(3S,6S,9S,12S,15S,18S)-18-((S)-1-((R)-1-((S)-2-((S)-2-amino-5-guanidinopentanamido)-3-phenylpropanoyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxamido)-3-carbamoyl-9-(4-hydroxybenzyl)-6,12-diisobutyl-2,15-dimethyl-5,8,11,14,17-pentaoxo-4,7,10,13,16-pentaazahenicosan-21-oic acid

ID: ALA4208342

PubChem CID: 145975747

Max Phase: Preclinical

Molecular Formula: C59H90N14O13

Molecular Weight: 1203.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1CCCN1C(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CCCNC(=N)N)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(N)=O)C(C)C

Standard InChI:  InChI=1S/C59H90N14O13/c1-32(2)28-41(53(81)69-43(30-37-19-21-38(74)22-20-37)54(82)68-42(29-33(3)4)55(83)71-48(34(5)6)49(61)77)67-50(78)35(7)65-52(80)40(23-24-47(75)76)66-56(84)45-17-12-26-72(45)58(86)46-18-13-27-73(46)57(85)44(31-36-14-9-8-10-15-36)70-51(79)39(60)16-11-25-64-59(62)63/h8-10,14-15,19-22,32-35,39-46,48,74H,11-13,16-18,23-31,60H2,1-7H3,(H2,61,77)(H,65,80)(H,66,84)(H,67,78)(H,68,82)(H,69,81)(H,70,79)(H,71,83)(H,75,76)(H4,62,63,64)/t35-,39-,40-,41-,42-,43-,44-,45-,46+,48-/m0/s1

Standard InChI Key:  UVRRPKMYSHUVOH-MZWLMSTQSA-N

Molfile:  

     RDKit          2D

 86 89  0  0  0  0  0  0  0  0999 V2000
   28.2588  -22.5113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2832  -23.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5917  -23.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0137  -23.7180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0311  -19.7013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7503  -20.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4245  -18.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4491  -19.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7751  -20.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4999  -21.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5244  -22.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1743  -20.0410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8730  -19.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2963  -19.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5923  -19.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8483  -18.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5086  -17.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5453  -18.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2608  -18.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9554  -18.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9287  -17.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2031  -17.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9659  -20.0178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0069  -20.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7832  -19.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4857  -20.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2032  -19.6566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1843  -18.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9241  -17.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9138  -18.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6315  -18.8714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3385  -18.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0501  -19.7115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3460  -17.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0576  -18.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7593  -18.4897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4784  -18.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1957  -17.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1843  -18.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4662  -19.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1853  -20.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1697  -20.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8917  -19.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9031  -18.8994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6062  -18.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3125  -19.7367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.3239  -18.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6165  -17.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3343  -16.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3276  -17.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0385  -17.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7522  -17.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7578  -16.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0469  -16.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4701  -16.0547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.0310  -18.5218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.7489  -18.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4620  -17.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4517  -18.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7378  -19.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4516  -20.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4402  -20.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1633  -19.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1736  -18.9234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.8725  -18.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5841  -19.7647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.5944  -18.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8875  -17.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5992  -17.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1737  -17.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3061  -18.5377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2981  -21.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6191  -20.8122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9965  -21.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2871  -22.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0912  -22.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4684  -20.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7454  -21.2070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8462  -21.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6315  -22.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0165  -21.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6270  -18.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8809  -17.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3237  -16.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5776  -16.0193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5126  -16.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8 12  1  0
 15 73  1  0
 24 78  1  0
 26 27  1  0
 30 31  1  0
 35 36  1  0
 39 44  1  0
 47 56  1  0
 59 64  1  0
 67 71  1  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  6  5  1  6
  6  8  1  0
  8  7  2  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11  1  1  0
 13 12  1  1
 13 15  1  0
 15 14  2  0
 13 16  1  0
 16 18  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 72 24  1  1
 24 23  2  0
 77 26  1  6
 26 25  2  0
 27 28  1  0
 28 30  1  0
 30 29  2  0
 31 32  1  0
 32 35  1  0
 35 33  2  0
 32 34  1  1
 37 36  1  6
 37 39  1  0
 39 38  2  0
 37 40  1  0
 40 41  1  0
 41 42  1  0
 41 43  1  0
 45 44  1  1
 45 47  1  0
 47 46  2  0
 45 48  1  0
 48 50  1  0
 49 50  2  0
 50 51  1  0
 51 52  2  0
 52 53  1  0
 53 54  2  0
 54 49  1  0
 53 55  1  0
 57 56  1  6
 57 59  1  0
 59 58  2  0
 57 60  1  0
 60 61  1  0
 61 62  1  0
 61 63  1  0
 65 64  1  1
 65 67  1  0
 67 66  2  0
 65 68  1  0
 68 69  1  0
 68 70  1  0
 72 73  1  0
 73 74  1  0
 74 75  1  0
 75 76  1  0
 76 72  1  0
 77 78  1  0
 78 79  1  0
 79 80  1  0
 80 81  1  0
 81 77  1  0
 28 82  1  1
 82 83  1  0
 83 84  1  0
 84 85  1  0
 84 86  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4208342

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1203.45

Molecular Weight (Monoisotopic): 1202.6812

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Yang D, Qin W, Shi X, Zhu B, Xie M, Zhao H, Teng B, Wu Y, Zhao R, Yin F, Ren P, Liu L, Li Z..  (2018)  Stabilized β-Hairpin Peptide Inhibits Insulin Degrading Enzyme.,  61  (18): [PMID:30148634] [10.1021/acs.jmedchem.8b00418]

Source

Source(1):

• Scientific Literature