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(3R,4S,5S,7R,9E,11R,12S)-12-((1R)-1-Hydroxyethyl)-3,5,7,11-tetramethyl-4-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)oxacyclododec-9-ene-2,8-dione

HCID 5282033
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Basic information

CAS
497-73-4
Standard SMILES
C[C@@H]1C[C@H](N(C)C)[C@@H](O)[C@H](O[C@H]2[C@@H](C)C[C@@H](C)C(=O)/C=C/[C@@H](C)[C@@H]([C@@H](C)O)OC(=O)[C@@H]2C)O1
InChIKey
UEIVQYHYALXCBD-OTUJEKPESA-N
Molecular formula
C25H43NO7
Average molar mass
469.6 g/mol
Monoisotopic mass
469.30395271

Overview

Neomethymycin is a macrolide antibiotic, an enone and a monosaccharide derivative. It has a role as a bacterial metabolite. It is a conjugate base of a neomethymycin(1+).

Names & identifiers

Preferred name
(3R,4S,5S,7R,9E,11R,12S)-12-((1R)-1-Hydroxyethyl)-3,5,7,11-tetramethyl-4-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)oxacyclododec-9-ene-2,8-dione
IUPAC
(3R,4S,5S,7R,9E,11R,12S)-4-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-12-[(1R)-1-hydroxyethyl]-3,5,7,11-tetramethyl-1-oxacyclododec-9-ene-2,8-dione
English name
neomethymycin
Molecular formula
C25H43NO7
Molecular weight
469.61

Names & synonyms

Neomethymycin497-73-42BSX67J222CHEBI:29656DTXSID201026558(3R,4S,5S,7R,9E,11R,12S)-4-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-12-[(1R)-1-hydroxyethyl]-3,5,7,11-tetramethyl-1-oxacyclododec-9-ene-2,8-dione(3R,4S,5S,7R,9E,11R,12S)-4-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-12-((1R)-1-hydroxyethyl)-3,5,7,11-tetramethyl-1-oxacyclododec-9-ene-2,8-dioneRefChem:906040DTXCID801510721(3R,4S,5S,7R,9E,11R,12S)-12-((1R)-1-Hydroxyethyl)-3,5,7,11-tetramethyl-4-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)oxacyclododec-9-ene-2,8-dioneUNII-2BSX67J222Methymycin, 10-deoxy-12-hydroxy-, (12R)-
Show more names
Oxacyclododec-9-ene-2,8-dione, 12-[(1R)-1-hydroxyethyl]-3,5,7,11-tetramethyl-4-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, (3R,4S,5S,7R,9E,11R,12S)-
(12R)-10-Deoxy-12-hydroxymethymycinNEOMETHYMYCIN [MI]SCHEMBL652365CHEMBL521954orb1991914LMPK04000036AKOS040734840T124771

Database identifiers

CAS
497-73-4
PubChem CID
5282033
DTXSID
DTXSID201026558
ChEMBL
CHEMBL521954
ChEBI
CHEBI:29656
UNII
2BSX67J222
Nikkaji
J1.085.773B

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
106 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
4
Heavy atoms
33
Formal charge
0
Complexity
696

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Macrolides and lactone polyketides [PK04]

Physicochemical properties

Melting point
156 · 156-158°
alpha
25 · D25 +93°
Boiling point
627.8 · 627.8±55.0 °C(Predicted)
Density
1.13 · 1.13±0.1 g/cm3(Predicted)
pka
13.46 · 13.46±0.70(Predicted)
FDA UNII
2 BSX67J222 · 2BSX67J222

Chemistry & industry

Additional notes

DefinitionChEBI: A twelve-membered macrolide antibiotic that is biosynthesised by Streptomyces venezuelae.

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