ID: ALA389471

Max Phase: Preclinical

Molecular Formula: C55H59N5O20

Molecular Weight: 1110.09

Molecule Type: Small molecule

Representations

Synonyms (1): Coumermycin A1
Synonyms from Alternative Forms(1):

Canonical SMILES:  CO[C@H]1[C@H](OC(=O)c2ccc(C)[nH]2)[C@H](O)[C@@H](Oc2ccc3c(O)c(NC(=O)c4c[nH]c(C(=O)Nc5c(O)c6ccc(O[C@H]7OC(C)(C)[C@@H](OC)[C@H](OC(=O)c8ccc(C)[nH]8)[C@@H]7O)c(C)c6oc5=O)c4C)c(=O)oc3c2C)OC1(C)C

Standard InChI:  InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m0/s1

Standard InChI Key:  WTIJXIZOODAMJT-IYKSDEDASA-N

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

Properties

Molecular Weight: 1110.09

Molecular Weight (Monoisotopic): 1109.3753

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Hadden MK, Blagg BS..  (2007)  Cytotoxic small molecule dimers and their inhibitory activity against human breast cancer cells.,  17  (18): [PMID:17656092] [10.1016/j.bmcl.2007.07.014]

2. Zhao H, Donnelly AC, Kusuma BR, Brandt GE, Brown D, Rajewski RA, Vielhauer G, Holzbeierlein J, Cohen MS, Blagg BS..  (2011)  Engineering an antibiotic to fight cancer: optimization of the novobiocin scaffold to produce anti-proliferative agents.,  54  (11): [PMID:21553822] [10.1021/jm200148p]

3. Davenport J, Manjarrez JR, Peterson L, Krumm B, Blagg BS, Matts RL..  (2011)  Gambogic acid, a natural product inhibitor of Hsp90.,  74  (5): [PMID:21486005] [10.1021/np200029q]

4. Kusuma BR, Peterson LB, Zhao H, Vielhauer G, Holzbeierlein J, Blagg BS..  (2011)  Targeting the heat shock protein 90 dimer with dimeric inhibitors.,  54  (18): [PMID:21861487] [10.1021/jm200553w]

5. 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]

6. Singh SB, Goetz MA, Smith SK, Zink DL, Polishook J, Onishi R, Salowe S, Wiltsie J, Allocco J, Sigmund J, Dorso K, de la Cruz M, Martín J, Vicente F, Genilloud O, Donald RG, Phillips JW..  (2012)  Kibdelomycin A, a congener of kibdelomycin, derivatives and their antibacterial activities.,  22  (23): [PMID:23084277] [10.1016/j.bmcl.2012.09.071]

7. McConnell JR, Alexander LA, McAlpine SR..  (2014)  A heat shock protein 90 inhibitor that modulates the immunophilins and regulates hormone receptors without inducing the heat shock response.,  24  (2): [PMID:24360559] [10.1016/j.bmcl.2013.11.059]

8. Gavenonis J, Jonas NE, Kritzer JA..  (2014)  Potential C-terminal-domain inhibitors of heat shock protein 90 derived from a C-terminal peptide helix.,  22  (15): [PMID:24984936] [10.1016/j.bmc.2014.06.006]

Source

Source(1):

• Scientific Literature