(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 tert-butyl ester

ID: ALA325278

PubChem CID: 44341870

Max Phase: Preclinical

Molecular Formula: C32H49N5O10

Molecular Weight: 663.77

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)OC(C)(C)C)[C@@H](O)[C@H]3O)c2=O)cc1

Standard InChI:  InChI=1S/C32H49N5O10/c1-18(2)16-21(33)28(42)35-14-7-13-34-23(30(43)47-32(3,4)5)24(39)27-25(40)26(41)29(46-27)36-15-12-22(38)37(31(36)44)17-19-8-10-20(45-6)11-9-19/h8-12,15,18,21,23-27,29,34,39-41H,7,13-14,16-17,33H2,1-6H3,(H,35,42)/t21-,23+,24-,25+,26-,27?,29-/m1/s1

Standard InChI Key:  GBWUIAXBZNFBGW-ODJVACDSSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA325278

   tert-butyl (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-hydroxypropanoate

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: 663.77

Molecular Weight (Monoisotopic): 663.3479

AlogP: -0.77

#Rotatable Bonds: 15

Polar Surface Area: 216.60

Molecular Species: NEUTRAL

HBA: 14

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.47

CX Basic pKa: 8.43

CX LogP: -0.06

CX LogD: -1.14

Aromatic Rings: 2

Heavy Atoms: 47

QED Weighted: 0.10

Np Likeness Score: 0.19

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