Macrolactin B

ID: ALA5280440

Max Phase: Preclinical

Molecular Formula: C30H46O10

Molecular Weight: 566.69

Names and Identifiers

Canonical SMILES:  CC1CCC/C=C/CC[C@H](O)C[C@@H](O)C/C=C\C=C\[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C/C=C/C=C\C(=O)O1

Standard InChI:  InChI=1S/C30H46O10/c1-21-13-7-3-2-4-8-14-22(32)19-23(33)15-9-5-10-16-24(17-11-6-12-18-26(34)38-21)39-30-29(37)28(36)27(35)25(20-31)40-30/h2,4-6,9-12,16,18,21-25,27-33,35-37H,3,7-8,13-15,17,19-20H2,1H3/b4-2+,9-5-,11-6+,16-10+,18-12-/t21?,22-,23-,24+,25+,27+,28-,29+,30+/m0/s1

Standard InChI Key:  KMEBAOJKBHMYSK-CGEFVFFESA-N

Molfile:  

 
     RDKit          2D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -2.1438    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736   -2.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -2.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -3.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -3.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -3.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -3.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -3.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1440   -3.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1440   -2.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586    0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736   -2.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -3.7136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    1.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    2.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    2.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    1.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438    1.6506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    2.8883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    3.7136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    2.8884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    0.9962    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
 10  9  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 24 23  2  0
  1 25  2  0
 25 24  1  0
 21 26  1  1
 19 27  1  6
  8 28  2  0
  2 29  1  0
 30 29  1  1
 31 30  1  0
 32 31  1  0
 33 32  1  0
 34 33  1  0
 35 34  1  0
 30 35  1  0
 34 36  1  1
 36 37  1  0
 33 38  1  6
 32 39  1  1
 31 40  1  6
  2 41  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5280440

   ---

Molecule Features

Natural Product: No

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: 566.69

Molecular Weight (Monoisotopic): 566.3091

AlogP: 1.74

#Rotatable Bonds: 3

Polar Surface Area: 166.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 1.95

CX LogD: 1.95

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.22

Np Likeness Score: 2.27

References

1. El-Hossary EM, Cheng C, Hamed MM, Hamed MM, El-Sayed Hamed AN, Ohlsen K, Hentschel U, Abdelmohsen UR..  (2017)  Antifungal potential of marine natural products.,  126  [PMID:27936443] [10.1016/j.ejmech.2016.11.022]

Source

Source(1):

• Scientific Literature