(1S,4aS,10aR)-methyl 5,6-dihydroxy-8-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate

ID: ALA4277509

PubChem CID: 145984612

Max Phase: Preclinical

Molecular Formula: C21H30O4

Molecular Weight: 346.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@]1(C)CCC[C@]2(C)c3c(O)c(O)cc(C(C)C)c3CC[C@@H]12

Standard InChI:  InChI=1S/C21H30O4/c1-12(2)14-11-15(22)18(23)17-13(14)7-8-16-20(17,3)9-6-10-21(16,4)19(24)25-5/h11-12,16,22-23H,6-10H2,1-5H3/t16-,20+,21+/m1/s1

Standard InChI Key:  NPNOFWVCLCUXQM-CZAAIQMYSA-N

Molfile:  

     RDKit          2D

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   20.6815  -13.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2771  -12.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8681  -13.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5754  -11.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5754  -12.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2807  -10.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9860  -11.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9825  -12.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6846  -12.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3946  -12.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6915  -10.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3938  -11.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1013  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1077  -10.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4007   -9.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6961  -10.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4038   -8.8363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8058  -11.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9787  -10.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9746  -12.9058    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.2744  -13.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0509  -13.1978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8636  -14.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7994  -12.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5167  -10.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9903   -9.6452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 15 17  1  0
 13 18  1  0
  7 19  1  1
  8 20  1  6
  2  1  1  0
  2  3  1  1
  3 21  1  0
  3 22  2  0
 21 23  1  0
 18 24  1  0
 18 25  1  0
 16 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4277509

   ---

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: 346.47

Molecular Weight (Monoisotopic): 346.2144

AlogP: 4.40

#Rotatable Bonds: 2

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 5.28

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: 2.11

References

1. Mahdjour S, Guardia JJ, Rodríguez-Serrano F, Garrido JM, López-Barajas IB, Mut-Salud N, Chahboun R, Alvarez-Manzaneda E..  (2018)  Synthesis and antiproliferative activity of podocarpane and totarane derivatives.,  158  [PMID:30248657] [10.1016/j.ejmech.2018.09.051]

Source

Source(1):

• Scientific Literature