8-epi-Ophiobolin J

ID: ALA4574086

PubChem CID: 101419604

Max Phase: Preclinical

Molecular Formula: C25H36O4

Molecular Weight: 400.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=C[C@H]1C[C@H](C)[C@]2(CC[C@]3(C)C[C@@H]4C(C)=CC(=O)/C4=C(\CO)[C@H](O)C[C@H]32)O1

Standard InChI:  InChI=1S/C25H36O4/c1-14(2)8-17-10-16(4)25(29-17)7-6-24(5)12-18-15(3)9-21(28)23(18)19(13-26)20(27)11-22(24)25/h8-9,16-18,20,22,26-27H,6-7,10-13H2,1-5H3/b23-19+/t16-,17-,18+,20+,22+,24+,25-/m0/s1

Standard InChI Key:  LFYREHKMIHWZQF-VNBBXFQNSA-N

Molfile:  

 
     RDKit          2D

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   19.2579   -2.9127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2974   -2.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.7159   -3.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2951   -2.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1148   -4.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1148   -2.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6899   -3.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9610   -3.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3126   -3.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2952   -4.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9889   -4.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.2989   -6.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2598   -4.2031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6810   -5.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8721   -5.3530    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2057   -2.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9810   -1.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2671   -3.9580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7106   -2.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3942   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7566   -2.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9824   -2.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6
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  3  4  1  0
  4  5  1  0
  5  1  1  0
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  6  7  1  0
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 12 13  1  0
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  1 10  1  0
  6 14  1  0
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 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 20 21  1  0
 18 22  2  0
 11 23  1  1
 16 24  1  1
  5 25  1  1
  3 26  1  6
 10 27  1  6
 26 28  2  0
 28 29  1  0
 28 30  1  0
  7 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4574086

   8-epi-ophiobolin J

Molecule Features

Natural Product: Yes

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: 400.56

Molecular Weight (Monoisotopic): 400.2614

AlogP: 4.12

#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: ┄

CX Basic pKa: ┄

CX LogP: 3.32

CX LogD: 3.32

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: 2.87

References

1. Liu M, Sun W, Shen L, Hao X, Al Anbari WH, Lin S, Li H, Gao W, Wang J, Hu Z, Zhang Y..  (2019)  Bipolaricins A-I, Ophiobolin-Type Tetracyclic Sesterterpenes from a Phytopathogenic Bipolaris sp. Fungus.,  82  (10): [PMID:31573805] [10.1021/acs.jnatprod.9b00744]

Source

Source(1):

• Scientific Literature