(3S,6S,9S,12S,15S,18R,26R,29S)-18-[(2-aminoacetyl)amino]-9-(3-amino-3-oxo-propyl)-3-(carboxymethyl)-12-(3-guanidinopropyl)-15-[(1R)-1-hydroxyethyl]-6-(1H-indol-3-ylmethyl)-2,5,8,11,14,17,22,28-octaoxo-20,24-dithia-1,4,7,10,13,16,27-heptazabicyclo[27.3.0]dotriacontane-26-carboxylic acid

ID: ALA5185690

PubChem CID: 168279592

Max Phase: Preclinical

Molecular Formula: C46H66N14O15S2

Molecular Weight: 1119.25

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@@H]1NC(=O)[C@@H](NC(=O)CN)CSCC(=O)CSC[C@@H](C(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CC(=O)O)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(=N)N)NC1=O

Standard InChI:  InChI=1S/C46H66N14O15S2/c1-22(61)37-43(72)55-27(8-4-12-51-46(49)50)38(67)54-28(10-11-34(48)63)39(68)56-29(14-23-17-52-26-7-3-2-6-25(23)26)40(69)57-30(15-36(65)66)44(73)60-13-5-9-33(60)42(71)58-32(45(74)75)21-77-19-24(62)18-76-20-31(41(70)59-37)53-35(64)16-47/h2-3,6-7,17,22,27-33,37,52,61H,4-5,8-16,18-21,47H2,1H3,(H2,48,63)(H,53,64)(H,54,67)(H,55,72)(H,56,68)(H,57,69)(H,58,71)(H,59,70)(H,65,66)(H,74,75)(H4,49,50,51)/t22-,27+,28+,29+,30+,31+,32+,33+,37+/m1/s1

Standard InChI Key:  QRDGKQSDVDYEDD-WLLRZNNESA-N

Molfile:  

 
     RDKit          2D

 78 81  0  0  0  0  0  0  0  0999 V2000
   -2.5008   -5.2713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -4.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -4.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -3.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -3.6212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -2.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -2.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -1.5585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863    0.0915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863    0.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    1.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.9165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    2.1541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    2.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    2.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    2.5666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    2.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.9165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    0.9165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    0.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    1.3291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    0.0915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5968   -0.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3421   -1.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -1.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626   -0.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4657   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8822   -0.7630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958   -1.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124   -2.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -2.7961    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -3.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -4.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -4.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570   -3.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570   -2.7961    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8927   -1.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1063   -2.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053   -1.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2521    0.6172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    2.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    2.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    2.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    3.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    2.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679    3.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9780    3.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5258    4.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705    5.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    5.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9131    4.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    4.6607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335    3.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    1.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    4.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    5.0418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    5.0418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    1.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    2.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153    2.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153    3.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6443    3.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    4.6293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153    0.0915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153   -1.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153   -2.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298   -1.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -2.7961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1123    0.4180    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  3  4  2  0
  5  3  1  0
  6  5  1  6
  6  7  1  0
  7  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 27 26  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 35 34  1  0
 36 35  1  0
 37 36  1  0
 37 38  2  0
 39 37  1  0
 40 39  1  0
 40 41  1  0
  6 41  1  0
 33 42  1  6
 42 43  1  0
 42 44  2  0
 31 45  2  0
 23 46  1  1
 46 47  1  0
 47 48  1  0
 47 49  2  0
 19 50  1  1
 50 51  1  0
 52 51  1  0
 52 53  1  0
 53 54  2  0
 54 55  1  0
 55 56  2  0
 57 56  1  0
 57 52  2  0
 58 57  1  0
 59 58  1  0
 59 51  2  0
 17 60  2  0
 16 61  1  1
 61 62  1  0
 62 63  1  0
 63 64  1  0
 63 65  2  0
 12 66  1  1
 66 67  1  0
 67 68  1  0
 68 69  1  0
 69 70  1  0
 70 71  2  0
 70 72  1  0
 10 73  2  0
  9 74  1  0
 74 75  1  0
 74 76  1  1
  7 77  2  0
 30 78  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5185690

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1119.25

Molecular Weight (Monoisotopic): 1118.4273

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. Gonschorek P, Zorzi A, Maric T, Le Jeune M, Schüttel M, Montagnon M, Gómez-Ojea R, Vollmar DP, Whitfield C, Reymond L, Carle V, Verma H, Schilling O, Hovnanian A, Heinis C..  (2022)  Phage Display Selected Cyclic Peptide Inhibitors of Kallikrein-Related Peptidases 5 and 7 and Their In Vivo Delivery to the Skin.,  65  (14.0): [PMID:35653695] [10.1021/acs.jmedchem.2c00306]

Source

Source(1):

• Scientific Literature