(41R,5aR,6aR,7S,10aS)-7,10a-dimethyl-2-oxo-2,4,5a,6,6a,7,8,9,10,10a-decahydrobenzo[f]oxireno[2,3-i]isochromene-7-carboxylic acid

ID: ALA2269809

PubChem CID: 76323248

Max Phase: Preclinical

Molecular Formula: C16H20O5

Molecular Weight: 292.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(C(=O)O)CCC[C@]2(C)C3=CC(=O)OC[C@]34O[C@@H]4C[C@@H]12

Standard InChI:  InChI=1S/C16H20O5/c1-14-4-3-5-15(2,13(18)19)9(14)6-11-16(21-11)8-20-12(17)7-10(14)16/h7,9,11H,3-6,8H2,1-2H3,(H,18,19)/t9-,11-,14+,15+,16+/m1/s1

Standard InChI Key:  WTKBBGKFHROQGZ-VEVAPSHJSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
    7.4036  -12.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9959  -13.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8165  -13.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7005  -11.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7005  -12.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4036  -11.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1130  -11.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1154  -12.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8163  -12.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8178  -11.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2363  -11.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2420  -10.2645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5316   -9.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8134  -10.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5382   -9.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1066  -10.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4026  -14.1304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6308  -13.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5240  -11.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5301  -12.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2327  -11.8941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  1
  4  5  1  0
  4  6  1  0
  5  1  1  0
  1  8  1  0
  7  6  1  0
  7  8  1  0
  7 10  1  0
  8  9  1  1
 20  9  1  6
 10 19  1  0
 10 14  2  0
 19 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  7 16  1  1
  3 17  1  0
  3 18  2  0
 20 19  1  0
 21 20  1  0
 19 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2269809

   (1R,3R,5R,6S,10S)-6,10-dimethyl-13-oxo-2,14-dioxatetracyclo[9.4.0.01,3.05,10]pentadec-11-ene-6-carboxylic acid

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: 292.33

Molecular Weight (Monoisotopic): 292.1311

AlogP: 1.91

#Rotatable Bonds: 1

Polar Surface Area: 76.13

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.19

CX Basic pKa: ┄

CX LogP: 2.10

CX LogD: -0.94

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.59

Np Likeness Score: 3.28

References

1. Macías FA, Simonet AM, Pacheco PC, Barrero AF, Cabrera E, Jiménez-González D..  (2000)  Natural and synthetic podolactones with potential use as natural herbicide models.,  48  (7): [PMID:10898656] [10.1021/jf990321y]

Source

Source(1):

• Scientific Literature