Aclucinomycin A

Details

• Internal ID: 8dd9e7b2-a69f-4be3-8c16-425b3a7d8967
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: methyl (1R,2R,4S)-4-[4-(dimethylamino)-5-[4-hydroxy-6-methyl-5-(6-methyl-5-oxooxan-2-yl)oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• SMILES (Canonical): CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O
• SMILES (Isomeric): CC[C@]1(C[C@@H](C2=C(C3=C(C=C2[C@H]1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O
• InChI: InChI=1S/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3/t18?,19?,20?,24?,27?,28-,29?,30?,31?,35-,39?,40?,42+/m0/s1
• InChI Key: USZYSDMBJDPRIF-XCKHQVGJSA-N
• Popularity: 716 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₅₃NO₁₅
• Molecular Weight: 811.90 g/mol
• Exact Mass: 811.34151998 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.16
• H-Bond Acceptor: 16
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

• 79617-46-2
• NSC208734
• NSC 208734
• methyl (1R,2R,4S)-4-[4-(dimethylamino)-5-[4-hydroxy-6-methyl-5-(6-methyl-5-oxooxan-2-yl)oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• Antibiotic MA144-A1
• 57576-44-0
• CHEMBL45414
• DivK1c_000678
• SCHEMBL1649619
• HMS502B20
• KBio1_000678
• NINDS_000678
• NSC240619
• NSC-240619
• IDI1_000678
• QTL1_000003
• NCI60_001746
• PD011255
• 1-Naphthacenecarboxylic acid,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-[[2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-((2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-.alpha.-L-lyxo-hexopyranosyl]-3-(dimethylamino)-.alpha.-L-lyxo-hexopyranosyl]oxy]-, methyl ester, radical ion(1-), (1R-(1.alpha.,2.beta.,4.beta.))-
• 1-Naphthacenecarboxylic acid,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-[[2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-((2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-.alpha.-L-lyxo-hexopyranosyl]-3-(dimethylamino)-.alpha.-L-lyxo-hexopyranosyl]oxy]-, methyl ester,(1R-(1.alpha.,2.beta.,4.beta.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7345	73.45%
Caco-2	-	0.8663	86.63%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4897	48.97%
OATP2B1 inhibitior	-	0.7166	71.66%
OATP1B1 inhibitior	+	0.8864	88.64%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	+	0.8892	88.92%
P-glycoprotein inhibitior	+	0.7603	76.03%
P-glycoprotein substrate	+	0.8572	85.72%
CYP3A4 substrate	+	0.7424	74.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8450	84.50%
CYP3A4 inhibition	-	0.7552	75.52%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8278	82.78%
CYP2D6 inhibition	-	0.8179	81.79%
CYP1A2 inhibition	-	0.6122	61.22%
CYP2C8 inhibition	+	0.5515	55.15%
CYP inhibitory promiscuity	-	0.8501	85.01%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5909	59.09%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9104	91.04%
Skin irritation	-	0.8019	80.19%
Skin corrosion	-	0.9367	93.67%
Ames mutagenesis	+	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4491	44.91%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.8903	89.03%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7977	79.77%
Acute Oral Toxicity (c)	II	0.7313	73.13%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5383	53.83%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.8087	80.87%
Honey bee toxicity	-	0.7075	70.75%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8733	87.33%

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	99.76%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.31%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.88%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	96.86%	96.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.24%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.33%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.99%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	93.68%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.18%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.19%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.42%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.91%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.92%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.85%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.18%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.85%	86.33%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.76%	83.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	85.59%	96.00%
CHEMBL4208	P20618	Proteasome component C5	85.17%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.66%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.54%	90.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.08%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.51%	99.17%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.07%	96.67%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.45%	95.83%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.71%	97.33%
CHEMBL3401	O75469	Pregnane X receptor	81.59%	94.73%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.66%	85.11%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.10%	91.07%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 308141
• LOTUS: LTS0250346
• wikiData: Q105278628