3-(2-Nitro-phenyl)-propionic acid 2-((4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-hydroxy-4a,6a-dimethyl-2-oxo-8-propyl-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-7,9-dioxa-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester

ID: ALA2335077

PubChem CID: 71567382

Max Phase: Preclinical

Molecular Formula: C34H41NO9

Molecular Weight: 607.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)COC(=O)CCc2ccccc2[N+](=O)[O-])O1

Standard InChI:  InChI=1S/C34H41NO9/c1-4-7-30-43-28-17-24-23-12-11-21-16-22(36)14-15-32(21,2)31(23)26(37)18-33(24,3)34(28,44-30)27(38)19-42-29(39)13-10-20-8-5-6-9-25(20)35(40)41/h5-6,8-9,14-16,23-24,26,28,30-31,37H,4,7,10-13,17-19H2,1-3H3/t23-,24-,26-,28+,30?,31+,32-,33-,34+/m0/s1

Standard InChI Key:  JQAAKPIEPMWBTQ-VKXGYDRBSA-N

Molfile:  

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M  CHG  2  40   1  42  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2335077

   [2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-9,13-dimethyl-16-oxo-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-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: 607.70

Molecular Weight (Monoisotopic): 607.2781

AlogP: 4.81

#Rotatable Bonds: 9

Polar Surface Area: 142.27

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.39

CX LogD: 5.39

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.24

Np Likeness Score: 1.32

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