(3beta,5beta,14beta)-3,5,10,14-tetrahydroxy-19-norbufa-20,22-dienolide

ID: ALA4849730

PubChem CID: 164613318

Max Phase: Preclinical

Molecular Formula: C23H32O6

Molecular Weight: 404.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CC[C@]4(O)C[C@@H](O)CC[C@]34O)[C@@]1(O)CC[C@@H]2c1ccc(=O)oc1

Standard InChI:  InChI=1S/C23H32O6/c1-20-8-5-18-17(6-9-21(26)12-15(24)4-10-23(18,21)28)22(20,27)11-7-16(20)14-2-3-19(25)29-13-14/h2-3,13,15-18,24,26-28H,4-12H2,1H3/t15-,16+,17+,18-,20+,21-,22-,23-/m0/s1

Standard InChI Key:  YXIGJQVDQNPITF-DTDQOJBWSA-N

Molfile:  

 
     RDKit          2D

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    5.6951  -14.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6608  -14.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1825  -14.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4364  -13.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2412  -13.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7073  -16.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2808  -16.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5657  -15.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8521  -15.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551  -16.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5718  -16.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6914  -14.8745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9774  -16.1086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444  -16.9420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2717  -14.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  1  1
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  3 15  1  1
  4 16  1  1
 17 18  1  0
 17 20  1  0
 18 22  1  0
 21 19  1  0
 19 20  1  0
 21 22  1  0
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 24 25  1  0
 25 26  1  0
 17 27  1  1
 18 28  1  6
 25 29  1  1
 21 30  1  1
 22 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4849730

   ---

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: 404.50

Molecular Weight (Monoisotopic): 404.2199

AlogP: 2.08

#Rotatable Bonds: 1

Polar Surface Area: 111.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: ┄

CX LogP: 0.66

CX LogD: 0.66

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: 2.46

References

1. Zhou SW, Quan JY, Li ZW, Ye G, Shang Z, Chen ZP, Wang L, Li XY, Zhang XQ, Li J, Liu JS, Tian HY..  (2021)  Bufadienolides from the Eggs of the Toad Bufo bufo gargarizans and Their Antimelanoma Activities.,  84  (5.0): [PMID:33882233] [10.1021/acs.jnatprod.0c00840]

Source

Source(1):

• Scientific Literature