(2S,5S,6S)-2-((R)-(((2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-6-(((R)-3-(((R)-4-carboxy-3-methylbutanoyl)oxy)tridecanoyl)oxy)-1,4-dimethyl-3-oxo-1,4-diazepane-5-carboxylic acid

ID: ALA5280571

Max Phase: Preclinical

Molecular Formula: C41H65N5O18

Molecular Weight: 915.99

Names and Identifiers

Canonical SMILES:  CCCCCCCCCC[C@H](CC(=O)O[C@H]1CN(C)[C@@H](C(O[C@@H]2O[C@H](CN)[C@@H](O)[C@H]2O)[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)C(=O)N(C)[C@@H]1C(=O)O)OC(=O)C[C@H](C)CC(=O)O

Standard InChI:  InChI=1S/C41H65N5O18/c1-5-6-7-8-9-10-11-12-13-22(60-27(50)17-21(2)16-26(48)49)18-28(51)61-24-20-44(3)30(37(56)45(4)29(24)39(57)58)35(64-40-34(55)31(52)23(19-42)62-40)36-32(53)33(54)38(63-36)46-15-14-25(47)43-41(46)59/h14-15,21-24,29-36,38,40,52-55H,5-13,16-20,42H2,1-4H3,(H,48,49)(H,57,58)(H,43,47,59)/t21-,22-,23-,24+,29+,30+,31-,32+,33-,34-,35?,36+,38-,40+/m1/s1

Standard InChI Key:  VVLFISHNJLAURF-TVZWZLRASA-N

Molfile:  

 
     RDKit          2D

 65 68  0  0  0  0  0  0  0  0999 V2000
    0.3882   -4.4478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0993   -4.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213   -5.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -5.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2293   -4.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -4.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100   -5.3649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -5.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -5.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7363   -5.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070   -4.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7869   -4.4237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906   -3.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9877   -4.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4510   -5.7557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -6.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -3.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -3.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982   -3.1879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -2.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4446   -2.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7451   -2.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6512   -3.3953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   -3.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4446   -1.3081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299   -0.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299   -0.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    0.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    1.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4446    2.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4446    3.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593    4.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593    4.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8740    5.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8740    6.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5887    6.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995   -0.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4141    0.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1289   -0.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436    0.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5583   -0.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2730    0.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9877   -0.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2730    1.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436    1.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4141    1.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152   -1.3081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8119   -1.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090   -2.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5983   -1.0296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3236   -3.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4721   -4.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -4.3968    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124   -6.4660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5049   -6.2553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -4.4534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -3.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5287   -3.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -3.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -4.4535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5287   -4.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5287   -5.6914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581   -3.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  0
  1  5  1  0
  5  6  1  1
  6  7  1  0
  8  7  1  1
  9  8  1  0
  9 10  1  0
 10 11  1  0
 12 11  1  0
  8 12  1  0
 11 13  1  1
 13 14  1  0
 10 15  1  6
  9 16  1  6
  6 17  1  0
 18 17  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 23 22  1  0
 17 23  1  0
 23 24  1  0
 21 25  1  1
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 28 39  1  1
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 44 46  2  0
 42 47  1  6
 40 48  2  0
 26 49  2  0
 20 50  1  6
 50 51  1  0
 50 52  2  0
 19 53  1  0
 18 54  2  0
 17 55  1  6
  4 56  1  6
  3 57  1  6
  2 58  1  1
 59 58  1  0
 60 59  2  0
 61 60  1  0
 62 61  1  0
 63 62  1  0
 58 63  1  0
 63 64  2  0
 61 65  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280571

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 915.99

Molecular Weight (Monoisotopic): 915.4325

AlogP: -1.58

#Rotatable Bonds: 24

Polar Surface Area: 340.24

Molecular Species: ZWITTERION

HBA: 19

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 23

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.06

CX Basic pKa: 8.75

CX LogP: -4.78

CX LogD: -5.46

Aromatic Rings: 1

Heavy Atoms: 64

QED Weighted: 0.04

Np Likeness Score: 1.27

References

1. Serpi M, Ferrari V, Pertusati F..  (2016)  Nucleoside Derived Antibiotics to Fight Microbial Drug Resistance: New Utilities for an Established Class of Drugs?,  59  (23): [PMID:27607900] [10.1021/acs.jmedchem.6b00325]

Source

Source(1):

• Scientific Literature