12alpha-Bromo-3-hydroxyiminoolean-28beta-13betaolide

ID: ALA2237349

PubChem CID: 76326237

Max Phase: Preclinical

Molecular Formula: C30H46BrNO3

Molecular Weight: 548.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC[C@@]23CC[C@]4(C)[C@@](OC2=O)([C@@H]3C1)[C@@H](Br)C[C@@H]1[C@@]2(C)CC/C(=N\O)C(C)(C)[C@@H]2CC[C@]14C

Standard InChI:  InChI=1S/C30H46BrNO3/c1-24(2)12-14-29-15-13-28(7)27(6)11-8-18-25(3,4)22(32-34)9-10-26(18,5)19(27)16-21(31)30(28,20(29)17-24)35-23(29)33/h18-21,34H,8-17H2,1-7H3/b32-22+/t18-,19+,20+,21-,26-,27+,28-,29-,30+/m0/s1

Standard InChI Key:  JSTHQUISSXLUCL-MIIGWKSKSA-N

Molfile:  

     RDKit          2D

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    8.9212   -9.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9428   -8.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5257   -8.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6679  -10.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7810  -11.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571  -12.4686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1102   -8.8033    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.7975   -9.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2008   -9.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7085   -8.9602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492  -12.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  8 30  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA2237349

   (1S,4S,5R,8R,10E,13R,14R,16S,17S,18R)-16-bromo-10-hydroxyimino-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-23-one

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: 548.61

Molecular Weight (Monoisotopic): 547.2661

AlogP: 7.75

#Rotatable Bonds: ┄

Polar Surface Area: 58.89

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.10

CX Basic pKa: 1.95

CX LogP: 7.62

CX LogD: 7.62

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.15

Np Likeness Score: 2.74

References

1. Kaminskyy D, Bednarczyk-Cwynar B, Vasylenko O, Kazakova O, Zimenkovsky B, Zaprutko L, Lesyk R.  (2012)  Synthesis of new potential anticancer agents based on 4-thiazolidinone and oleanane scaffolds,  21  (11): [10.1007/s00044-011-9893-9]

2. Salvador JAR, Leal AS, Valdeira AS, Gonçalves BMF, Alho DPS, Figueiredo SAC, Silvestre SM, Mendes VIS..  (2017)  Oleanane-, ursane-, and quinone methide friedelane-type triterpenoid derivatives: Recent advances in cancer treatment.,  142  [PMID:28754470] [10.1016/j.ejmech.2017.07.013]

Source

Source(1):

• Scientific Literature