gloeolactone

ID: ALA472019

PubChem CID: 10589748

Max Phase: Preclinical

Molecular Formula: C18H28O3

Molecular Weight: 292.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Gloeolactone | gloeolactone|CHEMBL472019|CHEBI:202407|DTXSID901046925|10-[(E)-2-[(2R,3R)-3-[(Z)-pent-2-enyl]oxiran-2-yl]ethenyl]oxecan-2-one

Canonical SMILES:  CC/C=C\C[C@H]1O[C@@H]1/C=C/C1CCCCCCCC(=O)O1

Standard InChI:  InChI=1S/C18H28O3/c1-2-3-7-11-16-17(21-16)14-13-15-10-8-5-4-6-9-12-18(19)20-15/h3,7,13-17H,2,4-6,8-12H2,1H3/b7-3-,14-13+/t15?,16-,17-/m1/s1

Standard InChI Key:  NQKZDMRQSOUOJH-OULGUUDZSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    6.3114   -2.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5930   -2.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0187   -3.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0237   -2.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3045   -4.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5945   -3.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8876   -3.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8825   -4.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5924   -5.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3060   -4.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742   -3.5809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -2.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661   -2.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4470   -2.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -1.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6209   -2.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466   -3.1611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132   -2.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9064   -1.9636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9208   -3.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2090   -4.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4075   -3.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786   -4.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 12  1  0
  1  4  1  0
 12 13  2  0
  2  6  1  0
 13 14  1  0
 15 14  1  0
 16 15  1  0
 14 16  1  0
  5  3  1  0
  3  4  1  0
  5 10  1  0
 14 17  1  1
  6  7  1  0
 16 18  1  0
  7  8  1  0
 16 19  1  6
  8  9  1  0
 18 20  1  0
  9 10  1  0
 20 21  2  0
 21 22  1  0
  7 11  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472019

   GLOEOLACTONE

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: 292.42

Molecular Weight (Monoisotopic): 292.2038

AlogP: 4.32

#Rotatable Bonds: 5

Polar Surface Area: 38.83

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.71

CX LogD: 4.71

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.43

Np Likeness Score: 2.36

References

1. Stierle DB, Stierle AA, Bugni T, Loewen G..  (1998)  Gloeolactone, a New Epoxy Lactone from a Blue-Green Alga,  61  (2): [PMID:9548854] [10.1021/np9703398]

Source

Source(1):

• Scientific Literature