3-anhydro-6-epi-ophiobolin A

ID: ALA2393053

Cas Number: 90411-20-4

PubChem CID: 12306828

Product Number: A329324, Order Now?

Max Phase: Preclinical

Molecular Formula: C25H34O3

Molecular Weight: 382.54

Molecule Type: Small molecule

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)[C@H]4/C(C=O)=C\C[C@H]32)O1

Standard InChI:  InChI=1S/C25H34O3/c1-15(2)10-19-12-17(4)25(28-19)9-8-24(5)13-20-16(3)11-21(27)23(20)18(14-26)6-7-22(24)25/h6,10-11,14,17,19-20,22-23H,7-9,12-13H2,1-5H3/b18-6-/t17-,19-,20+,22+,23-,24+,25-/m0/s1

Standard InChI Key:  MDYSLOGZXCWLSL-MUKMEUIDSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   23.8746   -3.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6704   -2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7104   -2.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9391   -1.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4227   -2.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2924   -5.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3503   -4.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4796   -5.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0896   -3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6763   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5008   -2.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0891   -4.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6747   -4.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4995   -4.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0867   -3.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0825   -4.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8660   -4.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3543   -3.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6159   -4.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3276   -3.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2206   -2.2405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0745   -5.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3703   -3.7832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.0828   -5.4957    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.5988   -2.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4005   -1.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1370   -2.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8271   -1.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1835   -2.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2828   -3.5874    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.6616   -6.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6
  3  2  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6 13  1  0
 12  7  1  0
  7  8  1  0
  8  6  2  0
  9 10  2  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 15 11  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  1  1  0
  1 15  1  0
  7 19  2  0
  9 20  1  0
 20 21  2  0
 16 22  1  1
 12 23  1  6
 13 24  1  1
  5 25  1  1
  3 26  1  6
 26 27  2  0
 27 28  1  0
 27 29  1  0
 15 30  1  6
  6 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2393053

   Anhydroepiophiobolin 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: 382.54

Molecular Weight (Monoisotopic): 382.2508

AlogP: 5.21

#Rotatable Bonds: 2

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.65

CX LogD: 4.65

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: 3.33

References

1. 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]

2. Wang QX, Yang JL, Qi QY, Bao L, Yang XL, Liu MM, Huang P, Zhang LX, Chen JL, Cai L, Liu HW..  (2013)  3-Anhydro-6-hydroxy-ophiobolin A, a new sesterterpene inhibiting the growth of methicillin-resistant Staphylococcus aureus and inducing the cell death by apoptosis on K562, from the phytopathogenic fungus Bipolaris oryzae.,  23  (12): [PMID:23668986] [10.1016/j.bmcl.2013.04.034]

3. 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]

4. 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