4-Acetoxydolastane

ID: ALA5290964

Max Phase: Preclinical

Molecular Formula: C21H32O4

Molecular Weight: 348.48

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H](OC(C)=O)[C@H]2CC=C3[C@](C)(CC[C@]3(O)C(C)C)C[C@]12O

Standard InChI:  InChI=1S/C21H32O4/c1-13(2)20(23)11-10-19(5)12-21(24)14(3)6-8-17(25-15(4)22)16(21)7-9-18(19)20/h9,13,16-17,23-24H,3,6-8,10-12H2,1-2,4-5H3/t16-,17-,19-,20+,21+/m1/s1

Standard InChI Key:  XOWFFSZGRWKZLS-LPOYBJAFSA-N

Molfile:  

 
     RDKit          2D

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   -1.2739    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6318   -0.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1656   -0.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207    0.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1650    1.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6318    1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724    1.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4726    1.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3228    0.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9060    0.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7028    0.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926   -0.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1107    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1650    2.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2740   -1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2740   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596    0.6185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    1.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  1  0
  5  4  2  0
  6  5  1  0
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  2 16  1  0
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  1 19  1  0
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 22 24  2  0
  2 25  1  1
  1 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5290964

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 348.48

Molecular Weight (Monoisotopic): 348.2301

AlogP: 3.52

#Rotatable Bonds: 2

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 2.45

CX LogD: 2.45

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: 2.56

References

1. Cockram PE, Smith TK..  (2018)  Active Natural Product Scaffolds against Trypanosomatid Parasites: A Review.,  81  (9): [PMID:30234295] [10.1021/acs.jnatprod.8b00159]

Source

Source(1):

• Scientific Literature