 472.4029

AlogP: 6.42

#Rotatable Bonds: 21

Polar Surface Area: 92.50

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 10.13

CX LogP: 6.34

CX LogD: 1.67

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.11

Np Likeness Score: 1.29

References

1. Tsukamoto S, Takeuchi T, Rotinsulu H, Mangindaan RE, van Soest RW, Ukai K, Kobayashi H, Namikoshi M, Ohta T, Yokosawa H..  (2008)  Leucettamol A: a new inhibitor of Ubc13-Uev1A interaction isolated from a marine sponge, Leucetta aff. microrhaphis.,  18  (24): [PMID:19006668] [10.1016/j.bmcl.2008.10.110]

2. Ushiyama S, Umaoka H, Kato H, Suwa Y, Morioka H, Rotinsulu H, Losung F, Mangindaan RE, de Voogd NJ, Yokosawa H, Tsukamoto S..  (2012)  Manadosterols A and B, sulfonated sterol dimers inhibiting the Ubc13-Uev1A interaction, isolated from the marine sponge Lissodendryx fibrosa.,  75  (8): [PMID:22873794] [10.1021/np300352u]

Source

Source(1):

• Scientific Literature