2-((8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl 3-(2-nitrophenyl)propanoate

ID: ALA2335079

PubChem CID: 71567256

Max Phase: Preclinical

Molecular Formula: C30H35NO8

Molecular Weight: 537.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)COC(=O)CCc1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C30H35NO8/c1-28-13-11-20(32)15-19(28)8-9-21-22-12-14-30(36,29(22,2)16-24(33)27(21)28)25(34)17-39-26(35)10-7-18-5-3-4-6-23(18)31(37)38/h3-6,11,13,15,21-22,24,27,33,36H,7-10,12,14,16-17H2,1-2H3/t21-,22-,24-,27+,28-,29-,30-/m0/s1

Standard InChI Key:  INGCNJBREBHSPB-QYPWACJRSA-N

Molfile:  

     RDKit          2D

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  4 28  1  1
  6 29  1  6
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M  CHG  2  40   1  42  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2335079

   [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 3-(2-nitrophenyl)propanoate

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: 537.61

Molecular Weight (Monoisotopic): 537.2363

AlogP: 3.65

#Rotatable Bonds: 7

Polar Surface Area: 144.04

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.61

CX Basic pKa: ┄

CX LogP: 3.93

CX LogD: 3.93

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.30

Np Likeness Score: 1.22

References

1. Marquez Ruiz JF, Kedziora K, Pigott M, Keogh B, Windle H, Gavin J, Kelleher DP, Gilmer JF..  (2013)  A nitrophenyl-based prodrug type for colorectal targeting of prednisolone, budesonide and celecoxib.,  23  (6): [PMID:23416011] [10.1016/j.bmcl.2013.01.060]

Source

Source(1):

• Scientific Literature