2-Amino-3,6-anhydro-2,4,5,7-tetradeoxy-L-xylo-hept-4-enonic acid
Basic information
- CAS
18455-25-9- Standard SMILES
C[C@H]1C=C[C@H]([C@H](N)C(=O)O)O1- InChIKey
PNOKUGWGMLEAPE-JKUQZMGJSA-N- Molecular formula
- C7H11NO3
- Average molar mass
- 157.17 g/mol
- Monoisotopic mass
- 157.07389321
Overview
Furanomycin is a non-proteinogenic L-alpha-amino acid that is L-alanine in which the methyl group is replaced by a (2R,5S)-5-methyl-2,5-dihydrofuran-2-yl moiety. It has a role as an antimicrobial agent, an antibacterial agent and a bacterial metabolite. It is a dihydrofuran and a non-proteinogenic L-alpha-amino acid.
Names & identifiers
- Preferred name
- 2-Amino-3,6-anhydro-2,4,5,7-tetradeoxy-L-xylo-hept-4-enonic acid
- IUPAC
- (2S)-2-amino-2-[(2R,5S)-5-methyl-2,5-dihydrofuran-2-yl]acetic acid
- English name
- furanomycin
- Molecular formula
- C7H11NO3
- Molecular weight
- 157.17
Names & synonyms
Furanomycin18455-25-9(+)-furanomycin(2S)-2-amino-2-[(2R,5S)-5-methyl-2,5-dihydrofuran-2-yl]acetic acidL-xylo-Hept-4-enonic acid, 2-amino-3,6-anhydro-2,4,5,7-tetradeoxy-218WD6K9H0CHEBI:79390NSC-1163282-AMINO-3,6-ANHYDRO-2,4,5,7-TETRADEOXY-L-XYLO-HEPT-4-ENONIC ACID(2S)-2-amino-2-((2R,5S)-5-methyl-2,5-dihydrofuran-2-yl)acetic acidRefChem:141763L-(+)-furanomycin
Show more names
(αS,2R,5S)-α-Amino-5-methyl-2,5-dihydrofuran-2-acetic acid(5S,2R,αS)-α-Amino-2,5-dihydro-5-methyl-2-furanacetic acid
(6S)-2-amino-3,6-anhydro-2,4,5-trideoxy-6-methyl-D-threo-hex-4-enonic acidFuronamycinUNII-218WD6K9H0orb1986028SCHEMBL29885117DTXSID301028838(S)-2-amino-2-((2R,5S)-5-methyl-2,5-dihydrofuran-2-yl)acetic acidAKOS040751877
Database identifiers
- CAS
18455-25-9
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 72.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 190
Physicochemical properties
- Melting point
- 221 · 221-224 °C(Solv: water (7732-18-5); acetone (67-64-1))
- Boiling point
- 305.6 · 305.6±37.0 °C(Predicted)
- Density
- 1.238 · 1.238±0.06 g/cm3(Predicted)
- pka
- 1.9 · 1.90±0.10(Predicted)
- FDA UNII
- 218 WD6K9H0 · 218WD6K9H0
Chemistry & industry
Additional notes
DefinitionChEBI: A non-proteinogenic L-alpha-amino acid that is L-alanine in which the methyl group is replaced by a (2R,5S)-5-methyl-2,5-dihydrofuran-2-yl moiety.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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