(6beta,9beta,13alpha,14beta,17beta,18beta,20alpha)-2,3-dihydroxy-9,13-dimethyl-6-(nitromethyl)-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid

ID: ALA4463133

PubChem CID: 118408869

Max Phase: Preclinical

Molecular Formula: C30H41NO6

Molecular Weight: 511.66

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(O)c(O)cc2c1[C@H](C[N+](=O)[O-])C=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@](C)(C(=O)O)CC[C@]3(C)CC[C@]12C

Standard InChI:  InChI=1S/C30H41NO6/c1-17-23-18(16-31(36)37)13-21-28(4,19(23)14-20(32)24(17)33)10-12-30(6)22-15-27(3,25(34)35)8-7-26(22,2)9-11-29(21,30)5/h13-14,18,22,32-33H,7-12,15-16H2,1-6H3,(H,34,35)/t18-,22+,26+,27+,28-,29+,30-/m0/s1

Standard InChI Key:  PWMPMLPFFOITIJ-NVHHSDGASA-N

Molfile:  

 
     RDKit          2D

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    2.9805   -6.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9615   -4.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6983   -8.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -7.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659   -5.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5345   -3.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5304   -6.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3979   -5.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2398   -5.1613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6712   -5.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9636   -1.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2021   -2.3765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258   -8.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8422   -8.4631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5595   -8.0497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
  2  3  1  6
  4  5  1  0
  5  6  2  0
  6  9  1  0
  8  7  1  0
  7  4  2  0
  8  9  2  0
  9 10  1  0
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 20 24  1  0
 21 22  1  0
 22 23  1  0
 23  2  1  0
  2 24  1  0
  6 25  1  0
  5 26  1  0
  4 27  1  0
 16 28  1  6
 17 29  1  1
 12 30  1  1
 20 31  1  1
 21 32  1  1
  3 33  2  0
  3 34  1  0
 10 35  1  1
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 36 37  2  0
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M  CHG  2  36   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4463133

   (2R,4aS,6aR,6aS,8R,14aS,14bR)-10,11-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-8-(nitromethyl)-3,4,5,6,8,13,14,14b-octahydro-1H-picene-2-carboxylic acid

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: 511.66

Molecular Weight (Monoisotopic): 511.2934

AlogP: 6.46

#Rotatable Bonds: 3

Polar Surface Area: 120.90

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.64

CX Basic pKa: ┄

CX LogP: 6.38

CX LogD: 3.68

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.19

Np Likeness Score: 2.27

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