(S)-2-{(R)-2-[(3,5-Dimethyl-benzoyl)-methyl-amino]-3-phenyl-propionylamino}-3-(1H-indol-3-yl)-propionic acid

ID: ALA439759

Chembl Id: CHEMBL439759

Cas Number: 169544-71-2

PubChem CID: 9848710

Max Phase: Preclinical

Molecular Formula: C30H31N3O4

Molecular Weight: 497.60

Molecule Type: Small molecule

Names and Identifiers

Synonyms: IRL-1841 | IRL-1841|169544-71-2|CHEMBL439759|(2S)-2-[[(2R)-2-[(3,5-dimethylbenzoyl)-methylamino]-3-phenylpropanoyl]amino]-3-(1H-indol-3-yl)propanoic acid|SCHEMBL8721943|DTXSID80431752|BDBM50071431|(S)-2-{(R)-2-[(3,5-Dimethyl-benzoyl)-methyl-amino]-3-phenyl-propionylamino}-3-(1H-indol-3-yl)-propionic acid|(S)-3-(1H-Indol-3-yl)-2-((R)-3-phenyl-2-(N,3,5-trimethylbenzamido)propanamido)propanoic acid

Canonical SMILES:  Cc1cc(C)cc(C(=O)N(C)[C@H](Cc2ccccc2)C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)O)c1

Standard InChI:  InChI=1S/C30H31N3O4/c1-19-13-20(2)15-22(14-19)29(35)33(3)27(16-21-9-5-4-6-10-21)28(34)32-26(30(36)37)17-23-18-31-25-12-8-7-11-24(23)25/h4-15,18,26-27,31H,16-17H2,1-3H3,(H,32,34)(H,36,37)/t26-,27+/m0/s1

Standard InChI Key:  JFNANCYIHVAEQV-RRPNLBNLSA-N

Alternative Forms

1. Parent:

   

   ALA439759

   (2S)-2-[[(2R)-2-[(3,5-dimethylbenzoyl)-methylamino]-3-phenylpropanoyl]amino]-3-(1H-indol-3-yl)propanoic acid

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

Calculated Properties

Molecular Weight: 497.60

Molecular Weight (Monoisotopic): 497.2315

AlogP: 4.28

#Rotatable Bonds: 9

Polar Surface Area: 102.50

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.91

CX Basic pKa: ┄

CX LogP: 5.22

CX LogD: 2.01

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.32

Np Likeness Score: -0.24

References

1. Sakaki J, Murata T, Yuumoto Y, Nakamura I, Trueh T, Pitterna T, Iwasaki G, Oda K, Yamamura T, Hayakawa K..  (1998)  Discovery of IRL 3461: a novel and potent endothelin antagonist with balanced ETA/ETB affinity.,  8  (16): [PMID:9873521] [10.1016/s0960-894x(98)00387-4]

2. Fruh T, Saika H, Svensson L, Pitterna T, Sakaki J, Okada T, Urade Y, Oda K, Fujitani Y, Takimoto M, Yamamura T, Inui T, Makatani M, Umemura I, Teno N, Toh H, Hayakawa K, Murata T.  (1996)  IRL 2500: A potent ETB selective endothelin antagonist,  6  (19): [10.1016/0960-894X(96)00421-0]

3. Goldstein SR, Liu C, Safo MK, Nakagawa A, Zapol WM, Winkler JD..  (2018)  Design, Synthesis, and Biological Evaluation of Allosteric Effectors That Enhance CO Release from Carboxyhemoglobin.,  9  (7): [PMID:30034606] [10.1021/acsmedchemlett.8b00166]

Source

Source(1):

• Scientific Literature