Dihydrostreptomycin

Details

• Internal ID: f2d79430-180b-460c-97a7-564f1d987206
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides > Aminocyclitol glycosides
• IUPAC Name: 2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine
• InChI: InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
• InChI Key: ASXBYYWOLISCLQ-HZYVHMACSA-N
• Popularity: 2,506 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₄₁N₇O₁₂
• Molecular Weight: 583.60 g/mol
• Exact Mass: 583.28131977 g/mol
• Topological Polar Surface Area (TPSA): 340.00 Ų
• XlogP: -8.20
• Atomic LogP (AlogP): -8.37
• H-Bond Acceptor: 15
• H-Bond Donor: 13
• Rotatable Bonds: 9

Synonyms

• Vibriomycin
• DHMS
• Dihydrostreptomycine
• Streptomycin, dihydro-
• Dihidroestreptomicina
• Diidrostreptomicina
• Dihydrostreptomycinum
• P2I6R8W6UA
• CHEBI:38291
• N,N'''-[(1R,2R,3S,4R,5R,6S)-4-({5-deoxy-2-O-[2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl]-3-C-(hydroxymethyl)-alpha-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine
• 2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine
• 1,1'-[(1R,2R,3S,4R,5R,6S)-4-({5-deoxy-2-O-[2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl]-3-C-(hydroxymethyl)-alpha-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine
• 1,1'-((1R,2R,3S,4R,5R,6S)-4-((5-deoxy-2-O-(2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl)-3-C-(hydroxymethyl)-alpha-L-lyxofuranosyl)oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine
• 2-((1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-((2R,3R,4R,5S)-3-((2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl)oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl)oxy-2,5,6-trihydroxycyclohexyl)guanidine
• N,N'''-((1R,2R,3S,4R,5R,6S)-4-((5-deoxy-2-O-(2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl)-3-C-(hydroxymethyl)-alpha-L-lyxofuranosyl)oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine
• RefChem:133946
• DTXCID702937
• S01AA15
• 204-888-2
• 128-46-1
• Dihydrostreptomycin
• DTXSID0022937
• Dihydrostreptomycin (INN)
• DIHYDROSTREPTOMYCIN [INN]
• C21H41N7O12
• UNII-P2I6R8W6UA
• Diidrostreptomicina [DCIT]
• Dihydrostreptomycin [INN:BAN]
• Dihydrostreptomycine [INN-French]
• Dihydrostreptomycinum [INN-Latin]
• Dihidroestreptomicina [INN-Spanish]
• EINECS 204-888-2
• NSC402956
• DIHYDROSTREPTOMYCIN [MI]
• CHEMBL1950576
• GTPL12163
• ASXBYYWOLISCLQ-HZYVHMACSA-N
• DIHYDROSTREPTOMYCIN [WHO-DD]
• DB11512
• 2,4-Diguanidino-3,5,6-trihydroxycyclohexyl-5-deoxy-2-O-(2-deoxy-2-methylamino-alpha-L-glucopyranosyl)-3-hydroxymethyl-beta-L-lyxo-pentanofuranoside
• C01023
• D07840
• 128D461
• 1-[(1S,2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyl-tetrahydrofuran-2-yl]oxy-5-guanidino-3,4,6-trihydroxy-cyclohexyl]guanidine
• 2-[(1S,2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydropyran-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyl-tetrahydrofuran-2-yl]oxy-5-guanidino-3,4,6-trihydroxy-cyclohexyl]guanidine
• 71R
• D-Streptamine, O-2-deoxy-2-(methylamino)-.alpha.-L-glucopyranosyl-(1->2)-O-5-deoxy-3-C-(hydroxymethyl)-.alpha.-L-lyxofuranosyl-(1->4)-N,N'-bis(aminoiminomethyl)
• D-STREPTAMINE, O-2-DEOXY-2-(METHYLAMINO)-.ALPHA.-L-GLUCOPYRANOSYL-(1->2)-O-5-DEOXY-3-C-(HYDROXYMETHYL)-.ALPHA.-L-LYXOFURANOSYL-(1->4)-N1,N3-BIS(AMINOIMINOMETHYL)-
• N,N'''-[(1R,2R,3S,4R,5R,6S)-4-({5-deoxy-2-O-[2-deoxy-2-(methylamino)-a-L-glucopyranosyl]-3-C-(hydroxymethyl)-a-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine
• Streptamine, O-beta-D-mannopyranosyl-(1-4)-2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl-(1-2)-5-deoxy-O-3-C-(hydroxymethyl)-alpha-L-lyxofuranosyl-(1-4)-N,N'-diamidino-, D-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9601	96.01%
Caco-2	-	0.8599	85.99%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Lysosomes	0.6388	63.88%
OATP2B1 inhibitior	-	0.7303	73.03%
OATP1B1 inhibitior	+	0.9242	92.42%
OATP1B3 inhibitior	+	0.9482	94.82%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9051	90.51%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.5822	58.22%
CYP3A4 substrate	+	0.6257	62.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8216	82.16%
CYP3A4 inhibition	-	0.9442	94.42%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.6656	66.56%
CYP inhibitory promiscuity	-	0.9250	92.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5793	57.93%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9347	93.47%
Skin irritation	-	0.7779	77.79%
Skin corrosion	-	0.9213	92.13%
Ames mutagenesis	+	0.6646	66.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.4662	46.62%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	-	0.8226	82.26%
skin sensitisation	+	0.6952	69.52%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6544	65.44%
Acute Oral Toxicity (c)	III	0.5380	53.80%
Estrogen receptor binding	+	0.6522	65.22%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.6055	60.55%
Glucocorticoid receptor binding	+	0.5376	53.76%
Aromatase binding	+	0.6865	68.65%
PPAR gamma	+	0.6472	64.72%
Honey bee toxicity	-	0.6605	66.05%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.9174	91.74%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	398.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.34%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.88%	96.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	96.08%	95.58%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.81%	96.61%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.91%	83.57%
CHEMBL299	P17252	Protein kinase C alpha	90.30%	98.03%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.86%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	88.88%	95.93%
CHEMBL2996	Q05655	Protein kinase C delta	88.84%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.44%	97.09%
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	85.59%	97.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.47%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	83.86%	97.88%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	83.43%	92.32%
CHEMBL2581	P07339	Cathepsin D	83.39%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.83%	95.83%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.47%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.64%	95.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.14%	92.88%

Plants that contains it

• Pinus massoniana

Cross-Links

• PubChem: 439369
• NPASS: NPC57436
• LOTUS: LTS0158133
• wikiData: Q3707637