Clorobiocin

Details

• Internal ID: bf9ecba5-eb25-4d1b-a7d1-7bc1c1516d2c
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
• SMILES (Canonical): CC1=CC=C(N1)C(=O)OC2C(C(OC(C2OC)(C)C)OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CC(=C(C=C5)O)CC=C(C)C)O)Cl)O
• SMILES (Isomeric): CC1=CC=C(N1)C(=O)O[C@H]2[C@H]([C@@H](OC([C@@H]2OC)(C)C)OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CC(=C(C=C5)O)CC=C(C)C)O)Cl)O
• InChI: InChI=1S/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1
• InChI Key: FJAQNRBDVKIIKK-LFLQOBSNSA-N
• Popularity: 102 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₃₇ClN₂O₁₁
• Molecular Weight: 697.10 g/mol
• Exact Mass: 696.2085877 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.37
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• Chlorobiocin
• 39868-96-7
• Antibiotic RP 18,631
• RP 18631
• NSC 227186
• 18631 RP
• RP 18,631
• CHEMBL303984
• [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxo-chromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydropyran-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
• [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
• 18 631 R.P.
• 1kzn
• SCHEMBL315426
• SCHEMBL6937051
• GTPL12127
• DTXSID401028112
• BDBM50330317
• AKOS040746715
• DB03966
• 1H-Pyrrole-2-carboxylic acid, 5-methyl-, 3'-ester with N-(8-chloro-7-((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy)-4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-butenyl)benzamide
• HY-123515
• CS-0082871
• 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-({1-[4-hydroxy-3-(3-methyl-but-2-enyl)-phenyl]-methanoyl}-amino)-2-oxo-2H-1-benzopyran-7-yloxy]-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester
• 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6S)-6-{8-chloro-4-hydroxy-3-[4-hydroxy-3-(3-methyl-but-2-enyl)-benzoylamino]-2-oxo-2H-chromen-7-yloxy}-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester
• 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6S)-6-{8-chloro-4-hydroxy-3-[4-hydroxy-3-(4-methyl-pent-3-enyl)-benzoylamino]-2-oxo-2H-chromen-7-yloxy}-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester
• N-[8-chloro-7-({6-deoxy-5-methyl-4-O-methyl-3-O-[(5-methyl-1H-pyrrol-2-yl)carbonyl]-beta-D-gulopyranosyl}oxy)-4-hydroxy-2-oxo-2H-chromen-3-yl]-4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9536	95.36%
Caco-2	-	0.8671	86.71%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4294	42.94%
OATP2B1 inhibitior	+	0.6098	60.98%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9187	91.87%
MATE1 inhibitior	-	0.8472	84.72%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9662	96.62%
P-glycoprotein inhibitior	+	0.7685	76.85%
P-glycoprotein substrate	+	0.7603	76.03%
CYP3A4 substrate	+	0.7298	72.98%
CYP2C9 substrate	+	0.5914	59.14%
CYP2D6 substrate	-	0.8661	86.61%
CYP3A4 inhibition	-	0.8180	81.80%
CYP2C9 inhibition	-	0.5979	59.79%
CYP2C19 inhibition	-	0.6369	63.69%
CYP2D6 inhibition	-	0.8654	86.54%
CYP1A2 inhibition	-	0.7642	76.42%
CYP2C8 inhibition	+	0.8438	84.38%
CYP inhibitory promiscuity	+	0.6217	62.17%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7738	77.38%
Carcinogenicity (trinary)	Danger	0.5015	50.15%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9248	92.48%
Skin irritation	-	0.7821	78.21%
Skin corrosion	-	0.9309	93.09%
Ames mutagenesis	-	0.6178	61.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6854	68.54%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.8545	85.45%
skin sensitisation	-	0.8468	84.68%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7643	76.43%
Acute Oral Toxicity (c)	III	0.6528	65.28%
Estrogen receptor binding	+	0.8247	82.47%
Androgen receptor binding	+	0.8059	80.59%
Thyroid receptor binding	+	0.5636	56.36%
Glucocorticoid receptor binding	+	0.7301	73.01%
Aromatase binding	+	0.6933	69.33%
PPAR gamma	+	0.7559	75.59%
Honey bee toxicity	-	0.7032	70.32%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9909	99.09%

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	99.81%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	99.27%	89.34%
CHEMBL1951	P21397	Monoamine oxidase A	99.14%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.10%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	96.46%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	95.52%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.95%	94.00%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	93.65%	85.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.36%	95.89%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.22%	83.57%
CHEMBL340	P08684	Cytochrome P450 3A4	91.65%	91.19%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	90.76%	96.90%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.29%	95.56%
CHEMBL3194	P02766	Transthyretin	89.20%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.44%	86.33%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	88.28%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.95%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.61%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	87.53%	83.82%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	87.12%	94.42%
CHEMBL2535	P11166	Glucose transporter	86.42%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.59%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.46%	99.17%
CHEMBL4805	Q99572	P2X purinoceptor 7	85.15%	97.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.13%	97.28%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.74%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.73%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.86%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.40%	93.99%
CHEMBL2104	Q99571	P2X purinoceptor 4	82.28%	97.50%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.84%	85.49%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.79%	92.88%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.29%	83.00%
CHEMBL4530	P00488	Coagulation factor XIII	80.83%	96.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.12%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.10%	97.21%
CHEMBL2581	P07339	Cathepsin D	80.08%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.03%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54706138
• LOTUS: LTS0094711
• wikiData: Q104995959