3-[(2R,5S,8R,11S,14R,17S)-5,17-Bis-(4-amino-butyl)-11-benzyl-8-(2-carboxy-ethyl)-14-(3-guanidino-propyl)-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16hexaaza-cyclooctadec-2-yl]-propionic acid

ID: ALA364707

PubChem CID: 44403757

Max Phase: Preclinical

Molecular Formula: C37H59N11O10

Molecular Weight: 817.95

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NCCCC[C@@H]1NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](CCC(=O)O)NC1=O

Standard InChI:  InChI=1S/C37H59N11O10/c38-18-6-4-11-23-31(53)46-26(14-16-29(49)50)34(56)44-24(12-5-7-19-39)32(54)47-27(15-17-30(51)52)35(57)48-28(21-22-9-2-1-3-10-22)36(58)45-25(33(55)43-23)13-8-20-42-37(40)41/h1-3,9-10,23-28H,4-8,11-21,38-39H2,(H,43,55)(H,44,56)(H,45,58)(H,46,53)(H,47,54)(H,48,57)(H,49,50)(H,51,52)(H4,40,41,42)/t23-,24-,25+,26+,27+,28-/m0/s1

Standard InChI Key:  UECOOOOFJTVXST-UBUZFBQHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA364707

   cyclo[D-Arg-Lys-D-Glu-Lys-D-Glu-Phe]

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: 817.95

Molecular Weight (Monoisotopic): 817.4446

AlogP: -2.81

#Rotatable Bonds: 20

Polar Surface Area: 365.64

Molecular Species: ZWITTERION

HBA: 11

HBD: 12

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 16

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.68

CX Basic pKa: 10.55

CX LogP: -7.88

CX LogD: -9.79

Aromatic Rings: 1

Heavy Atoms: 58

QED Weighted: 0.04

Np Likeness Score: 0.57

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