{3-[(6S,9S,12S,14aR)-6-sec-Butyl-5,8,11,14-tetraoxo-12-(6-oxo-octyl)-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-9-ylmethyl]-indol-1-yl}-acetic acid

ID: ALA1793977

PubChem CID: 10818029

Max Phase: Preclinical

Molecular Formula: C35H49N5O7

Molecular Weight: 651.81

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CCC(=O)CCCCC[C@@H]1NC(=O)[C@H]2CCCCN2C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](Cc2cn(CC(=O)O)c3ccccc23)NC1=O

Standard InChI:  InChI=1S/C35H49N5O7/c1-4-22(3)31-35(47)40-18-12-11-17-29(40)34(46)36-26(15-8-6-7-13-24(41)5-2)32(44)37-27(33(45)38-31)19-23-20-39(21-30(42)43)28-16-10-9-14-25(23)28/h9-10,14,16,20,22,26-27,29,31H,4-8,11-13,15,17-19,21H2,1-3H3,(H,36,46)(H,37,44)(H,38,45)(H,42,43)/t22-,26-,27-,29+,31-/m0/s1

Standard InChI Key:  SOGXSPMNYVWNRR-FTXZBAAWSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1793977

   cyclo[Aoda-Trp(EtO2H)(EtO2H)-Ile-D-Pip]

Molecule Features

Natural Product: No

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: 651.81

Molecular Weight (Monoisotopic): 651.3632

AlogP: 3.09

#Rotatable Bonds: 13

Polar Surface Area: 166.91

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.93

CX Basic pKa: ┄

CX LogP: 3.37

CX LogD: 0.17

Aromatic Rings: 2

Heavy Atoms: 47

QED Weighted: 0.24

Np Likeness Score: 0.71

References

1. Colletti SL, Myers RW, Darkin-Rattray SJ, Gurnett AM, Dulski PM, Galuska S, Allocco JJ, Ayer MB, Li C, Lim J, Crumley TM, Cannova C, Schmatz DM, Wyvratt MJ, Fisher MH, Meinke PT..  (2001)  Broad spectrum antiprotozoal agents that inhibit histone deacetylase: structure-activity relationships of apicidin. Part 2.,  11  (2): [PMID:11206439] [10.1016/s0960-894x(00)00605-3]

2. Meinke PT, Colletti SL, Doss G, Myers RW, Gurnett AM, Dulski PM, Darkin-Rattray SJ, Allocco JJ, Galuska S, Schmatz DM, Wyvratt MJ, Fisher MH..  (2000)  Synthesis of apicidin-derived quinolone derivatives: parasite-selective histone deacetylase inhibitors and antiproliferative agents.,  43  (25): [PMID:11124001] [10.1021/jm0001976]

Source

Source(1):

• Scientific Literature