beta-Rubromycin

Details

• Internal ID: 29333ee5-edfd-4f34-b89b-bf160cc06c82
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Pyranochromenes
• IUPAC Name: methyl (2S)-8',10-dihydroxy-5',7'-dimethoxy-4',9,9'-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
• SMILES (Canonical): COC1=CC(=C(C2=C1C(=O)C3=C(C2=O)OC4(C3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O)OC
• SMILES (Isomeric): COC1=CC(=C(C2=C1C(=O)C3=C(C2=O)O[C@]4(C3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O)OC
• InChI: InChI=1S/C27H20O12/c1-34-13-8-14(35-2)20(29)18-17(13)19(28)12-9-27(39-24(12)22(18)31)5-4-10-6-11-7-15(25(32)36-3)37-26(33)16(11)21(30)23(10)38-27/h6-8,29-30H,4-5,9H2,1-3H3/t27-/m0/s1
• InChI Key: FXCBZGHGMRSWJD-MHZLTWQESA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₀O₁₂
• Molecular Weight: 536.40 g/mol
• Exact Mass: 536.09547607 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 27267-70-5
• CHEMBL2170857
• methyl (2S)-8',10-dihydroxy-5',7'-dimethoxy-4',9,9'-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
• ??-Rubromycin
• DTXSID30181715
• BDBM50396098
• HB3798
• AKOS040754624
• HY-122482
• CS-0085691
• methyl (2S)-8',10-dihydroxy-5',7'-dimethoxy-4',9,9'-trioxo-spiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f]benzofuran]-7-carboxylate
• Methyl-8,10'-dihydroxy-5,7-dimethoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spirofuran-2,2'-pyranochromene]-7'-carboxylate
• Spiro(benzo(1,2-b:5,4-c')dipyran-2(3H),2'(3'H)-naphtho(1,2-b)furan)-7-carboxylic acid, 4,4',5',9-tetrahydro-6',10-dihydroxy-7',9'-dimethoxy-4',5',9-trioxo-, methyl ester
• Spiro[benzo[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphtho[2,3-b]furan]-7-carboxylic acid, 4,4',9,9'-tetrahydro-8',10-dihydroxy-5',7'-dimethoxy-4',9,9'-trioxo-, methyl ester, (2S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9130	91.30%
Caco-2	-	0.7613	76.13%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8585	85.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8299	82.99%
OATP1B3 inhibitior	+	0.9349	93.49%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9432	94.32%
P-glycoprotein inhibitior	+	0.7459	74.59%
P-glycoprotein substrate	+	0.5447	54.47%
CYP3A4 substrate	+	0.6740	67.40%
CYP2C9 substrate	+	0.6272	62.72%
CYP2D6 substrate	-	0.8565	85.65%
CYP3A4 inhibition	-	0.6126	61.26%
CYP2C9 inhibition	-	0.7026	70.26%
CYP2C19 inhibition	-	0.6307	63.07%
CYP2D6 inhibition	-	0.8153	81.53%
CYP1A2 inhibition	+	0.5155	51.55%
CYP2C8 inhibition	+	0.6290	62.90%
CYP inhibitory promiscuity	-	0.5587	55.87%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.6827	68.27%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8732	87.32%
Skin irritation	-	0.7355	73.55%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4447	44.47%
Micronuclear	+	0.5559	55.59%
Hepatotoxicity	-	0.5174	51.74%
skin sensitisation	-	0.8261	82.61%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8431	84.31%
Acute Oral Toxicity (c)	I	0.4997	49.97%
Estrogen receptor binding	+	0.8459	84.59%
Androgen receptor binding	+	0.7451	74.51%
Thyroid receptor binding	+	0.5184	51.84%
Glucocorticoid receptor binding	+	0.9106	91.06%
Aromatase binding	+	0.7482	74.82%
PPAR gamma	+	0.7231	72.31%
Honey bee toxicity	-	0.7922	79.22%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9830	98.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.45%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.96%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.90%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.62%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.34%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.81%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.43%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.57%	86.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.68%	96.38%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.08%	93.99%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.13%	94.42%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.86%	96.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.79%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.59%	90.00%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	84.19%	80.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.05%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.71%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.40%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.91%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	82.81%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.07%	91.07%
CHEMBL2535	P11166	Glucose transporter	81.74%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.55%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.09%	99.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5464074
• LOTUS: LTS0120145
• wikiData: Q72506855