3-anhydro-6-hydroxy-ophiobolin A

ID: ALA2393051

Chembl Id: CHEMBL2393051

PubChem CID: 71655010

Max Phase: Preclinical

Molecular Formula: C25H34O4

Molecular Weight: 398.54

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

Standard InChI:  InChI=1S/C25H34O4/c1-15(2)10-19-12-17(4)24(29-19)9-8-23(5)13-20-16(3)11-22(27)25(20,28)18(14-26)6-7-21(23)24/h6,10-11,14,17,19-21,28H,7-9,12-13H2,1-5H3/b18-6-/t17-,19-,20+,21+,23+,24-,25-/m0/s1

Standard InChI Key:  MNTJKNWRCITJMY-JCBJYGFASA-N

Alternative Forms

1. Parent:

   

   ALA2393051

   3-anhydro-6-hydroxy-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: 398.54

Molecular Weight (Monoisotopic): 398.2457

AlogP: 4.33

#Rotatable Bonds: 2

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.05

CX Basic pKa: ┄

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: 3.14

References

1. 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]

2. Xue D, Wang Q, Chen Z, Cai L, Bao L, Qi Q, Liu L, Wang X, Jin H, Wang J, Wu H, Liu H, Chen Q..  (2015)  3-Anhydro-6-hydroxy-ophiobolin A, a fungal sesterterpene from Bipolaris oryzae induced autophagy and promoted the degradation of α-synuclein in PC12 cells.,  25  (7): [PMID:25748161] [10.1016/j.bmcl.2015.02.030]

Source

Source(1):

• Scientific Literature