[(2R,5S,8R,14R,17S)-8,14-Bis-(4-amino-butyl)-17-(4-hydroxy-benzyl)-5-((R)-1-hydroxy-ethyl)-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16hexaaza-cyclooctadec-2-yl]-acetic acid

ID: ALA364059

PubChem CID: 44403761

Max Phase: Preclinical

Molecular Formula: C31H48N8O10

Molecular Weight: 692.77

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@@H]1NC(=O)[C@@H](CC(=O)O)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](CCCCN)NC(=O)CNC(=O)[C@@H](CCCCN)NC1=O

Standard InChI:  InChI=1S/C31H48N8O10/c1-17(40)26-31(49)36-20(6-2-4-12-32)27(45)34-16-24(42)35-21(7-3-5-13-33)28(46)37-22(14-18-8-10-19(41)11-9-18)29(47)38-23(15-25(43)44)30(48)39-26/h8-11,17,20-23,26,40-41H,2-7,12-16,32-33H2,1H3,(H,34,45)(H,35,42)(H,36,49)(H,37,46)(H,38,47)(H,39,48)(H,43,44)/t17-,20-,21-,22+,23-,26+/m1/s1

Standard InChI Key:  XSMRSYLZUDEPJP-LXGSKCJPSA-N

Molfile:  

     RDKit          2D

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    2.9750   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1167   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730    2.4859    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  5  1  1  0
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  8  4  1  0
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 12 24  1  1
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  2 26  1  0
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 18 41  1  6
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 48 46  1  0
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 37 31  2  0
  2 50  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA364059

   cyclo[D-Asp-Thr-D-Lys-Gly-D-Lys-Tyr]

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: 692.77

Molecular Weight (Monoisotopic): 692.3493

AlogP: -3.40

#Rotatable Bonds: 13

Polar Surface Area: 304.40

Molecular Species: ZWITTERION

HBA: 11

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.92

CX Basic pKa: 10.25

CX LogP: -7.33

CX LogD: -8.63

Aromatic Rings: 1

Heavy Atoms: 49

QED Weighted: 0.09

Np Likeness Score: 1.15

References

1. Liu J, Ying J, Chow VT, Hruby VJ, Satyanarayanajois SD..  (2005)  Structure-activity studies of peptides from the "hot-spot" region of human CD2 protein: development of peptides for immunomodulation.,  48  (20): [PMID:16190751] [10.1021/jm0503547]

Source

Source(1):

• Scientific Literature