(9beta,13alpha,14beta,17beta,18beta,20alpha)-3-hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oyl-fluoride

ID: ALA4459092

PubChem CID: 138623559

Max Phase: Preclinical

Molecular Formula: C29H37FO3

Molecular Weight: 452.61

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=C(O)C(=O)C=C2C1=CC=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@](C)(C(=O)F)CC[C@]3(C)CC[C@]12C

Standard InChI:  InChI=1S/C29H37FO3/c1-17-18-7-8-21-27(4,19(18)15-20(31)23(17)32)12-14-29(6)22-16-26(3,24(30)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,32H,9-14,16H2,1-6H3/t22-,25-,26-,27+,28-,29+/m1/s1

Standard InChI Key:  COVSAPDFNJBGKH-JJWQIEBTSA-N

Molfile:  

 
     RDKit          2D

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   19.1950   -2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6139   -3.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0245   -2.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0603   -6.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7725   -7.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4885   -6.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.7600   -4.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8958   -3.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3468   -8.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9132   -7.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9146   -5.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1827   -4.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1786   -6.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0504   -5.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8880   -5.2645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.3192   -5.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6116   -1.7724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8500   -2.4841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  2 24  1  0
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 12 30  1  1
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  3 33  2  0
  3 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4459092

   ---

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: 452.61

Molecular Weight (Monoisotopic): 452.2727

AlogP: 7.11

#Rotatable Bonds: 1

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.75

CX Basic pKa: ┄

CX LogP: 5.58

CX LogD: 5.57

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: 2.99

References

1. Chen Z, Zhang D, Yan S, Hu C, Huang Z, Li Z, Peng S, Li X, Zhu Y, Yu H, Lian B, Kang Q, Li M, Zeng Z, Zhang XK, Su Y..  (2019)  SAR study of celastrol analogs targeting Nur77-mediated inflammatory pathway.,  177  [PMID:31132532] [10.1016/j.ejmech.2019.05.009]

2. Zhan, Yanyan Y and 22 more authors.  2008-09  Cytosporone B is an agonist for nuclear orphan receptor Nur77.  [PMID:18690216]

Source

Source(1):

• Scientific Literature