(S)-2-((R)-2-{[(3S,6S,12R)-12-(3-Guanidino-propyl)-5,11,14-trioxo-20-oxa-4,10,13-triaza-tricyclo[19.2.2.0*6,10*]pentacosa-1(24),21(25),22-triene-3-carbonyl]-amino}-3-methyl-pentanoylamino)-4-methyl-pentanoic acid

ID: ALA1790704

PubChem CID: 56665343

Max Phase: Preclinical

Molecular Formula: C38H60N8O8

Molecular Weight: 756.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](C)[C@@H](NC(=O)[C@@H]1Cc2ccc(cc2)OCCCCCC(=O)N[C@H](CCCN=C(N)N)C(=O)N2CCC[C@H]2C(=O)N1)C(=O)N[C@@H](CC(C)C)C(=O)O

Standard InChI:  InChI=1S/C38H60N8O8/c1-5-24(4)32(35(50)44-29(37(52)53)21-23(2)3)45-33(48)28-22-25-14-16-26(17-15-25)54-20-8-6-7-13-31(47)42-27(11-9-18-41-38(39)40)36(51)46-19-10-12-30(46)34(49)43-28/h14-17,23-24,27-30,32H,5-13,18-22H2,1-4H3,(H,42,47)(H,43,49)(H,44,50)(H,45,48)(H,52,53)(H4,39,40,41)/t24-,27-,28+,29+,30+,32-/m1/s1

Standard InChI Key:  LTVAGLBMDPWQGE-PGHZORDASA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1790704

   (2S)-2-[[(2R,3R)-2-[[(3S,6S,12R)-12-[3-(diaminomethylideneamino)propyl]-5,11,14-trioxo-20-oxa-4,10,13-triazatricyclo[19.2.2.06,10]pentacosa-1(24),21(25),22-triene-3-carbonyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoic 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: 756.95

Molecular Weight (Monoisotopic): 756.4534

AlogP: 1.34

#Rotatable Bonds: 13

Polar Surface Area: 247.64

Molecular Species: ZWITTERION

HBA: 8

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.11

CX Basic pKa: 10.83

CX LogP: -0.04

CX LogD: -0.04

Aromatic Rings: 1

Heavy Atoms: 54

QED Weighted: 0.09

Np Likeness Score: 0.78

References

1. Lundquist JT, Dix TA..  (1999)  Preparation and receptor binding affinities of cyclic C-terminal neurotensin (8-13) and (9-13) analogues.,  9  (17): [PMID:10498212] [10.1016/s0960-894x(99)00420-5]

2. Chalon, P P and 8 more authors.  1996-05-20  Molecular cloning of a levocabastine-sensitive neurotensin binding site.  [PMID:8647296]

3. Hughes, Francis M and 10 more authors.  2010-06-24  Identification and functional characterization of a stable, centrally active derivative of the neurotensin (8-13) fragment as a potential first-in-class analgesic.  [PMID:20481538]

4. Fanelli, Roberto R and 9 more authors.  2017-04-27  Use of Molecular Modeling to Design Selective NTS2 Neurotensin Analogues.  [PMID:28368584]

5. Keller, Max and 10 more authors.  2020-01-09  Fluorescence Labeling of Neurotensin(8-13) via Arginine Residues Gives Molecular Tools with High Receptor Affinity.  [PMID:31938457]

6. Chartier, Magali and 6 more authors.  2021-02-25  Design, Structural Optimization, and Characterization of the First Selective Macrocyclic Neurotensin Receptor Type 2 Non-opioid Analgesic.  [PMID:33538583]

Source

Source(1):

• Scientific Literature