SID11532875

ID: ALA1237072

Chembl Id: CHEMBL1237072

Max Phase: Approved

First Approval: 1995

Molecular Formula: C42H78N2O14

Molecular Weight: 835.09

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dirithromycin | LY 237216 | LY-237216 | NSC-758672

Trade Names(1): Dynabac

Canonical SMILES:  CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)[C@@H]2N[C@@H](COCCOC)O[C@H]([C@H]2C)[C@]1(C)O

Standard InChI:  InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1

Standard InChI Key:  WLOHNSSYAXHWNR-DWIOZXRMSA-N

Alternative Forms

1. Parent:

   

   ALA1237072

   DIRITHROMYCIN

Molecule Features

Natural Product: Yes

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: Yes

Calculated Properties

Molecular Weight: 835.09

Molecular Weight (Monoisotopic): 834.5453

AlogP: 2.20

#Rotatable Bonds: 12

Polar Surface Area: 196.33

Molecular Species: BASE

HBA: 16

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.48

CX Basic pKa: 13.48

CX LogP: 2.95

CX LogD: 0.46

Aromatic Rings: ┄

Heavy Atoms: 58

QED Weighted: 0.14

Np Likeness Score: 1.41

References

1. PubChem BioAssay data set, 

2. Unpublished dataset, 

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

4. PubChem BioAssay data set, 

5. WHO Anatomical Therapeutic Chemical Classification, 

6. Iwata M, Hirose L, Kohara H, Liao J, Sawada R, Akiyoshi S, Tani K, Yamanishi Y..  (2018)  Pathway-Based Drug Repositioning for Cancers: Computational Prediction and Experimental Validation.,  61  (21): [PMID:30371064] [10.1021/acs.jmedchem.8b01044]

7. Unpublished dataset, 

8. 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]

9. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

10. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(8):

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