(3S,6S,9S,12S,15R,23R,26S)-15-[(2-aminoacetyl)amino]-6-(3-amino-3-oxo-propyl)-9-(3-guanidinopropyl)-12-[(1R)-1-hydroxyethyl]-3-[(4-hydroxyphenyl)methyl]-2,5,8,11,14,19,25-heptaoxo-17,21-dithia-1,4,7,10,13,24-hexazabicyclo[24.3.0]nonacosane-23-carboxylic acid

ID: ALA5205331

PubChem CID: 168295844

Max Phase: Preclinical

Molecular Formula: C40H60N12O13S2

Molecular Weight: 981.12

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](Cc2ccc(O)cc2)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(=N)N)NC1=O

Standard InChI:  InChI=1S/C40H60N12O13S2/c1-20(53)32-37(62)48-24(4-2-12-45-40(43)44)33(58)47-25(10-11-30(42)56)34(59)49-26(14-21-6-8-22(54)9-7-21)38(63)52-13-3-5-29(52)36(61)50-28(39(64)65)19-67-17-23(55)16-66-18-27(35(60)51-32)46-31(57)15-41/h6-9,20,24-29,32,53-54H,2-5,10-19,41H2,1H3,(H2,42,56)(H,46,57)(H,47,58)(H,48,62)(H,49,59)(H,50,61)(H,51,60)(H,64,65)(H4,43,44,45)/t20-,24+,25+,26+,27+,28+,29+,32+/m1/s1

Standard InChI Key:  PBSQXKHCZCXSLI-VOYJGBGOSA-N

Molfile:  

 
     RDKit          2D

 68 70  0  0  0  0  0  0  0  0999 V2000
   -2.1433   -3.9176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288   -4.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288   -5.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -5.5676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -3.9176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -3.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288   -2.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288   -1.8551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -0.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288   -0.2051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288    0.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.8572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.2697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    1.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.6197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -0.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938   -0.2194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -1.4640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -1.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2867   -1.8551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -0.6177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -2.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -3.0926    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -3.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.1551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -3.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -3.0926    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506   -0.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1628    0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6111    0.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    3.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442    3.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442    4.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8589    4.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5754    4.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5754    3.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8589    5.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    3.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    4.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.7447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    1.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577    2.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577    3.0947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    3.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2867    3.0947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    4.3322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577   -0.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577   -1.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577   -2.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722   -1.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -3.0926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0779   -1.0141    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  5  2  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
 23 22  1  0
 23 24  1  0
 24 25  2  0
 26 24  1  0
 27 26  1  0
 27 28  1  6
 28 29  1  0
 28 30  2  0
 27 31  1  0
 32 31  1  0
 33 32  1  0
 34 33  1  0
 34 35  2  0
 36 34  1  0
 37 36  1  0
 37 38  1  0
  6 38  1  0
 39 23  1  0
 40 39  1  0
 41 40  1  0
 41 22  1  0
 19 42  1  1
 42 43  1  0
 44 43  2  0
 45 44  1  0
 46 45  2  0
 47 46  1  0
 48 47  2  0
 43 48  1  0
 46 49  1  0
 17 50  2  0
 16 51  1  1
 51 52  1  0
 52 53  1  0
 53 54  1  0
 53 55  2  0
 12 56  1  1
 56 57  1  0
 57 58  1  0
 58 59  1  0
 59 60  1  0
 60 61  2  0
 60 62  1  0
 10 63  2  0
  9 64  1  0
 64 65  1  0
 64 66  1  1
  7 67  2  0
 23 68  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5205331

   ---

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: 981.12

Molecular Weight (Monoisotopic): 980.3844

AlogP: -5.16

#Rotatable Bonds: 13

Polar Surface Area: 420.75

Molecular Species: ZWITTERION

HBA: 16

HBD: 14

#RO5 Violations: 3

HBA (Lipinski): 25

HBD (Lipinski): 17

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.68

CX Basic pKa: 12.40

CX LogP: -8.00

CX LogD: -8.31

Aromatic Rings: 1

Heavy Atoms: 67

QED Weighted: 0.05

Np Likeness Score: 0.70

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