Oligomycin A

ID: ALA1256136

Chembl Id: CHEMBL1256136

PubChem CID: 52947560

Max Phase: Preclinical

Molecular Formula: C45H74O11

Molecular Weight: 791.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H]1/C=C/C=C/C[C@H](C)[C@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)/C=C/C(=O)O[C@H]2[C@@H](C)[C@@H](CC1)O[C@@]1(CC[C@@H](C)[C@@H](C[C@H](C)O)O1)[C@@H]2C

Standard InChI:  InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42+,44+,45-/m1/s1

Standard InChI Key:  MNULEGDCPYONBU-BOXGPLBDSA-N

Alternative Forms

1. Parent:

   

   ALA1256136

   OLIGOMYCIN A

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: 791.08

Molecular Weight (Monoisotopic): 790.5231

AlogP: 5.88

#Rotatable Bonds: 3

Polar Surface Area: 180.05

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.29

CX Basic pKa: ┄

CX LogP: 7.45

CX LogD: 7.45

Aromatic Rings: ┄

Heavy Atoms: 56

QED Weighted: 0.22

Np Likeness Score: 2.09

References

1. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

2. Sato S, Iwata F, Yamada S, Katayama M..  (2012)  Neomaclafungins A-I: oligomycin-class macrolides from a marine-derived actinomycete.,  75  (11): [PMID:23102410] [10.1021/np300719g]

3. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

4. Lysenkova LN, Turchin KF, Korolev AM, Dezhenkova LG, Bekker OB, Shtil AA, Danilenko VN, Preobrazhenskaya MN..  (2013)  Synthesis and cytotoxicity of oligomycin A derivatives modified in the side chain.,  21  (11): [PMID:23623676] [10.1016/j.bmc.2013.03.081]

Source

Source(1):

• Scientific Literature