Ophiobolin Q

ID: ALA4550481

PubChem CID: 73386894

Max Phase: Preclinical

Molecular Formula: C25H36O4

Molecular Weight: 400.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)[C@H]2/C(C=O)=C\C[C@H]3[C@@H]([C@@H](C)/C=C\[C@H](O)C(C)(C)O)CC[C@]3(C)C[C@H]12

Standard InChI:  InChI=1S/C25H36O4/c1-15(6-9-22(28)24(3,4)29)18-10-11-25(5)13-19-16(2)12-21(27)23(19)17(14-26)7-8-20(18)25/h6-7,9,12,14-15,18-20,22-23,28-29H,8,10-11,13H2,1-5H3/b9-6-,17-7-/t15-,18+,19+,20-,22-,23-,25+/m0/s1

Standard InChI Key:  ZCYAUPOUCSSQGA-WBBAMFPJSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   44.1655  -18.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3772  -17.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5890  -18.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7956  -17.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6152  -19.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6152  -17.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7957  -19.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6214  -20.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4234  -20.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2270  -18.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2205  -18.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4447  -19.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1903  -18.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1895  -18.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9680  -19.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4501  -18.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9694  -17.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1992  -20.1367    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.1815  -19.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7773  -16.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3693  -16.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9934  -16.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4002  -17.2394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.4643  -17.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5153  -18.4487    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.7387  -18.7068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.7910  -20.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5435  -17.1940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   43.1832  -16.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5942  -17.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4113  -17.1217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.5864  -18.1181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3544  -16.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
 11  4  2  0
  7  5  1  0
  5 14  1  0
 13  6  1  0
  6  4  1  0
  7 10  1  0
 12  8  1  0
  8  9  2  0
  9  7  1  0
 10 11  1  0
 12 10  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  7 18  1  1
 14 19  1  1
 17 20  1  0
 20 21  1  0
 20 22  1  1
 13 23  1  6
 11 24  1  0
 10 25  1  6
 12 26  2  0
  9 27  1  0
 17 28  1  6
 21 29  2  0
 29 30  1  0
 30 31  1  6
 30  2  1  0
  2 32  1  0
 24 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4550481

   Ophiobolin Q

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: 400.56

Molecular Weight (Monoisotopic): 400.2614

AlogP: 4.02

#Rotatable Bonds: 5

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: 2.85

References

1. Cai R, Jiang H, Mo Y, Guo H, Li C, Long Y, Zang Z, She Z..  (2019)  Ophiobolin-Type Sesterterpenoids from the Mangrove Endophytic Fungus Aspergillus sp. ZJ-68.,  82  (8): [PMID:31365251] [10.1021/acs.jnatprod.9b00462]

Source

Source(1):

• Scientific Literature