5-Benzyl-8,8-dimethyl-11-(6-oxiranyl-6-oxo-hexyl)-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (chlamydocin)

ID: ALA2371450

Chembl Id: CHEMBL2371450

PubChem CID: 73356211

Max Phase: Preclinical

Molecular Formula: C28H38N4O6

Molecular Weight: 526.63

Molecule Type: Protein

Names and Identifiers

Synonyms: Chlamydocin | chlamydocin|CHEMBL2371450|SGYJGGKDGBXCNY-NNXSRULWSA-N

Canonical SMILES:  CC1(C)NC(=O)[C@H](CCCCCC(=O)[C@H]2CO2)NC(=O)[C@H]2CCCN2C(=O)[C@H](Cc2ccccc2)NC1=O

Standard InChI:  InChI=1S/C28H38N4O6/c1-28(2)27(37)30-20(16-18-10-5-3-6-11-18)26(36)32-15-9-13-21(32)25(35)29-19(24(34)31-28)12-7-4-8-14-22(33)23-17-38-23/h3,5-6,10-11,19-21,23H,4,7-9,12-17H2,1-2H3,(H,29,35)(H,30,37)(H,31,34)/t19-,20-,21+,23+/m0/s1

Standard InChI Key:  SGYJGGKDGBXCNY-NNXSRULWSA-N

Alternative Forms

1. Parent:

   

   ALA2371450

   CHLAMYDOCIN

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 526.63

Molecular Weight (Monoisotopic): 526.2791

AlogP: 1.02

#Rotatable Bonds: 9

Polar Surface Area: 137.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.72

CX Basic pKa:

CX LogP: 1.39

CX LogD: 1.39

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.32

Np Likeness Score: 0.84

References

1. Shute RE, Dunlap B, Rich DH..  (1987)  Analogues of the cytostatic and antimitogenic agents chlamydocin and HC-toxin: synthesis and biological activity of chloromethyl ketone and diazomethyl ketone functionalized cyclic tetrapeptides.,  30  (1): [PMID:3806605] [10.1021/jm00384a013]

2. Hoque MA, Arai T, Nishino N, Kim HJ, Ito A, Yoshida M..  (2012)  Cyclic tetrapeptides with thioacetate tails or intramolecular disulfide bridge as potent inhibitors of histone deacetylases.,  22  (21): [PMID:23021104] [10.1016/j.bmcl.2012.03.004]

3. Du L, Risinger AL, King JB, Powell DR, Cichewicz RH..  (2014)  A potent HDAC inhibitor, 1-alaninechlamydocin, from a Tolypocladium sp. induces G2/M cell cycle arrest and apoptosis in MIA PaCa-2 cells.,  77  (7): [PMID:24999749] [10.1021/np500387h]

Source

Source(1):

• Scientific Literature