(4R,6aR,7S,10aS)-methyl 4-isopropyl-7,10a-dimethyl-2-oxo-4,6,6a,7,8,9,10,10a-octahydro-2H-benzo[f]isochromene-7-carboxylate

ID: ALA2269810

PubChem CID: 15479301

Max Phase: Preclinical

Molecular Formula: C20H28O4

Molecular Weight: 332.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H28O4/c1-12(2)17-13-7-8-15-19(3,14(13)11-16(21)24-17)9-6-10-20(15,4)18(22)23-5/h7,11-12,15,17H,6,8-10H2,1-5H3/t15-,17-,19-,20+/m1/s1

Standard InChI Key:  FCETVXGBHNPYHQ-QOJCHSLYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    1.2702  -12.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8613  -13.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6826  -13.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5648  -11.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5648  -11.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702  -10.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797  -11.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813  -11.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6853  -12.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986  -11.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6862  -10.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965  -11.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1079  -10.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144   -9.9288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -9.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -9.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4085   -8.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728  -10.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695  -13.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998  -13.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4523  -13.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120  -11.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8049  -11.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233  -10.7670    0.0000 C   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 11  1  0
  8  9  1  1
  9 10  1  0
 10 12  2  0
 11 12  1  0
 11 16  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  1
  3 19  1  0
  3 20  2  0
 19 21  1  0
 13 22  1  6
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269810

   methyl (4R,6aR,7S,10aS)-7,10a-dimethyl-2-oxo-4-propan-2-yl-4,6,6a,8,9,10-hexahydrobenzo[f]isochromene-7-carboxylate

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: 332.44

Molecular Weight (Monoisotopic): 332.1988

AlogP: 3.81

#Rotatable Bonds: 2

Polar Surface Area: 52.60

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.06

CX LogD: 4.06

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: 2.75

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