(E)-(1R,3aS,9aR,10aS)-1-Hydroxy-7-((S)-3-hydroxy-1,4-dimtthyl-pent-3-enyl)-1,7,9a-trimethyl-3-oxo-1,2,3,3a,6,6a,7,8,9,aa,10,10a-dodecahydro-dicyclopenta[a,d]cyclooctene-4-carbaldehyde

ID: ALA522808

Chembl Id: CHEMBL522808

Cas Number: 4611-05-6

PubChem CID: 5281387

Product Number: sc-202266

Max Phase: Preclinical

Molecular Formula: C25H36O4

Molecular Weight: 400.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ophiobolin A | Ophiobolin A|4611-05-6|Cochliobolin A|Cochliobolin|Ophiobolin|CHEBI:7777|(1'R,2S,3S,3'S,4'R,5R,7'S,8'E,11'R)-4'-hydroxy-1',3,4'-trimethyl-5-(2-methylprop-1-enyl)-6'-oxospiro[oxolane-2,12'-tricyclo[9.3.0.03,7]tetradec-8-ene]-8'-carbaldehyde|NSC-114340|NSC 114340|CHEMBL522808|SCHEMBL1959293|DTXSID301017596|Ophiobolin A, >=95% (HPLC)|HY-N6781|HB0474|AKOS040742342|Ophiobola-7,19-dien-25-al, 14,18-epoxy-3-hydroxy-5-oxo-, (18R)-|LMPR0105050001|Spiro(dicyclopenta(a,d)cyclooctene-3(2H),2'Show More⌵

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

Standard InChI:  InChI=1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22+,23+,24+,25-/m0/s1

Standard InChI Key:  MWYYLZRWWNBROW-BDZRSQQBSA-N

Alternative Forms

1. Parent:

   

   ALA522808

   OPHIOBOLIN A

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

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: 4.41

#Rotatable Bonds: 2

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.34

CX Basic pKa:

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 0

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: 3.17

References

1. Fukushima Y, Sakagami Y, Marumo S.  (1993)  -Glucan biosynthesis inhibitors isolated from fungi as hyphal malformation inducer,  3  (6): [10.1016/S0960-894X(00)80319-4]

2. Shen X, Krasnoff SB, Lu SW, Dunbar CD, O'Neal J, Turgeon BG, Yoder OC, Gibson DM, Hamann MT..  (1999)  Characterization of 6-epi-3-anhydroophiobolin B from Cochliobolus heterostrophus.,  62  (6): [PMID:10395513] [10.1021/np980462e]

3. Li E, Clark AM, Rotella DP, Hufford CD..  (1995)  Microbial metabolites of ophiobolin A and antimicrobial evaluation of ophiobolins.,  58  (1): [PMID:7760080] [10.1021/np50115a009]

4. Duan G, Zhang Z, Zhang J, Zhou Y, Yu L, Yuan Q..  (2007)  Evaluation of crude toxin and metabolite produced by Helminthosporium gramineum Rabenh for the control of rice sheath blight in paddy fields,  26  (7): [10.1016/j.cropro.2006.09.014]

5. Evidente A, Andolfi A, Cimmino A, Vurro M, Fracchiolla M, Charudattan R..  (2006)  Herbicidal potential of ophiobolins produced by Drechslera gigantea.,  54  (5): [PMID:16506833] [10.1021/jf052843l]

6. Dasari R, Masi M, Lisy R, Ferdérin M, English LR, Cimmino A, Mathieu V, Brenner AJ, Kuhn JG, Whitten ST, Evidente A, Kiss R, Kornienko A..  (2015)  Fungal metabolite ophiobolin A as a promising anti-glioma agent: In vivo evaluation, structure-activity relationship and unique pyrrolylation of primary amines.,  25  (20): [PMID:26341136] [10.1016/j.bmcl.2015.08.066]

7. Masi M, Dasari R, Evidente A, Mathieu V, Kornienko A..  (2019)  Chemistry and biology of ophiobolin A and its congeners.,  29  (7): [PMID:30765189] [10.1016/j.bmcl.2019.02.007]

8. Zatout R,Masi M,Sangermano F,Vurro M,Zonno MC,Santoro E,Calabrò V,Superchi S,Evidente A.  (2020)  Drophiobiolins A and B, Bioactive Ophiobolan Sestertepenoids Produced by Dreschslera gigantea.,  83  (11): [PMID:33074690] [10.1021/acs.jnatprod.0c00836]

Source

Source(1):

• Scientific Literature