esculentin A

ID: ALA3586098

PubChem CID: 122180083

Max Phase: Preclinical

Molecular Formula: C24H32O6

Molecular Weight: 416.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C/C(C)=C/C[C@]1(C)[C@H](C)CC[C@@]23C(=CC(=O)C[C@@H]12)[C@@H](OC(C)=O)O[C@H]3OC(C)=O

Standard InChI:  InChI=1S/C24H32O6/c1-7-14(2)8-10-23(6)15(3)9-11-24-19(12-18(27)13-20(23)24)21(28-16(4)25)30-22(24)29-17(5)26/h7-8,12,15,20-22H,1,9-11,13H2,2-6H3/b14-8+/t15-,20+,21+,22-,23-,24-/m1/s1

Standard InChI Key:  RSQJWXPIJIXDDX-VAPGVGGTSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.9679   -1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976   -2.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2622   -3.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3161   -3.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885    1.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573    2.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739    1.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -0.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699    2.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739    0.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -0.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6508   -2.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3016   -2.4624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302    2.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899    4.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4756    4.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0354    5.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2164    3.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2233    5.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    2.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646   -2.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300   -2.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439   -1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2078   -3.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7328    2.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    2.6885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0183    1.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  5  6  1  0
  5  7  1  0
  6 14  2  0
  8  7  1  0
  8 13  1  0
  8 12  1  0
 13  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 13 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 21 23  2  0
 11 24  1  6
 15 25  1  6
 25 26  1  0
 26 27  1  0
 26 28  2  0
  5 29  2  0
  8 30  1  6
 12 31  1  1
 17 16  1  0
 17  1  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3586098

   ---

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: 416.51

Molecular Weight (Monoisotopic): 416.2199

AlogP: 4.26

#Rotatable Bonds: 5

Polar Surface Area: 78.90

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: 3.36

References

1. De Ford C, Calderón C, Sehgal P, Fedosova NU, Murillo R, Olesen C, Nissen P, Møller JV, Merfort I..  (2015)  Discovery of Tricyclic Clerodane Diterpenes as Sarco/Endoplasmic Reticulum Ca(2+)-ATPase Inhibitors and Structure-Activity Relationships.,  78  (6): [PMID:25993619] [10.1021/acs.jnatprod.5b00062]

Source

Source(1):

• Scientific Literature