ID: ALA4065973

Max Phase: Preclinical

Molecular Formula: C97H159BrN34O20

Molecular Weight: 2201.46

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CCCCN)C(=O)NC(C)(C)C(=O)N[C@@H](Cc1ccc(Br)cc1)C(=O)O

Standard InChI:  InChI=1S/C97H159BrN34O20/c1-7-8-25-64(85(144)129-97(4,5)92(152)128-70(91(150)151)49-57-33-35-58(98)36-34-57)122-86(145)72-31-20-45-131(72)76(135)52-116-78(137)61(26-13-15-40-100)118-83(142)69(50-59-51-111-54-117-59)126-84(143)71(53-133)127-88(147)74(47-55(2)3)130(6)89(148)66(29-18-43-114-95(107)108)124-87(146)73-32-21-46-132(73)90(149)67(30-19-44-115-96(109)110)123-81(140)65(37-38-75(102)134)121-80(139)62(27-16-41-112-93(103)104)119-79(138)63(28-17-42-113-94(105)106)120-82(141)68(48-56-22-10-9-11-23-56)125-77(136)60(101)24-12-14-39-99/h9-11,22-23,33-36,51,54-55,60-74,133H,7-8,12-21,24-32,37-50,52-53,99-101H2,1-6H3,(H2,102,134)(H,111,117)(H,116,137)(H,118,142)(H,119,138)(H,120,141)(H,121,139)(H,122,145)(H,123,140)(H,124,146)(H,125,136)(H,126,143)(H,127,147)(H,128,152)(H,129,144)(H,150,151)(H4,103,104,112)(H4,105,106,113)(H4,107,108,114)(H4,109,110,115)/t60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-/m0/s1

Standard InChI Key:  KLQZDNWCYDAAMM-MOBVNWGTSA-N

Molecule Features

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

Properties

Molecular Weight: 2201.46

Molecular Weight (Monoisotopic): 2199.1653

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. McKinnie SMK, Wang W, Fischer C, McDonald T, Kalin KR, Iturrioz X, Llorens-Cortes C, Oudit GY, Vederas JC..  (2017)  Synthetic Modification within the "RPRL" Region of Apelin Peptides: Impact on Cardiovascular Activity and Stability to Neprilysin and Plasma Degradation.,  60  (14): [PMID:28685579] [10.1021/acs.jmedchem.7b00723]

2. Fischer C, Lamer T, Wang W, McKinnie SMK, Iturrioz X, Llorens-Cortes C, Oudit GY, Vederas JC..  (2019)  Plasma kallikrein cleaves and inactivates apelin-17: Palmitoyl- and PEG-extended apelin-17 analogs as metabolically stable blood pressure-lowering agents.,  166  [PMID:30690406] [10.1016/j.ejmech.2019.01.040]

3. Fischer C,Lamer T,Fernandez K,Gheblawi M,Wang W,Pascoe C,Lambkin G,Iturrioz X,Llorens-Cortes C,Oudit GY,Vederas JC.  (2020)  Optimizing PEG-Extended Apelin Analogues as Cardioprotective Drug Leads: Importance of the KFRR Motif and Aromatic Head Group for Improved Physiological Activity.,  63  (20): [PMID:33001648] [10.1021/acs.jmedchem.0c01395]

4. Fernandez KX, Fischer C, Vu J, Gheblawi M, Wang W, Gottschalk S, Iturrioz X, Llorens-Cortés C, Oudit GY, Vederas JC..  (2021)  Metabolically stable apelin-analogues, incorporating cyclohexylalanine and homoarginine, as potent apelin receptor activators.,  12  (8.0): [PMID:34458742] [10.1039/D1MD00120E]

Source

Source(1):

• Scientific Literature