(6S,9S,12S,14aR)-9-(2-Bromo-1H-indol-3-ylmethyl)-6-sec-butyl-12-(6-oxo-octyl)-decahydro-4a,7,10,13-tetraaza-benzocyclododecene-5,8,11,14-tetraone

ID: ALA1793975

PubChem CID: 15484556

Max Phase: Preclinical

Molecular Formula: C33H46BrN5O5

Molecular Weight: 672.66

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](Cc2c(Br)[nH]c3ccccc23)NC1=O

Standard InChI:  InChI=1S/C33H46BrN5O5/c1-4-20(3)28-33(44)39-18-12-11-17-27(39)32(43)36-25(16-8-6-7-13-21(40)5-2)30(41)37-26(31(42)38-28)19-23-22-14-9-10-15-24(22)35-29(23)34/h9-10,14-15,20,25-28,35H,4-8,11-13,16-19H2,1-3H3,(H,36,43)(H,37,41)(H,38,42)/t20-,25-,26-,27+,28-/m0/s1

Standard InChI Key:  WSPZAXPNRNZYQV-SOJMTTIHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1793975

   cyclo[Aoda-Trp(2-Br)-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: 672.66

Molecular Weight (Monoisotopic): 671.2682

AlogP: 4.30

#Rotatable Bonds: 11

Polar Surface Area: 140.47

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.74

CX Basic pKa: ┄

CX LogP: 4.14

CX LogD: 4.14

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.26

Np Likeness Score: 1.24

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]

Source

Source(1):

• Scientific Literature