21,21-O-dihydro-6-epi-ophiobolin G

ID: ALA4170611

Chembl Id: CHEMBL4170611

PubChem CID: 53359838

Max Phase: Preclinical

Molecular Formula: C25H36O2

Molecular Weight: 368.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H36O2/c1-16(2)7-6-8-17(3)20-11-12-25(5)14-21-18(4)13-23(27)24(21)19(15-26)9-10-22(20)25/h6-9,13,17,20-22,24,26H,10-12,14-15H2,1-5H3/b8-6-,19-9-/t17-,20+,21+,22-,24-,25+/m0/s1

Standard InChI Key:  GUXDHNIKRQCWIE-ZDZUEPJSSA-N

Alternative Forms

1. Parent:

   

   ALA4170611

   (1R,3S,7R,8E,11S,12R)-8-(hydroxymethyl)-1,4-dimethyl-12-[(2S,3Z)-6-methylhepta-3,5-dien-2-yl]tricyclo[9.3.0.03,7]tetradeca-4,8-dien-6-one

Molecule Features

Natural Product: No

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: 368.56

Molecular Weight (Monoisotopic): 368.2715

AlogP: 5.65

#Rotatable Bonds: 4

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 5.20

CX LogD: 5.20

Aromatic Rings: 0

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: 3.12

References

1. Zhu T, Lu Z, Fan J, Wang L, Zhu G, Wang Y, Li X, Hong K, Piyachaturawat P, Chairoungdua A, Zhu W..  (2018)  Ophiobolins from the Mangrove Fungus Aspergillus ustus.,  81  (1): [PMID:29286660] [10.1021/acs.jnatprod.7b00335]

2. 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]

3. 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