(Z)-6-[(2R,5R,8R,11R,12S)-8-(4-Hydroxy-benzyl)-2-isopropyl-5,12-dimethyl-3,6,9,13-tetraoxo-1,4,7,10tetraaza-cyclotridec-11-yl]-hex-4-enoic acid

ID: ALA257972

Chembl Id: CHEMBL257972

PubChem CID: 16095114

Max Phase: Preclinical

Molecular Formula: C27H38N4O7

Molecular Weight: 530.62

Molecule Type: Small molecule

Names and Identifiers

Synonyms: azumamide C | AZUMAMIDE C|CHEMBL257972|BDBM50377384

Canonical SMILES:  CC(C)[C@H]1NC(=O)[C@@H](C)[C@@H](C/C=C\CCC(=O)O)NC(=O)[C@@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC1=O

Standard InChI:  InChI=1S/C27H38N4O7/c1-15(2)23-27(38)28-17(4)25(36)30-21(14-18-10-12-19(32)13-11-18)26(37)29-20(16(3)24(35)31-23)8-6-5-7-9-22(33)34/h5-6,10-13,15-17,20-21,23,32H,7-9,14H2,1-4H3,(H,28,38)(H,29,37)(H,30,36)(H,31,35)(H,33,34)/b6-5-/t16-,17+,20+,21+,23+/m0/s1

Standard InChI Key:  QKNOLJBQLJGNKI-LFUPQXEOSA-N

Alternative Forms

1. Parent:

   

   ALA257972

   AZUMAMIDE C

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: 530.62

Molecular Weight (Monoisotopic): 530.2740

AlogP: 1.01

#Rotatable Bonds: 8

Polar Surface Area: 173.93

Molecular Species: ACID

HBA: 6

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.24

CX Basic pKa:

CX LogP: 1.34

CX LogD: -1.67

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.27

Np Likeness Score: 1.78

References

1. Nakao Y, Narazaki G, Hoshino T, Maeda S, Yoshida M, Maejima H, Yamashita JK..  (2008)  Evaluation of antiangiogenic activity of azumamides by the in vitro vascular organization model using mouse induced pluripotent stem (iPS) cells.,  18  (9): [PMID:18397826] [10.1016/j.bmcl.2008.03.053]

2. Villadsen JS, Stephansen HM, Maolanon AR, Harris P, Olsen CA..  (2013)  Total synthesis and full histone deacetylase inhibitory profiling of Azumamides A-E as well as β²- epi-Azumamide E and β³-epi-Azumamide E.,  56  (16): [PMID:23865683] [10.1021/jm4008449]

3. Maolanon AR, Villadsen JS, Christensen NJ, Hoeck C, Friis T, Harris P, Gotfredsen CH, Fristrup P, Olsen CA..  (2014)  Methyl effect in azumamides provides insight into histone deacetylase inhibition by macrocycles.,  57  (22): [PMID:25380299] [10.1021/jm501399d]

4. Villadsen JS, Kitir B, Wich K, Friis T, Madsen AS, Olsen CA.  (2014)  An azumamide C analogue without the zinc-binding functionality,  5  (12): [10.1039/C4MD00252K]

Source

Source(1):

• Scientific Literature