(E)-3-[4-((2S,3S,4S,5S)-5-Acetyl-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-3-hydroxy-phenyl]-2-methyl-N-((3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxy-hexahydro-benzo[1,3]dioxol-5-yl)-acrylamide

ID: ALA267436

Chembl Id: CHEMBL267436

Cas Number: 6379-56-2

PubChem CID: 6433481

Max Phase: Preclinical

Molecular Formula: C23H29NO12

Molecular Weight: 511.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)[C@H]1O[C@@H](Oc2ccc(/C=C(\C)C(=O)N[C@@H]3[C@H](O)[C@@H](O)[C@H]4OCO[C@H]4[C@@H]3O)cc2O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C23H29NO12/c1-8(22(32)24-13-14(27)16(29)21-20(15(13)28)33-7-34-21)5-10-3-4-12(11(26)6-10)35-23-18(31)17(30)19(36-23)9(2)25/h3-6,13-21,23,26-31H,7H2,1-2H3,(H,24,32)/b8-5+/t13-,14+,15-,16-,17+,18+,19-,20+,21-,23-/m1/s1

Standard InChI Key:  YQYJSBFKSSDGFO-IIHALWDASA-N

Alternative Forms

1. Parent:

   

   ALA267436

   HYGROMYCIN A

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: 511.48

Molecular Weight (Monoisotopic): 511.1690

AlogP: -2.47

#Rotatable Bonds: 6

Polar Surface Area: 204.47

Molecular Species: NEUTRAL

HBA: 12

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.66

CX Basic pKa: ┄

CX LogP: -1.69

CX LogD: -1.69

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: 1.35

References

1. Hecker SJ, Lilley SC, Minich ML, Werner KM.  (1992)  Semisynthetic modification of hygromycin A. 3. synthesis and antibacterial activity of aminocyclitol analogs.,  2  (9): [10.1016/S0960-894X(00)80609-5]

2. Hecker SJ, Lilley SC, Werner KM.  (1992)  Hygromycin A: preparation of aminocyclitol analogs defining the minimum functionality required for biological activity,  2  (9): [10.1016/S0960-894X(00)80615-0]

3. Jaynes BH, Cooper CB, Hecker SJ, Blair KT, Elliott NC, Lilley SC, Minich ML, Schicho DL, Werner KM.  (1993)  Synthesis and vitro antibacterial activity of hygromycin a analogs modified at the C4 aryl position,  3  (8): [10.1016/S0960-894X(00)80012-8]

4. Hecker SJ, Cooper CB, Blair KT, Lilley SC, Minich ML, Werner KM.  (1993)  Semisynthetic modification of hygromycin A. 2. synthesis and antibacterial activity of aryl analogs.,  3  (2): [10.1016/S0960-894X(01)80895-7]

5. Hecker SJ, Lilley SC, Minich ML, Werner KM.  (1993)  Application of hygromycin a structure activity relationships to the antibiotic A201A.,  3  (2): [10.1016/S0960-894X(01)80896-9]

6. Hecker SJ, Minich ML, Werner KM.  (1992)  Semisynthetic modification of hygromycin A. 1. Synthesis and antibacterial activity of vinyl methyl and amide analogs.,  2  (6): [10.1016/S0960-894X(01)81192-6]

7. Visser MS, Freeman-Cook KD, Brickner SJ, Brighty KE, Le PT, Wade SK, Monahan R, Martinelli GJ, Blair KT, Moore DE..  (2010)  Synthesis and biological evaluation of novel hygromycin A antibacterial agents.,  20  (22): [PMID:20864341] [10.1016/j.bmcl.2010.08.139]

8. Dhote V, Starosta AL, Wilson DN, Reynolds KA..  (2009)  The final step of hygromycin A biosynthesis, oxidation of C-5''-dihydrohygromycin A, is linked to a putative proton gradient-dependent efflux.,  53  (12): [PMID:19770276] [10.1128/aac.01069-09]

Source

Source(1):

• Scientific Literature