2-((6S,9S,12S,15S,18S,21S,23aS,28aR)-18-benzyl-6-butyl-21-(3-guanidinopropyl)-9-methyl-5,8,11,14,17,20,23,28-octaoxo-15-phenethyloctacosahydrodipyrrolo[1,2-a:1',2'-d][1,4,7,10,13,16,19,22]octaazacyclotetracosin-12-yl)acetamide

ID: ALA4174361

PubChem CID: 145951904

Max Phase: Preclinical

Molecular Formula: C48H68N12O9

Molecular Weight: 957.15

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCC[C@@H]1NC(=O)[C@H](C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCc2ccccc2)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]2CCCN2C(=O)[C@H]2CCCN2C1=O

Standard InChI:  InChI=1S/C48H68N12O9/c1-3-4-18-34-46(68)60-26-13-21-38(60)47(69)59-25-12-20-37(59)45(67)55-32(19-11-24-52-48(50)51)41(63)57-35(27-31-16-9-6-10-17-31)44(66)54-33(23-22-30-14-7-5-8-15-30)42(64)58-36(28-39(49)61)43(65)53-29(2)40(62)56-34/h5-10,14-17,29,32-38H,3-4,11-13,18-28H2,1-2H3,(H2,49,61)(H,53,65)(H,54,66)(H,55,67)(H,56,62)(H,57,63)(H,58,64)(H4,50,51,52)/t29-,32-,33-,34-,35-,36-,37-,38+/m0/s1

Standard InChI Key:  JOKDUJYLRRCMRY-PZMAVKSXSA-N

Molfile:  

     RDKit          2D

 69 73  0  0  0  0  0  0  0  0999 V2000
   16.6573  -18.5823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4060  -18.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1223  -18.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1224  -19.4831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8343  -19.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5461  -19.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2666  -19.8996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9784  -19.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9783  -18.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6902  -18.2495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6901  -17.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9781  -17.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9780  -16.1872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2661  -15.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5456  -16.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8337  -15.7794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1219  -16.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4057  -15.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6938  -16.1878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9819  -15.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2614  -16.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5495  -15.7800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7966  -16.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6271  -16.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8408  -17.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2493  -15.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6572  -14.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4639  -14.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2616  -17.0128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4056  -14.9545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1220  -17.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5457  -17.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2660  -14.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9778  -14.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9777  -13.7166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6898  -14.9540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2663  -17.4291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4062  -17.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1181  -17.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2664  -18.2497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6904  -19.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6905  -20.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4024  -21.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4025  -21.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6907  -22.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9787  -21.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9786  -21.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5460  -18.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8344  -20.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5463  -21.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5464  -21.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8346  -22.3704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1227  -21.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4066  -22.3705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1226  -21.1330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8341  -18.2499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3204  -17.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5137  -17.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1012  -17.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8618  -17.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6048  -17.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3480  -17.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3513  -16.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6053  -15.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8608  -16.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9830  -14.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2369  -14.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2379  -13.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4962  -13.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  1  0
  5  4  1  6
  5  6  1  0
  6  7  1  0
  8  7  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 24  1  1  0
 24 25  2  0
 23 26  1  0
 27 26  1  0
 28 27  1  0
 28 22  1  0
 21 29  2  0
 18 30  2  0
 17 31  1  1
 15 32  2  0
 14 33  1  6
 33 34  1  0
 34 35  2  0
 34 36  1  0
 12 37  2  0
 11 38  1  6
 38 39  1  0
  9 40  2  0
  8 41  1  6
 41 42  1  0
 43 42  2  0
 44 43  1  0
 45 44  2  0
 46 45  1  0
 47 46  2  0
 42 47  1  0
  6 48  2  0
  5 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  0
 53 55  2  0
  3 56  2  0
  2 57  1  0
 58 57  1  0
 59 58  1  0
 59  1  1  0
 39 60  1  0
 60 61  2  0
 61 62  1  0
 62 63  2  0
 63 64  1  0
 64 65  2  0
 65 60  1  0
 20 66  1  6
 66 67  1  0
 67 68  1  0
 68 69  1  0
M  END

Alternative Forms

  1. Parent:

    ALA4174361

    ---

Associated Targets(non-human)

Mc5r Melanocortin receptor 5 (870 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mc1r Melanocortin receptor 1 (1101 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mc4r Melanocortin receptor 4 (1205 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mc3r Melanocortin receptor 3 (1119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Biocomponents

Calculated Properties

Molecular Weight: 957.15Molecular Weight (Monoisotopic): 956.5232AlogP: -0.88#Rotatable Bonds: 14
Polar Surface Area: 320.21Molecular Species: BASEHBA: 10HBD: 10
#RO5 Violations: 2HBA (Lipinski): 21HBD (Lipinski): 12#RO5 Violations (Lipinski): 3
CX Acidic pKa: 11.52CX Basic pKa: 11.37CX LogP: -1.63CX LogD: -3.34
Aromatic Rings: 2Heavy Atoms: 69QED Weighted: 0.06Np Likeness Score: 0.54

References

1. Fleming KA, Freeman KT, Ericson MD, Haskell-Luevano C..  (2018)  Synergistic Multiresidue Substitutions of a Macrocyclic c[Pro-Arg-Phe-Phe-Asn-Ala-Phe-dPro] Agouti-Related Protein (AGRP) Scaffold Yield Potent and >600-Fold MC4R versus MC3R Selective Melanocortin Receptor Antagonists.,  61  (17): [PMID:30035543] [10.1021/acs.jmedchem.8b00684]

Source