(5alpha,6alpha)-epi-ophiobolin H

ID: ALA4440954

Chembl Id: CHEMBL4440954

PubChem CID: 53359835

Max Phase: Preclinical

Molecular Formula: C25H38O3

Molecular Weight: 386.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=C/C=C\[C@H](C)[C@H]1CC[C@]2(C)C[C@H]3[C@@H]4/C(=C\C[C@@H]12)CO[C@]4(O)C[C@@]3(C)O

Standard InChI:  InChI=1S/C25H38O3/c1-16(2)7-6-8-17(3)19-11-12-23(4)13-21-22-18(9-10-20(19)23)14-28-25(22,27)15-24(21,5)26/h6-9,17,19-22,26-27H,10-15H2,1-5H3/b8-6-,18-9-/t17-,19+,20-,21-,22-,23+,24+,25+/m0/s1

Standard InChI Key:  IBUCSLMTZXQXRS-AUSKLCKPSA-N

Alternative Forms

1. Parent:

   

   ALA4440954

   (1S,3R,6R,7S,9E,13R,15R,16R)-3,15-dimethyl-6-[(2S,3Z)-6-methylhepta-3,5-dien-2-yl]-12-oxatetracyclo[8.5.1.03,7.013,16]hexadec-9-ene-13,15-diol

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: 386.58

Molecular Weight (Monoisotopic): 386.2821

AlogP: 5.00

#Rotatable Bonds: 3

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.66

CX Basic pKa:

CX LogP: 4.54

CX LogD: 4.54

Aromatic Rings: 0

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: 3.00

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]

2. Chi LP,Li XM,Wan YP,Li X,Wang BG.  (2020)  Ophiobolin Sesterterpenoids and Farnesylated Phthalide Derivatives from the Deep Sea Cold-Seep-Derived Fungus Aspergillus insuetus SD-512.,  83  (12): [PMID:33322904] [10.1021/acs.jnatprod.0c00860]

Source

Source(1):

• Scientific Literature