1,-(3,3'-((6S,9S,12S,15S,18S,21S,23aS,28aR)-18-benzyl-6-butyl-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]octaazacyclotetracosine-12,21-diyl)bis(propane-3,1-diyl))diguanidine

ID: ALA4163787

PubChem CID: 145957551

Max Phase: Preclinical

Molecular Formula: C50H74N14O9

Molecular Weight: 1015.23

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CCCC[C@@H]1NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)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/C50H74N14O9/c1-2-3-18-36-47(72)64-28-13-22-40(64)48(73)63-27-12-21-39(63)46(71)59-34(20-11-26-56-50(53)54)41(66)61-37(29-32-16-8-5-9-17-32)44(69)58-35(24-23-31-14-6-4-7-15-31)43(68)57-33(19-10-25-55-49(51)52)42(67)62-38(30-65)45(70)60-36/h4-9,14-17,33-40,65H,2-3,10-13,18-30H2,1H3,(H,57,68)(H,58,69)(H,59,71)(H,60,70)(H,61,66)(H,62,67)(H4,51,52,55)(H4,53,54,56)/t33-,34-,35-,36-,37-,38-,39-,40+/m0/s1

Standard InChI Key: AQTAIKFZTTZGCE-ZHECQJHESA-N

Molfile:

     RDKit          2D

 73 77  0  0  0  0  0  0  0  0999 V2000
    6.3075  -19.4576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0562  -19.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7724  -19.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7725  -20.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4844  -20.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1962  -20.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9168  -20.7705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6286  -20.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6285  -19.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3404  -19.1204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3403  -18.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6283  -17.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6282  -17.0580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9162  -16.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1958  -17.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4839  -16.6502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7721  -17.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0559  -16.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3440  -17.0586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6320  -16.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9116  -17.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1997  -16.6508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4466  -16.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2772  -17.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4909  -18.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8994  -16.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3074  -15.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1140  -15.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9117  -17.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0558  -15.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7722  -17.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1959  -17.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9161  -15.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9165  -18.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0564  -17.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7683  -18.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9166  -19.1206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3406  -20.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3407  -21.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0526  -22.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0527  -22.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3409  -23.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6289  -22.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6288  -22.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1961  -19.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4845  -21.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1964  -22.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1965  -22.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4847  -23.2412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7728  -22.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0567  -23.2413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7727  -22.0082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4842  -19.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9705  -18.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1639  -18.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7514  -18.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5120  -17.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2550  -18.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9981  -17.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0015  -17.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2554  -16.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5109  -17.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6331  -15.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870  -15.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8881  -14.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1463  -14.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6583  -15.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6582  -14.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4005  -14.1093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4004  -13.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1426  -12.8204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6580  -12.8206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5145  -18.3144    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
 12 34  2  0
 11 35  1  6
 35 36  1  0
  9 37  2  0
  8 38  1  6
 38 39  1  0
 40 39  2  0
 41 40  1  0
 42 41  2  0
 43 42  1  0
 44 43  2  0
 39 44  1  0
  6 45  2  0
  5 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  1  0
 50 52  2  0
  3 53  2  0
  2 54  1  0
 55 54  1  0
 56 55  1  0
 56  1  1  0
 36 57  1  0
 57 58  2  0
 58 59  1  0
 59 60  2  0
 60 61  1  0
 61 62  2  0
 62 57  1  0
 20 63  1  6
 63 64  1  0
 64 65  1  0
 65 66  1  0
 33 67  1  0
 67 68  1  0
 68 69  1  0
 69 70  1  0
 70 71  1  0
 70 72  2  0
 31 73  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: 1015.23	Molecular Weight (Monoisotopic): 1014.5763	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. 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,-(3,3'-((6S,9S,12S,15S,18S,21S,23aS,28aR)-18-benzyl-6-butyl-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]octaazacyclotetracosine-12,21-diyl)bis(propane-3,1-diyl))diguanidine

Names and Identifiers

Alternative Forms

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source