Methyl (4aR,10aS)-9-((2-Hydroxyethyl)thio)-7-isopropyl-1,1-dimethyl-5,6-dioxo-1,3,4,5,6,9,10,10a-octahydrophenanthrene-4a(2H)-carboxylate

ID: ALA4531257

PubChem CID: 155546213

Max Phase: Preclinical

Molecular Formula: C23H32O5S

Molecular Weight: 420.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]12CCCC(C)(C)[C@@H]1CC(SCCO)C1=C2C(=O)C(=O)C(C(C)C)=C1

Standard InChI:  InChI=1S/C23H32O5S/c1-13(2)14-11-15-16(29-10-9-24)12-17-22(3,4)7-6-8-23(17,21(27)28-5)18(15)20(26)19(14)25/h11,13,16-17,24H,6-10,12H2,1-5H3/t16?,17-,23+/m0/s1

Standard InChI Key:  YARIKFXTFDZVQR-KMXYETGPSA-N

Molfile:  

 
     RDKit          2D

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   33.1791  -15.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4710  -15.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7588  -15.9423    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.0507  -15.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0507  -14.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7626  -14.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7555  -13.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4677  -13.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1758  -13.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4677  -12.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0516  -13.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0516  -12.2610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3437  -13.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1316  -12.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3429  -14.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6310  -14.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4189  -13.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8307  -13.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6311  -13.7115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4190  -12.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6310  -15.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8472  -16.3225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.3429  -15.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9233  -15.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3339  -16.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5145  -16.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2155  -15.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2155  -14.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9233  -14.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8871  -15.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 15 13  1  0
 16 15  1  0
 16 17  1  1
 17 18  2  0
 17 19  1  0
 19 20  1  0
 21 16  1  0
 21 22  1  6
 21 23  1  0
 23  4  1  0
 24 21  1  0
 24 25  1  0
 24 26  1  0
 27 24  1  0
 28 27  1  0
 28 29  1  0
 16 29  1  0
  5 15  2  0
  1 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531257

   ---

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: 420.57

Molecular Weight (Monoisotopic): 420.1970

AlogP: 3.50

#Rotatable Bonds: 5

Polar Surface Area: 80.67

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: 1.86

References

1. Han S, Li X, Xia Y, Yu Z, Cai N, Malwal SR, Han X, Oldfield E, Zhang Y..  (2019)  Farnesyl Pyrophosphate Synthase as a Target for Drug Development: Discovery of Natural-Product-Derived Inhibitors and Their Activity in Pancreatic Cancer Cells.,  62  (23): [PMID:31725297] [10.1021/acs.jmedchem.9b01405]

Source

Source(1):

• Scientific Literature