1-(3-((6S,9S,12S,15S,18S,21S,23aS,28aR)-12-(aminomethyl)-6,18-dibenzyl-9-(hydroxymethyl)-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-21-yl)propyl)guanidine

ID: ALA4174761

PubChem CID: 145951686

Max Phase: Preclinical

Molecular Formula: C50H66N12O9

Molecular Weight: 979.15

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: N=C(N)NCCC[C@@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@H]2CCCN2C(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CO)NC(=O)[C@H](CN)NC(=O)[C@H](CCc2ccccc2)NC(=O)[C@H](Cc2ccccc2)NC1=O

Standard InChI: InChI=1S/C50H66N12O9/c51-29-38-45(67)60-39(30-63)46(68)58-37(28-33-17-8-3-9-18-33)48(70)62-26-12-21-41(62)49(71)61-25-11-20-40(61)47(69)56-34(19-10-24-54-50(52)53)42(64)57-36(27-32-15-6-2-7-16-32)44(66)55-35(43(65)59-38)23-22-31-13-4-1-5-14-31/h1-9,13-18,34-41,63H,10-12,19-30,51H2,(H,55,66)(H,56,69)(H,57,64)(H,58,68)(H,59,65)(H,60,67)(H4,52,53,54)/t34-,35-,36-,37-,38-,39-,40-,41+/m0/s1

Standard InChI Key: YKHASWSLDVHIPY-JTPPURIGSA-N

Molfile:

     RDKit          2D

 71 76  0  0  0  0  0  0  0  0999 V2000
   31.0435  -28.6319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7924  -28.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5086  -28.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5087  -29.5326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2206  -29.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9323  -29.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6530  -29.9492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3648  -29.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3647  -28.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0766  -28.2946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0765  -27.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3645  -27.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3644  -26.2367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6524  -25.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9319  -26.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2201  -25.8246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5083  -26.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7921  -25.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0801  -26.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3682  -25.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6478  -26.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9359  -25.8251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1828  -26.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0134  -26.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2270  -27.2237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6355  -25.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0436  -24.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8502  -25.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6479  -27.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7919  -24.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5084  -27.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9320  -27.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6523  -24.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3641  -24.5911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6527  -27.4743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7926  -27.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5045  -27.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6528  -28.2949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0768  -29.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0769  -30.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7887  -31.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7888  -32.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0771  -32.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3651  -32.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3650  -31.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9322  -28.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2207  -30.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9325  -31.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9326  -32.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2209  -32.4199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5090  -32.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7929  -32.4200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5089  -31.1825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2204  -28.2951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7067  -27.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9000  -27.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4876  -28.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2482  -27.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9912  -27.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7343  -27.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7376  -26.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9915  -25.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2471  -26.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3693  -24.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9307  -24.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3633  -23.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9255  -22.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0608  -22.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6358  -23.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0719  -24.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2507  -27.4886    0.0000 O   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
 12 35  2  0
 11 36  1  6
 36 37  1  0
  9 38  2  0
  8 39  1  6
 39 40  1  0
 41 40  2  0
 42 41  1  0
 43 42  2  0
 44 43  1  0
 45 44  2  0
 40 45  1  0
  6 46  2  0
  5 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  1  0
 51 53  2  0
  3 54  2  0
  2 55  1  0
 56 55  1  0
 57 56  1  0
 57  1  1  0
 37 58  1  0
 58 59  2  0
 59 60  1  0
 60 61  2  0
 61 62  1  0
 62 63  2  0
 63 58  1  0
 20 64  1  6
 64 65  1  0
 65 66  2  0
 66 67  1  0
 67 68  2  0
 68 69  1  0
 69 70  2  0
 70 65  1  0
 31 71  1  0
M  END

Associated Targets(non-human)

Mc5r Melanocortin receptor 5 (870 Activities)

Discover Target: Mc5r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc1r Melanocortin receptor 1 (1101 Activities)

Discover Target: Mc1r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc4r Melanocortin receptor 4 (1205 Activities)

Discover Target: Mc4r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc3r Melanocortin receptor 3 (1119 Activities)

Discover Target: Mc3r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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: 979.15	Molecular Weight (Monoisotopic): 978.5076	AlogP: -1.78	#Rotatable Bonds: 13
Polar Surface Area: 323.37	Molecular Species: BASE	HBA: 11	HBD: 11
#RO5 Violations: 3	HBA (Lipinski): 21	HBD (Lipinski): 13	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 11.43	CX Basic pKa: 11.41	CX LogP: -2.12	CX LogD: -4.62
Aromatic Rings: 3	Heavy Atoms: 71	QED Weighted: 0.05	Np Likeness Score: 0.50

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]

1-(3-((6S,9S,12S,15S,18S,21S,23aS,28aR)-12-(aminomethyl)-6,18-dibenzyl-9-(hydroxymethyl)-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-21-yl)propyl)guanidine

Names and Identifiers

Alternative Forms

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source