(2S,5S,8S,11S,14S)-14-((S)-2-((S)-2-acetamido-3-hydroxypropanamido)-3-(1H-imidazol-5-yl)propanamido)-2-(3-guanidinopropyl)-8,11-diisobutyl-5-methyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazaheptadecane-1,17-dioic acid

ID: ALA1089590

PubChem CID: 46883588

Max Phase: Preclinical

Molecular Formula: C37H62N12O12

Molecular Weight: 866.97

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O

Standard InChI:  InChI=1S/C37H62N12O12/c1-18(2)12-25(32(56)43-20(5)30(54)46-24(36(60)61)8-7-11-41-37(38)39)48-33(57)26(13-19(3)4)47-31(55)23(9-10-29(52)53)45-34(58)27(14-22-15-40-17-42-22)49-35(59)28(16-50)44-21(6)51/h15,17-20,23-28,50H,7-14,16H2,1-6H3,(H,40,42)(H,43,56)(H,44,51)(H,45,58)(H,46,54)(H,47,55)(H,48,57)(H,49,59)(H,52,53)(H,60,61)(H4,38,39,41)/t20-,23-,24-,25-,26-,27-,28-/m0/s1

Standard InChI Key:  DXINZXKYNIRISG-AUUFLVQBSA-N

Molfile:  

     RDKit          2D

 61 61  0  0  0  0  0  0  0  0999 V2000
   -2.7839   -8.5906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711   -8.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543   -9.4221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543   -8.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711   -7.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3504   -6.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367   -8.1863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -8.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7884   -7.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7884   -8.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -9.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7491  -10.6717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186  -10.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310  -10.3151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737   -9.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900   -9.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135   -8.6035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221   -8.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9448   -9.4509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9448   -8.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221   -7.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451   -6.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451   -6.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684   -5.7265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376   -5.7389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6523   -8.2069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756   -8.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829   -7.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829   -8.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756   -9.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0828   -9.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0828  -10.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7901   -9.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8107   -8.6353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5133   -8.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2413   -9.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2413   -8.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5133   -7.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2413   -6.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2413   -6.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9647   -7.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9485   -8.2401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6719   -8.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3791   -7.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6719   -9.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3791   -8.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2563   -5.7932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2563   -4.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5534   -4.5649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9842   -4.5570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1024   -8.6686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8096   -8.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5330   -9.5130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5330   -8.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8096   -7.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5330   -7.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5330   -6.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2402   -8.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4951   -8.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921   -7.3514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122   -8.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20 26  1  0
 29 34  1  0
 37 42  1  0
 46 51  1  0
 54 58  1  0
  1  2  1  0
  2  4  1  0
  4  3  2  0
  2  5  1  1
  5  6  1  0
  7  8  1  0
  8 10  1  0
 10  9  2  0
  8 11  1  6
 11 16  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 12  1  0
 17 18  1  0
 18 20  1  0
 20 19  2  0
 18 21  1  1
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 26 27  1  0
 27 29  1  0
 29 28  2  0
 27 30  1  6
 30 31  1  0
 31 32  1  0
 31 33  1  0
 34 35  1  0
 35 37  1  0
 37 36  2  0
 35 38  1  1
 38 39  1  0
 39 40  1  0
 39 41  1  0
 42 43  1  0
 43 46  1  0
 46 44  2  0
 43 45  1  6
 47 48  1  0
 48 49  1  0
 48 50  2  0
 51 52  1  0
 52 54  1  0
 54 53  2  0
 52 55  1  1
 55 56  1  0
 56 57  1  0
 57 47  1  0
  1 59  1  0
  4  7  1  0
 10 17  1  0
 59 60  2  0
 59 61  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089590

   Ac-Ser-His-Glu-Leu-Leu-Ala-Arg-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: 866.97

Molecular Weight (Monoisotopic): 866.4610

AlogP: -3.32

#Rotatable Bonds: 28

Polar Surface Area: 389.11

Molecular Species: ZWITTERION

HBA: 12

HBD: 14

#RO5 Violations: 3

HBA (Lipinski): 24

HBD (Lipinski): 15

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.56

CX Basic pKa: 11.68

CX LogP: -8.06

CX LogD: -9.55

Aromatic Rings: 1

Heavy Atoms: 61

QED Weighted: 0.02

Np Likeness Score: 0.17

References

1. Ruiz-Gómez G, Lim J, Halili MA, Le GT, Madala PK, Abbenante G, Fairlie DP..  (2009)  Structure-activity relationships for substrate-based inhibitors of human complement factor B.,  52  (19): [PMID:19743866] [10.1021/jm900781m]

Source

Source(1):

• Scientific Literature