N-Ac-D-Ala-Arg{N-omega-(N-methylcarbanoyl)}-N-methyl-Phe-OH

ID: ALA522670

PubChem CID: 44572670

Max Phase: Preclinical

Molecular Formula: C23H35N7O6

Molecular Weight: 505.58

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CNC(=O)NC(=N)NCCC[C@H](NC(=O)[C@@H](C)NC(C)=O)C(=O)N(C)[C@@H](Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C23H35N7O6/c1-14(27-15(2)31)19(32)28-17(11-8-12-26-22(24)29-23(36)25-3)20(33)30(4)18(21(34)35)13-16-9-6-5-7-10-16/h5-7,9-10,14,17-18H,8,11-13H2,1-4H3,(H,27,31)(H,28,32)(H,34,35)(H4,24,25,26,29,36)/t14-,17+,18+/m1/s1

Standard InChI Key:  DDYKTARSFHNXGN-JLSDUUJJSA-N

Molfile:  

     RDKit          2D

 36 36  0  0  0  0  0  0  0  0999 V2000
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    4.4616  -18.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761  -18.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4616  -19.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7471  -19.9458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761  -19.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8905  -18.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6050  -18.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3195  -18.7083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0340  -18.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7484  -18.7083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0340  -17.4708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4629  -18.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1774  -18.7083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4629  -17.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1774  -19.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7471  -20.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4616  -21.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3182  -20.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327  -22.0083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4616  -22.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453  -22.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7449  -23.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4599  -23.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1768  -23.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1736  -22.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327  -19.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7471  -17.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327  -17.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4616  -17.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327  -16.2333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3182  -17.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7471  -15.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7471  -14.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4616  -16.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 17 19  1  1
  9 10  1  0
 18 20  2  0
  2  3  1  1
 18 21  1  0
 10 11  1  0
 19 22  1  0
  4  6  2  0
 22 23  2  0
 10 12  2  0
 23 24  1  0
  1  2  1  0
 24 25  2  0
 11 13  1  0
 25 26  1  0
  3  7  1  0
 26 27  2  0
 27 22  1  0
 13 14  1  0
  5 28  1  0
  2  4  1  0
  1 29  1  0
 13 15  2  0
 29 30  1  0
  7  8  1  0
 29 31  2  0
 14 16  1  0
 30 32  1  0
 30 33  1  1
  5 17  1  0
 32 34  1  0
  8  9  1  0
 34 35  1  0
 17 18  1  0
 34 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA522670

   N-Ac-D-Ala-Arg{N-omega-(N-methylcarbanoyl)}-N-methyl-Phe-OH

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: 505.58

Molecular Weight (Monoisotopic): 505.2649

AlogP: -0.62

#Rotatable Bonds: 12

Polar Surface Area: 192.82

Molecular Species: ZWITTERION

HBA: 6

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.01

CX Basic pKa: 9.43

CX LogP: -2.69

CX LogD: -2.69

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.11

Np Likeness Score: -0.12

References

1. Sunazuka T, Sugawara A, Iguchi K, Hirose T, Nagai K, Noguchi Y, Saito Y, Yamamoto T, Ui H, Gouda H, Shiomi K, Watanabe T, Omura S..  (2009)  Argifin; efficient solid phase total synthesis and evaluation of analogues of acyclic peptide.,  17  (7): [PMID:19297173] [10.1016/j.bmc.2009.02.047]

Source

Source(1):

• Scientific Literature