Aigialone

ID: ALA4130149

Cas Number: 666735-72-4

PubChem CID: 102387950

Max Phase: Preclinical

Molecular Formula: C16H26O5

Molecular Weight: 298.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCC[C@H]1OC2=C(C(=O)[C@@H](C)O2)[C@@H](O)[C@]1(C)O

Standard InChI:  InChI=1S/C16H26O5/c1-4-5-6-7-8-9-11-16(3,19)14(18)12-13(17)10(2)20-15(12)21-11/h10-11,14,18-19H,4-9H2,1-3H3/t10-,11-,14-,16-/m1/s1

Standard InChI Key:  YVCGKKHYXVEPMA-MMYVAXCBSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   21.3790   -4.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3992   -3.1903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1916   -3.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9813   -2.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1916   -4.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8969   -4.6266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8969   -2.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6022   -3.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6066   -4.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8566   -3.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3746   -3.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4845   -4.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7762   -4.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0691   -4.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3608   -4.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6537   -4.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9454   -4.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2383   -4.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8969   -2.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6229   -2.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6737   -3.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1
  4  3  1  0
  3  5  1  0
  3  7  1  0
  5  6  1  0
  6  9  1  0
  8  7  1  0
  8  9  2  0
  9  1  1  0
  1 10  1  0
 10 11  1  0
 11  8  1  0
  5 12  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7 19  1  6
 11 20  2  0
 10 21  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4130149

   (-)-Aigialone

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: 298.38

Molecular Weight (Monoisotopic): 298.1780

AlogP: 2.06

#Rotatable Bonds: 6

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.58

CX Basic pKa: ┄

CX LogP: 2.86

CX LogD: 2.84

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: 2.29

References

1. Silva GH, Zeraik ML, de Oliveira CM, Teles HL, Trevisan HC, Pfenning LH, Nicolli CP, Young MCM, Mascarenhas YP, Abreu LM, Saraiva AC, Medeiros AI, Bolzani VDS, Araujo AR..  (2017)  Lactone Derivatives Produced by a Phaeoacremonium sp., an Endophytic Fungus from Senna spectabilis.,  80  (5): [PMID:28425292] [10.1021/acs.jnatprod.5b00828]

Source

Source(1):

• Scientific Literature