(2S,3R)-2-[3-((R)-2-Benzyloxycarbonylamino-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: ALA114703

PubChem CID: 44341869

Max Phase: Preclinical

Molecular Formula: C36H47N5O12

Molecular Weight: 741.79

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](CC(C)C)NC(=O)OCc4ccccc4)C(=O)O)[C@@H](O)[C@H]3O)c2=O)cc1

Standard InChI:  InChI=1S/C36H47N5O12/c1-21(2)18-25(39-35(49)52-20-23-8-5-4-6-9-23)32(46)38-16-7-15-37-27(34(47)48)28(43)31-29(44)30(45)33(53-31)40-17-14-26(42)41(36(40)50)19-22-10-12-24(51-3)13-11-22/h4-6,8-14,17,21,25,27-31,33,37,43-45H,7,15-16,18-20H2,1-3H3,(H,38,46)(H,39,49)(H,47,48)/t25-,27+,28-,29+,30-,31?,33-/m1/s1

Standard InChI Key:  OENLDZSIJHMDKM-YMAKLAJDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA114703

   (2S,3R)-3-[(3S,4R,5R)-3,4-dihydroxy-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-3-hydroxy-2-[3-[[(2R)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propylamino]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: 741.79

Molecular Weight (Monoisotopic): 741.3221

AlogP: -0.06

#Rotatable Bonds: 18

Polar Surface Area: 239.91

Molecular Species: ZWITTERION

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.27

CX Basic pKa: 9.53

CX LogP: -1.57

CX LogD: -1.57

Aromatic Rings: 3

Heavy Atoms: 53

QED Weighted: 0.08

Np Likeness Score: -0.01

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