4-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)thiazolidine-2,5-dione

ID: ALA4534162

PubChem CID: 155546823

Max Phase: Preclinical

Molecular Formula: C19H27NO4S

Molecular Weight: 365.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C/C=C1/NC(=O)SC1=O

Standard InChI:  InChI=1S/C19H27NO4S/c1-11-4-7-14-18(2,9-8-15(22)19(14,3)10-21)12(11)5-6-13-16(23)25-17(24)20-13/h6,12,14-15,21-22H,1,4-5,7-10H2,2-3H3,(H,20,24)/b13-6+/t12-,14+,15-,18+,19+/m1/s1

Standard InChI Key:  FDZMNHNVFFMFSE-LABSEPMPSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   14.3669  -19.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9624  -18.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5493  -19.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0979  -15.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0979  -14.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7589  -14.1316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5023  -13.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6768  -13.3462    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.4244  -14.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6390  -14.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3861  -15.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3861  -16.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3784  -18.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0879  -17.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0915  -17.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6683  -17.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6726  -17.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9730  -16.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2647  -17.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2605  -17.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8032  -16.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6682  -16.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6640  -18.7211    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5465  -18.3012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9560  -19.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9820  -12.6847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
  4 11  1  0
 12 11  1  6
 12 17  1  0
 12 15  1  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 16 17  1  0
 16  2  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 15 21  2  0
 17 22  1  6
 16 23  1  1
 20 24  1  6
  1 25  1  0
  7 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534162

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 365.50

Molecular Weight (Monoisotopic): 365.1661

AlogP: 2.99

#Rotatable Bonds: 3

Polar Surface Area: 86.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.38

CX Basic pKa: ┄

CX LogP: 2.23

CX LogD: 2.22

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: 2.42

References

1. Kandanur SGS, Tamang N, Golakoti NR, Nanduri S..  (2019)  Andrographolide: A natural product template for the generation of structurally and biologically diverse diterpenes.,  176  [PMID:31151068] [10.1016/j.ejmech.2019.05.022]

Source

Source(1):

• Scientific Literature