(2S,3R)-2-[3-((R)-2-Amino-4-methyl-pentanoylamino)-propylamino]-3-{(3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid

ID: ALA116005

PubChem CID: 44341868

Max Phase: Preclinical

Molecular Formula: C28H41N5O10

Molecular Weight: 607.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2c(=O)ccn([C@@H]3OC([C@H](O)[C@H](NCCCNC(=O)[C@H](N)CC(C)C)C(=O)O)[C@@H](O)[C@H]3O)c2=O)cc1

Standard InChI:  InChI=1S/C28H41N5O10/c1-15(2)13-18(29)25(38)31-11-4-10-30-20(27(39)40)21(35)24-22(36)23(37)26(43-24)32-12-9-19(34)33(28(32)41)14-16-5-7-17(42-3)8-6-16/h5-9,12,15,18,20-24,26,30,35-37H,4,10-11,13-14,29H2,1-3H3,(H,31,38)(H,39,40)/t18-,20+,21-,22+,23-,24?,26-/m1/s1

Standard InChI Key:  BGVQBEFPHLWZDB-PHHZKTJJSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA116005

   (2S,3R)-2-[3-[[(2R)-2-amino-4-methylpentanoyl]amino]propylamino]-3-[(3S,4R,5R)-3,4-dihydroxy-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-3-hydroxypropanoic 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: 607.66

Molecular Weight (Monoisotopic): 607.2853

AlogP: -2.03

#Rotatable Bonds: 15

Polar Surface Area: 227.60

Molecular Species: ZWITTERION

HBA: 13

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.06

CX Basic pKa: 9.53

CX LogP: -3.88

CX LogD: -4.75

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.11

Np Likeness Score: 0.23

References

1. Yamashita A, Norton E, Petersen PJ, Rasmussen BA, Singh G, Yang Y, Mansour TS, Ho DM..  (2003)  Muraymycins, novel peptidoglycan biosynthesis inhibitors: synthesis and SAR of their analogues.,  13  (19): [PMID:12951123] [10.1016/s0960-894x(03)00671-1]

Source

Source(1):

• Scientific Literature