Streptonigrin

Details

• Internal ID: e2e88a2d-1bf4-4281-bafa-efd504705ed6
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Bipyridines and oligopyridines
• IUPAC Name: 5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid
• InChI: InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)
• InChI Key: PVYJZLYGTZKPJE-UHFFFAOYSA-N
• Popularity: 423 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₂N₄O₈
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.14376367 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• Bruneomycin
• Rufocromomycin
• Nigrin
• 3930-19-6
• Streptonigran
• Rufocromomycine
• Valacidin
• NSC-45383
• Rufocromomicina
• Rufocromomycinum
• Abbott Crystalline antibiotic
• Streptonigrin [USAN]
• NSC 45383
• NSC45383
• Antibiotic from Streptomyces flocculus
• Rufochromomycin
• A 050165L302
• Streptonigrin (racemate)
• AO50165L302
• NSC83950
• 2-Pyridinecarboxylic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-
• NSC-83950
• CHEBI:9287
• MLS000028827
• 5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid
• Rufocromomycin [INN]
• 5278 R. P.
• SMR000058748
• MLS000766205
• MLS000766219
• Picolinic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-
• 3930-19-6 (R-isomer)
• 1079893-79-0 (racemate)
• NSC-56748
• 261Q3JB310
• 1079893-79-0
• Rufocromomycin (INN)
• Streptonigrin (USAN)
• 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid
• SN (VAN)
• 5-Amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid
• Rufocromomycine [INN-French]
• Rufocromomycinum [INN-Latin]
• Rufocromomicina [INN-Spanish]
• CCRIS 1264
• SR-01000721857
• EINECS 223-501-8
• NSC 83950
• BRN 0599390
• AI3-52152
• UNII-261Q3JB310
• WLN: T66 BV EV GNJ CO1 DZ H- BT6NJ CZ DR BQ CO1 DO1& E1 FVQ
• (R)-Streptonigrin
• 2-Pyridinecarboxylic acid,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-
• 5-Amino-6-(7-amino-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid
• 5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid
• Picolinic acid,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-
• Picolinic acid,8-dihydro-7-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-
• Nigrin (TN)
• Streptonigrin from Streptomyces flocculus
• Opera_ID_823
• 5278 R.P.
• STREPTONIGRIN [MI]
• NCIMech_000191
• SCHEMBL3940
• 5-25-17-00308 (Beilstein Handbook Reference)
• MLS004556149
• CHEMBL11417
• GTPL8683
• SCHEMBL1650605
• RUFOCROMOMYCIN [WHO-DD]
• SCHEMBL17111078
• BDBM34650
• cid_5323583
• DTXSID00960034
• PVYJZLYGTZKPJE-UHFFFAOYSA-N
• HMS2230J24
• NSC56748
• BDBM50447758
• CCG-35398
• CCG-36481
• AKOS040742654
• SMP2_000320
• NCGC00247058-01
• (4E)-5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylic acid
• (4Z)-5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylic acid
• NCI60_004051
• NCI60_041843
• SMR003365494
• 2-Hydroxy-3,4-dimethoxyphenyl)-3-methyl-
• HY-124586
• CS-0087029
• C02081
• D05931
• Streptonigrin from Streptomyces flocculus, >=98%
• ANTIBIOTIC PRODUCED BY STREPTOMYCES FLOCCULUS
• SR-01000721857-3
• SR-01000721857-5
• Q15427845
• (4E)-5-amino-6-(7-amino-5,8-diketo-6-methoxy-2-quinolyl)-4-(6-keto-4,5-dimethoxy-cyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylic acid
• (4E)-5-amino-6-(7-amino-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(4,5-dimethoxy-6-oxo-1-cyclohexa-2,4-dienylidene)-3-methyl-1H-pyridine-2-carboxylic acid
• (4E)-5-Amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(4,5-dimethoxy-6-oxo-1-cyclohexa-2,4-dienylidene)-3-methyl-1H-pyridine-2-carboxylic acid
• (4E)-5-azanyl-6-[7-azanyl-6-methoxy-5,8-bis(oxidanylidene)quinolin-2-yl]-4-(4,5-dimethoxy-6-oxidanylidene-cyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylic acid
• 2-Pyridinecarboxylic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-, (4R)-
• 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxy-phenyl)-3-methyl-pyridine-2-carboxylic acid
• 5-Amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydro-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-2-pyridinecarboxylic acid #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9483	94.83%
Caco-2	-	0.7544	75.44%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5327	53.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9084	90.84%
OATP1B3 inhibitior	+	0.9271	92.71%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7630	76.30%
P-glycoprotein inhibitior	+	0.6141	61.41%
P-glycoprotein substrate	-	0.5623	56.23%
CYP3A4 substrate	+	0.5977	59.77%
CYP2C9 substrate	-	0.7932	79.32%
CYP2D6 substrate	-	0.8722	87.22%
CYP3A4 inhibition	-	0.7981	79.81%
CYP2C9 inhibition	-	0.5952	59.52%
CYP2C19 inhibition	-	0.5365	53.65%
CYP2D6 inhibition	-	0.8442	84.42%
CYP1A2 inhibition	-	0.6936	69.36%
CYP2C8 inhibition	+	0.7489	74.89%
CYP inhibitory promiscuity	+	0.5640	56.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Danger	0.4639	46.39%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9312	93.12%
Skin irritation	-	0.8321	83.21%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5224	52.24%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.6177	61.77%
skin sensitisation	-	0.9086	90.86%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6356	63.56%
Acute Oral Toxicity (c)	III	0.5844	58.44%
Estrogen receptor binding	+	0.8344	83.44%
Androgen receptor binding	+	0.6942	69.42%
Thyroid receptor binding	+	0.6316	63.16%
Glucocorticoid receptor binding	+	0.7476	74.76%
Aromatase binding	+	0.6963	69.63%
PPAR gamma	+	0.7150	71.50%
Honey bee toxicity	-	0.7937	79.37%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8547	85.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293277	O15118	Niemann-Pick C1 protein	562.3 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	125.9 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	446.7 nM	Potency	via Super-PRED
CHEMBL3797	Q13315	Serine-protein kinase ATM	707.9 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	316.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.05%	95.56%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	94.65%	94.42%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.50%	99.23%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	92.12%	96.67%
CHEMBL2581	P07339	Cathepsin D	91.31%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.13%	94.00%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	87.74%	95.48%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.70%	86.33%
CHEMBL1255126	O15151	Protein Mdm4	87.65%	90.20%
CHEMBL1951	P21397	Monoamine oxidase A	87.08%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.55%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.23%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.03%	93.56%
CHEMBL2535	P11166	Glucose transporter	84.20%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.02%	99.17%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	83.54%	95.72%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.99%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.39%	91.11%
CHEMBL301	P24941	Cyclin-dependent kinase 2	80.24%	91.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5298
• LOTUS: LTS0003499
• wikiData: Q15427845