coumermycin A1

ID: ALA389471

Chembl Id: CHEMBL389471

PubChem CID: 54697785

Max Phase: Preclinical

Molecular Formula: C55H59N5O20

Molecular Weight: 1110.09

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Coumermycin A1 | Coumamycin|Notomycin A1|CHEMBL389471|BDBM50048490|DB13912

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

Alternative Forms

1. Parent:

   

   ALA389471

   COUMERMYCIN A1

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

Calculated 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