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

Associated Items:

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

Associated Targets(Human)

MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI/ADR-RES (33767 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF-10A (2462 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella aerogenes (4963 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ptbB Phosphotyrosine protein phosphatase (409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vibrio vulnificus (80 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vibrio parahaemolyticus (473 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vibrio anguillarum (183 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vibrio alginolyticus (165 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Edwardsiella tarda (165 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aeromonas hydrophila (292 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 368.56Molecular Weight (Monoisotopic): 368.2715AlogP: 5.65#Rotatable Bonds: 4
Polar Surface Area: 37.30Molecular Species: NEUTRALHBA: 2HBD: 1
#RO5 Violations: 1HBA (Lipinski): 2HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 5.20CX LogD: 5.20
Aromatic Rings: 0Heavy Atoms: 27QED Weighted: 0.51Np 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