(1S,4aR,6R,6aR,9S,11aS,11bR,12R)-6,12-dihydroxy-4,4,11b-trimethyl-8-methylene-7-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalen-1-yl acetate

ID: ALA5286538

Max Phase: Preclinical

Molecular Formula: C22H32O5

Molecular Weight: 376.49

Names and Identifiers

Canonical SMILES:  C=C1C(=O)[C@@]23[C@H](O)C[C@@H]4C(C)(C)CC[C@H](OC(C)=O)[C@@]4(C)[C@@H]2CC[C@@H]1[C@H]3O

Standard InChI:  InChI=1S/C22H32O5/c1-11-13-6-7-14-21(5)15(10-16(24)22(14,18(11)25)19(13)26)20(3,4)9-8-17(21)27-12(2)23/h13-17,19,24,26H,1,6-10H2,2-5H3/t13-,14-,15+,16+,17-,19+,21-,22-/m0/s1

Standard InChI Key:  LTQYOOFDGCXQJJ-OACISFLYSA-N

Molfile:  

 
     RDKit          2D

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    1.3708    0.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7514   -1.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4561    0.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6579   -1.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750    0.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627   -0.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798    0.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8668    0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674   -0.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1609   -1.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7556   -1.8946    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8766   -2.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4561    0.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    0.5616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674   -1.0786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -1.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824    1.3608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615    1.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615    2.1913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8668    0.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 10  1  0
 10 11  2  0
  2 12  1  1
  8 13  1  0
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  5 15  1  0
 15 16  1  0
 16 17  1  0
 17  4  1  0
  4 18  1  0
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  3 19  1  6
  4 20  1  1
 17 21  1  0
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  5 23  1  6
  6 24  1  1
  9 25  2  0
  7 26  1  6
  8 27  1  6
 23 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286538

   ---

Molecule Features

Natural Product: Yes

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: 376.49

Molecular Weight (Monoisotopic): 376.2250

AlogP: 2.64

#Rotatable Bonds: 1

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.95

CX Basic pKa: ┄

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: 3.50

References

1. Aoyagi Y, Tomita K, Kobayashi A, Nakamura A, Fujii Y, Yagi M, Ichimaru Y, Ozawa K, Park HS, Fukaya H, Yano R, Hasuda T, Takeya K, Hitotsuyanagi Y, Gui MY, Jin YR, Li XW..  (2023)  Synthesis of 1-O-acyl- and 1-oxo-kamebanin analogues and their cytotoxic activity.,  82  [PMID:36690039] [10.1016/j.bmcl.2023.129149]

Source

Source(1):

• Scientific Literature