serratamolide C

ID: ALA464875

PubChem CID: 24862329

Max Phase: Preclinical

Molecular Formula: C28H50N2O8

Molecular Weight: 542.71

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Serratamolide C | CHEMBL464875

Canonical SMILES:  CCCCCCCCC[C@@H]1CC(=O)N[C@@H](CO)C(=O)O[C@H](CCCCCCC)CC(=O)N[C@@H](CO)C(=O)O1

Standard InChI:  InChI=1S/C28H50N2O8/c1-3-5-7-9-10-12-14-16-22-18-26(34)30-23(19-31)27(35)37-21(15-13-11-8-6-4-2)17-25(33)29-24(20-32)28(36)38-22/h21-24,31-32H,3-20H2,1-2H3,(H,29,33)(H,30,34)/t21-,22-,23+,24+/m1/s1

Standard InChI Key:  QKEQCKGYZLGUCK-LWSSLDFYSA-N

Molfile:  

     RDKit          2D

 38 38  0  0  0  0  0  0  0  0999 V2000
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   10.0192   -6.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4202   -6.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1614   -6.8853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3451   -6.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4155   -7.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1203   -7.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4583   -8.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1595   -7.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2372   -8.3696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4169   -8.3061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1686   -9.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5668   -9.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8893   -9.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7940   -8.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2567   -5.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3318   -9.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7049   -6.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9867   -7.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8700   -8.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5884   -7.9547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4382   -9.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1529   -5.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8476   -6.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5803   -5.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2750   -6.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0076   -5.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7024   -6.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7408   -9.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0104   -9.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3131   -9.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5827   -9.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4351   -5.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1298   -6.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8625   -5.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853   -9.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1617   -9.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 18  2  0
  3  5  1  0
  6 19  1  6
  4  6  1  0
 19 20  1  0
  5  7  1  0
  9 21  1  6
  6  8  1  0
 21 22  1  0
  7  9  1  0
 12 23  1  1
  8 10  1  0
  3 24  1  1
  9 11  1  0
 24 25  1  0
 12 10  1  0
 25 26  1  0
 11 13  1  0
 26 27  1  0
 12 14  1  0
 27 28  1  0
 13 14  1  0
 28 29  1  0
 23 30  1  0
  8 15  2  0
 30 31  1  0
  1  2  1  0
 31 32  1  0
  2 16  2  0
 32 33  1  0
  1  3  1  0
 33 37  1  0
  7 17  2  0
 29 34  1  0
  2  4  1  0
 34 35  1  0
 35 36  1  0
 37 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA464875

   SERRATAMOLIDE C

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: 542.71

Molecular Weight (Monoisotopic): 542.3567

AlogP: 3.06

#Rotatable Bonds: 16

Polar Surface Area: 151.26

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.55

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.17

Np Likeness Score: 1.04

References

1. Dwivedi D, Jansen R, Molinari G, Nimtz M, Johri BN, Wray V..  (2008)  Antimycobacterial serratamolides and diacyl peptoglucosamine derivatives from Serratia sp.,  71  (4): [PMID:18303848] [10.1021/np7007126]

Source

Source(1):

• Scientific Literature