Coumermycin A1

Details

• Internal ID: 0ac17234-5a0d-485f-99b0-5f73e25d2ed6
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[5-[[4-hydroxy-7-[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]carbamoyl]-4-methyl-1H-pyrrole-3-carbonyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
• InChI: InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1
• InChI Key: WTIJXIZOODAMJT-DHFGXMAYSA-N
• Popularity: 611 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₅₉N₅O₂₀
• Molecular Weight: 1110.10 g/mol
• Exact Mass: 1109.37533929 g/mol
• Topological Polar Surface Area (TPSA): 347.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 5.57
• H-Bond Acceptor: 20
• H-Bond Donor: 9
• Rotatable Bonds: 14

Synonyms

• COUMERMYCIN
• 4434-05-3
• Coumamycine
• Coumamycinum
• Cumamicina
• Coumamycin
• Sugordomycin D-1a
• Notomycin A1
• Notomycin
• PCH9QZ1IIH
• NSC 107412
• CHEBI:3907
• DTXSID901023379
• [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[5-[[4-hydroxy-7-[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]carbamoyl]-4-methyl-1H-pyrrole-3-carbonyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
• NSC-107412
• ((3R,4S,5R,6R)-5-hydroxy-6-(4-hydroxy-3-((5-((4-hydroxy-7-((2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl)oxy-8-methyl-2-oxochromen-3-yl)carbamoyl)-4-methyl-1H-pyrrole-3-carbonyl)amino)-8-methyl-2-oxochromen-7-yl)oxy-3-methoxy-2,2-dimethyloxan-4-yl) 5-methyl-1H-pyrrole-2-carboxylate
• RefChem:128252
• DTXCID301507719
• ((3R,4S,5R)-5-Hydroxy-6-(2-hydroxy-3-((4-((2-hydroxy-7-((3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl)oxy-8-methyl-4-oxochromen-3-yl)carbamoyl)-3-methyl-1H-pyrrole-2-carbonyl)amino)-8-methyl-4-oxochromen-7-yl)oxy-3-methoxy-2,2-dimethyloxan-4-yl) 5-methyl-1H-pyrrole-2-carboxylate
• ((3R,4S,5R)-5-hydroxy-6-(2-hydroxy-3-((5-((2-hydroxy-7-((3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl)oxy-8-methyl-4-oxochromen-3-yl)carbamoyl)-4-methyl-1H-pyrrole-3-carbonyl)amino)-8-methyl-4-oxochromen-7-yl)oxy-3-methoxy-2,2-dimethyloxan-4-yl) 5-methyl-1H-pyrrole-2-carboxylate
• 2-N,4-N-bis(4-hydroxy-7-((2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl)oxy-8-methyl-2-oxochromen-3-yl)-3-methyl-1H-pyrrole-2,4-dicarboximidic acid
• ((3R,4S,5R,6R)-5-hydroxy-6-(4-hydroxy-3-((5-((4-hydroxy-7-((2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxy-tetrahydropyran-2-yl)oxy-8-methyl-2-oxo-chromen-3-yl)carbamoyl)-4-methyl-1H-pyrrole-3-carbonyl)amino)-8-methyl-2-oxo-chromen-7-yl)oxy-3-methoxy-2,2-dimethyl-tetrahydropyran-4-yl) 5-methyl-1H-pyrrole-2-carboxylate
• Coumamycin [INN]
• Coumermycin (USAN)
• Coumermycin [USAN]
• CHEMBL4555272
• C05073
• D02333
• Sugordomycin D-la
• Cumamycinum
• BHW
• Coumamycin (VAN)
• UNII-PCH9QZ1IIH
• Coumamycine [INN-French]
• Coumamycinum [INN-Latin]
• Cumamicina [INN-Spanish]
• SCHEMBL194268
• orb1694032
• SCHEMBL29420686
• EX-A7846E
• GTPL10879
• HY-N7452
• BDBM50613606
• AKOS040755049
• BRN 0470805
• CS-0129352
• NS00011812
• (3-methyl-1H-pyrrole-2,4-diyl)bis[carbonylimino(4-hydroxy-8-methyl-2-oxo-2H-chromene-3,7-diyl)oxy(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2,4-diyl] bis(5-methyl-1H-pyrrole-2-carboxylate)
• 1H-PYRROLE-2,4-DICARBOXAMIDE, N2,N4-BIS(7-((6-DEOXY-5-C-METHYL-4-O-METHYL-3-O-((5-METHYL-1H-PYRROL-2-YL)CARBONYL)-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-4-HYDROXY-8-METHYL-2-OXO-2H-1-BENZOPYRAN-3-YL)-3-METHYL-
• 1H-Pyrrole-2-carboxylic acid, 5-methyl-, diester with N,N'-bis(7-((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-3-methyl-1H-pyrrole-2,4-dicarboxamide
• 5-Methylpyrrole-2-carboxylic acid, diester with 3,3'-((3-methylpyrrole-2,4-diyl)bis(carbonylimino))bis(4-hydroxy-8-methyl-7-((tetrahydro-3,4-dihydroxy-5-methoxy-6,6-dimethylpyran-2-yl)oxy)coumarin)
• 5-METHYLPYYROLE-2-CARBOXYLIC ACID, DIESTER WITH 3,3'-((3-METHYLPYRROLE-2,4-DIYL)BIS(CARBONYLIMINO))BIS(4-HYDROXY-8-METHYL-7-((TETRAHYDRO-3,4-DIHYDROXY-5-METHOXY-6,6-DIMETHYLPYRAN-2-YL)OXY)COUMARIN)
• Pyrrole-2-carboxylic acid, 5-methyl-, diester with 3,3'-((3-methylpyrrole-2,4-diyl)bis(carbonylimino))bis(7-((5,5-di-C-methyl-4-O-methyl-alpha-L-lyxopyranosyl)oxy)-4-hydroxy-8-methylcoumarin)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4753	47.53%
Caco-2	-	0.8558	85.58%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4247	42.47%
OATP2B1 inhibitior	-	0.5774	57.74%
OATP1B1 inhibitior	+	0.8503	85.03%
OATP1B3 inhibitior	+	0.9354	93.54%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9817	98.17%
P-glycoprotein inhibitior	+	0.7463	74.63%
P-glycoprotein substrate	+	0.7402	74.02%
CYP3A4 substrate	+	0.7303	73.03%
CYP2C9 substrate	+	0.5738	57.38%
CYP2D6 substrate	-	0.8697	86.97%
CYP3A4 inhibition	-	0.6627	66.27%
CYP2C9 inhibition	-	0.7104	71.04%
CYP2C19 inhibition	-	0.8230	82.30%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.6099	60.99%
CYP2C8 inhibition	+	0.7672	76.72%
CYP inhibitory promiscuity	-	0.5165	51.65%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5248	52.48%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8971	89.71%
Skin irritation	-	0.8204	82.04%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.5978	59.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6916	69.16%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5469	54.69%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8406	84.06%
Acute Oral Toxicity (c)	III	0.6984	69.84%
Estrogen receptor binding	+	0.6894	68.94%
Androgen receptor binding	+	0.7714	77.14%
Thyroid receptor binding	+	0.6560	65.60%
Glucocorticoid receptor binding	+	0.7421	74.21%
Aromatase binding	+	0.7195	71.95%
PPAR gamma	+	0.7648	76.48%
Honey bee toxicity	-	0.7053	70.53%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8350	83.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.11%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.01%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	97.68%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	96.22%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.92%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.29%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.26%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.21%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.01%	91.07%
CHEMBL2535	P11166	Glucose transporter	88.68%	98.75%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.27%	97.28%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.70%	83.57%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	87.17%	85.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.98%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.42%	83.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.18%	94.42%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.71%	94.33%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	83.63%	96.47%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.58%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.32%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.30%	92.88%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.26%	81.11%
CHEMBL340	P08684	Cytochrome P450 3A4	83.24%	91.19%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.02%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	82.65%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	82.49%	94.75%
CHEMBL1871	P10275	Androgen Receptor	80.30%	96.43%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54675768
• LOTUS: LTS0239572
• wikiData: Q15408415