NOVOBIOCIN SODIUM

ID: ALA3183453

Cas Number: 1476-53-5

PubChem CID: 23663939

Max Phase: Approved

First Approval: 1964

Molecular Formula: C31H35N2NaO11

Molecular Weight: 612.63

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Novobiocin monosodium salt | Novobiocin sodium | Novobiocin, monosodium salt | Sodium novobiocin | NSC-2382 | NOVOBIOCIN SODIUM|Albamycin|Albadry|Sodium novobiocin|Cathomycin|Inabiocin|Novobiocin, monosodium salt|Drygard/Biodry|Sodium albamycin|Novobiocin natrium|Novobiocina Bomaca|Novobiocin monosodium salt|Albamycin (capsule)|Monosodium novobiocin|Novobiocin monosodium|Cardelmycin sodium salt|PA 93 Na salt|Streptonivicin sodium salt|UNII-Q9S9NQ5YIY|Novobiocin, sodium deriv.|Q9S9NQ5YIY|1476-53-Show More⌵

Trade Names(3): Albamycin | Spheromycin | Vulcamycin

Canonical SMILES:  CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](Oc2ccc3c([O-])c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2C)OC1(C)C.[Na+]

Standard InChI:  InChI=1S/C31H36N2O11.Na/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29;/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q;+1/p-1/t23-,25+,26-,29-;/m1./s1

Standard InChI Key:  WWPRGAYLRGSOSU-RNROJPEYSA-M

Molfile:  

     RDKit          2D

 45 47  0  0  0  0  0  0  0  0999 V2000
    6.5272    2.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062    2.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951    1.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5272    1.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951    2.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062    1.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -0.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2578   -0.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2285    2.8769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355   -0.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8059   -1.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9545    2.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6579    1.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5862    1.0447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492   -1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6657    2.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    2.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0978    2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3867    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062    3.6968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5499    2.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2285    1.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6579    2.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0880    3.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9545    1.6374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8140    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604   -0.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2512    2.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6608    3.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3768    4.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9245   -0.0715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3864   -1.7160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023   -2.5408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7992    4.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058   -1.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4305   -2.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2364    1.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8981    2.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120   -2.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7483    0.9710    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  2  1  2  0
  3  7  1  0
  4  1  1  0
  5  9  1  0
  6  2  1  0
  7  4  1  0
  8 17  1  1
  9  8  1  0
 10  1  1  0
 11  8  1  0
 12 13  1  0
 13 11  1  0
 14  3  1  0
 15 10  1  0
 16 14  2  0
 17 16  1  0
  5 18  1  6
 19 18  1  0
 20 15  1  0
 21  6  1  0
 22 23  1  0
 23 20  2  0
 24  2  1  0
 25 30  1  0
 26  4  2  0
 27 21  2  0
 28 34  1  0
 29 15  2  0
 30 22  1  0
 31 19  2  0
 32 25  2  0
 33 20  1  0
 34 33  2  0
  9 35  1  6
 36 19  1  0
 12 37  1  1
 38 28  1  0
 39 13  1  0
 40 13  1  0
 41 14  1  0
 42 32  1  0
 43 32  1  0
 44 37  1  0
  3  6  2  0
 16 27  1  0
 22 28  2  0
  5 12  1  0
M  CHG  2  24  -1  45   1
M  END

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 612.63

Molecular Weight (Monoisotopic): 612.2319

AlogP: 3.63

#Rotatable Bonds: 8

Polar Surface Area: 200.01

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 5.51

CX Basic pKa: ┄

CX LogP: 3.26

CX LogD: 1.36

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.18

Np Likeness Score: 1.39

References

1. Unpublished dataset, 

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Unpublished dataset, 

7. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

8. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

9. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

10. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

11. Unpublished dataset, 

Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• Withdrawn Drugs
• SARS-CoV-2 Screening Data 2020-21