Methyl (4aR,10aS)-5,6-Dihydroxy-7-isopropyl-9-methoxy-1,1-dimethyl-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylate

ID: ALA4538938

PubChem CID: 155549431

Max Phase: Preclinical

Molecular Formula: C22H32O5

Molecular Weight: 376.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]12CCCC(C)(C)[C@@H]1CC(OC)c1cc(C(C)C)c(O)c(O)c12

Standard InChI:  InChI=1S/C22H32O5/c1-12(2)13-10-14-15(26-5)11-16-21(3,4)8-7-9-22(16,20(25)27-6)17(14)19(24)18(13)23/h10,12,15-16,23-24H,7-9,11H2,1-6H3/t15?,16-,22+/m0/s1

Standard InChI Key:  CBMYMGVEDZJJKH-MWVIVRMESA-N

Molfile:  

 
     RDKit          2D

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   16.3538  -15.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5660  -15.4099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3539  -14.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5700  -16.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2778  -16.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2786  -15.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0665  -14.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9864  -14.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9864  -13.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6904  -15.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4026  -14.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1107  -15.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4026  -13.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6975  -16.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9856  -16.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9856  -17.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6937  -17.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2778  -17.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5700  -17.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7780  -18.0250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8582  -17.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2688  -18.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4494  -18.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1504  -17.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1504  -16.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8582  -16.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 27 28  1  0
  5 28  1  0
 21  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538938

   ---

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: 376.49

Molecular Weight (Monoisotopic): 376.2250

AlogP: 4.55

#Rotatable Bonds: 3

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: 9.19

CX Basic pKa: ┄

CX LogP: 4.70

CX LogD: 4.69

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: 2.25

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