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2-((3-Amino-6-((3-amino-6-((3,6-diamino-1-hydroxyhexylidene)amino)-1-hydroxyhexylidene)amino)-1-hydroxyhexylidene)amino)-2-deoxy-N-(4,7-dihydroxy-3a,6,7,7a-tetrahydro-3H-imidazo(4,5-c)pyridin-2-yl)-4-O-(hydroxy(imino)methyl)hexopyranosylamine

HCID 199159
NotesReactions
Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
3776-37-2
Standard SMILES
NCCC[C@H](N)CC(=O)NCCC[C@H](N)CC(=O)NCCC[C@H](N)CC(=O)N[C@@H]1[C@H](O)[C@@H](OC(N)=O)[C@@H](CO)O[C@H]1NC1=NC2C(=O)NCC(O)C2N1
InChIKey
WUJTXMVGXDQPNN-RPRJZONPSA-N
Molecular formula
C31H58N12O10
Average molar mass
758.9 g/mol
Monoisotopic mass
758.43988609

Overview

streptothricin D has been reported in Streptomyces qinlingensis, Streptomyces, and Streptomyces nojiriensis with data available.

Names & identifiers

Preferred name
2-((3-Amino-6-((3-amino-6-((3,6-diamino-1-hydroxyhexylidene)amino)-1-hydroxyhexylidene)amino)-1-hydroxyhexylidene)amino)-2-deoxy-N-(4,7-dihydroxy-3a,6,7,7a-tetrahydro-3H-imidazo(4,5-c)pyridin-2-yl)-4-O-(hydroxy(imino)methyl)hexopyranosylamine
IUPAC
[(2R,3R,4S,5R,6R)-5-[[(3S)-3-amino-6-[[(3S)-3-amino-6-[[(3S)-3,6-diaminohexanoyl]amino]hexanoyl]amino]hexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)-6-[(7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl)amino]oxan-3-yl] carbamate
English name
streptothricin D
Molecular formula
C31H58N12O10
Molecular weight
758.88

Names & synonyms

[(2R,3R,4S,5R,6R)-5-[[(3S)-3-amino-6-[[(3S)-3-amino-6-[[(3S)-3,6-diaminohexanoyl]amino]hexanoyl]amino]hexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)-6-[(7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl)amino]oxan-3-yl] carbamateDTXSID60958811((2R,3R,4S,5R,6R)-5-(((3S)-3-amino-6-(((3S)-3-amino-6-(((3S)-3,6-diaminohexanoyl)amino)hexanoyl)amino)hexanoyl)amino)-4-hydroxy-2-(hydroxymethyl)-6-((7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo(4,5-c)pyridin-2-yl)amino)oxan-3-yl) carbamateRefChem:1060505DTXCID501386705((2R,3R,4S,5R,6R)-5-(((3S)-3-amino-6-(((3S)-3-amino-6-(((3S)-3,6-diaminohexanoyl)amino)hexanoyl)amino)hexanoyl)amino)-4-hydroxy-2-(hydroxymethyl)-6-((E)-(7-hydroxy-4-oxo-3,3a,5,6,7,7a-hexahydro-1H-imidazo(4,5-c)pyridin-2-ylidene)amino)oxan-3-yl) carbamate2-((3-Amino-6-((3-amino-6-((3,6-diamino-1-hydroxyhexylidene)amino)-1-hydroxyhexylidene)amino)-1-hydroxyhexylidene)amino)-2-deoxy-N-(4,7-dihydroxy-3a,6,7,7a-tetrahydro-3H-imidazo(4,5-c)pyridin-2-yl)-4-O-(hydroxy(imino)methyl)hexopyranosylamine

Properties

Computed structural properties

XLogP
-7.3
Topological polar surface area
379 Ų
Hydrogen bond donors
14
Hydrogen bond acceptors
15
Rotatable bonds
23
Heavy atoms
53
Formal charge
0
Complexity
1,260

Physicochemical properties

Density
1.67 · 1.67±0.1 g/cm3(Predicted)
pka
12.62 · 12.62±0.70(Predicted)

Chemistry & industry

Applications · 2 items

DescriptionRacemomycin B is a beta-lysine rich streptothricin antibiotic.

UsesRacemomycin B (229-B; Streptothricin D), the main component from Streptomyces lavendulae OP-2, is a streptothricin antibiotic containing three β-lysine groups. RM-B exhibits antimicrobial activity against plant pathogenic microorganisms and effectively inhibits the growth of Brassica rapa L. roots at 50 ppm. RM-B showed a minimum inhibitory concentration (MIC) of 0.4 μg/ml against Pseudomonas syringae pv. tabaci IFO-3508 and a MIC range of 0.1-2.0 μg/ml against six strains of Fusarium oxysporum, showing stronger antimicrobial activity than RM-A and RM-C. The biological activity of racemomycin compounds increases with the increase in the number of β-lysine groups.

Suppliers3 total

上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
Streptothricin D
Antibiotic OP 2C
BRN 4288011
4H-Imidazo(4,5-c)pyridin-4-one, 2-((2-(3-amino-6-(3-amino-6-(3,6-diaminohexanamido)hexanamido)hexanamido)-2-deoxy-beta-D-gulopyranosyl)amino)-3,3a,5,6,7,7a-hexahydro-7-hydroxy-, 6'-carbamate
SCHEMBL29884512
Show more names
Racemomycin B4H-Imidazo[4,5-c]pyridin-4-one, 2-[[2-[[(3S)-3-amino-6-[[(3S)-3-amino-6-[[(3S)-3,6-diamino-1-oxohexyl]amino]-1-oxohexyl]amino]-1-oxohexyl]amino]-4-O-(aminocarbonyl)-2-deoxy-β-D-gulopyranosyl]amino]-1,3a,5,6,7,7a-hexahydro-7-hydroxy-, (3aS,7R,7aS)-

Database identifiers

CAS
3776-37-2
PubChem CID
199159