Epsilon-pyrromycinone

Details

• Internal ID: f7c10281-97f7-4e76-81f5-379251a7d120
• Taxonomy: Benzenoids > Naphthacenes > Tetracenequinones
• IUPAC Name: methyl (1R,2R,4S)-2-ethyl-2,4,5,7,10-pentahydroxy-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(C=CC(=C4C3=O)O)O)O)O)O
• SMILES (Isomeric): CC[C@]1(C[C@@H](C2=C(C3=C(C=C2[C@H]1C(=O)OC)C(=O)C4=C(C=CC(=C4C3=O)O)O)O)O)O
• InChI: InChI=1S/C22H20O9/c1-3-22(30)7-12(25)13-8(17(22)21(29)31-2)6-9-14(19(13)27)20(28)16-11(24)5-4-10(23)15(16)18(9)26/h4-6,12,17,23-25,27,30H,3,7H2,1-2H3/t12-,17-,22+/m0/s1
• InChI Key: RWCVSDKDFSVZNF-KRYGIPSASA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₉
• Molecular Weight: 428.40 g/mol
• Exact Mass: 428.11073221 g/mol
• Topological Polar Surface Area (TPSA): 162.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• Epsilon-pyrromycinone
• Eta-Pyrromycinon
• Rutilantinon
• Antibiotic MA 144D2
• PYRROMYCINONE, EPSILON
• 1-hydroxyaklavinone
• Galirubine
• MA 144D2
• epsilon-pyrromy-cinone
• NSC 114778
• Spectrum_000795
• Spectrum2_000452
• Spectrum3_001155
• Spectrum4_001432
• Spectrum5_000284
• BSPBio_002709
• KBioGR_001904
• KBioSS_001275
• SPECTRUM201606
• SPBio_000524
• CHEMBL3039086
• KBio2_001275
• KBio2_003843
• KBio2_006411
• KBio3_002209
• CHEBI:108590
• RWCVSDKDFSVZNF-KRYGIPSASA-N
• HMS1923A07
• CCG-38694
• SDCCGMLS-0066382.P001
• NCGC00178516-01
• 1-Naphthacenecarboxylic acid, 1,2,3,4,6,11-hexahydro-2-ethyl-2,4,5,7,10-pentahydroxy-6,11-dioxo-, methyl ester, (1R,2R,4S)-
• 1-Naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7,10-pentahydroxy-6,11-dioxo-, methyl ester, (1R,2R,4S)-
• SR-05000002666
• SR-05000002666-1
• BRD-K11258719-001-03-2
• Q27187513
• (1R,2R,4S)-2-ethyl-2,4,5,7,10-pentahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylic acid methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9797	97.97%
Caco-2	-	0.7404	74.04%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6924	69.24%
OATP2B1 inhibitior	+	0.7133	71.33%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7424	74.24%
P-glycoprotein inhibitior	-	0.7581	75.81%
P-glycoprotein substrate	+	0.5546	55.46%
CYP3A4 substrate	+	0.6251	62.51%
CYP2C9 substrate	-	0.5942	59.42%
CYP2D6 substrate	-	0.8628	86.28%
CYP3A4 inhibition	-	0.6517	65.17%
CYP2C9 inhibition	-	0.8399	83.99%
CYP2C19 inhibition	-	0.8722	87.22%
CYP2D6 inhibition	-	0.8188	81.88%
CYP1A2 inhibition	-	0.7484	74.84%
CYP2C8 inhibition	-	0.6133	61.33%
CYP inhibitory promiscuity	-	0.7475	74.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8743	87.43%
Carcinogenicity (trinary)	Non-required	0.6583	65.83%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.8126	81.26%
Skin irritation	-	0.7315	73.15%
Skin corrosion	-	0.9183	91.83%
Ames mutagenesis	+	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5579	55.79%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	-	0.5196	51.96%
skin sensitisation	-	0.9099	90.99%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5643	56.43%
Estrogen receptor binding	+	0.8760	87.60%
Androgen receptor binding	+	0.7149	71.49%
Thyroid receptor binding	-	0.5474	54.74%
Glucocorticoid receptor binding	+	0.8716	87.16%
Aromatase binding	+	0.6451	64.51%
PPAR gamma	+	0.8168	81.68%
Honey bee toxicity	-	0.8676	86.76%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9864	98.64%

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	99.47%	91.11%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	98.90%	96.38%
CHEMBL2581	P07339	Cathepsin D	97.18%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.36%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.91%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.25%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.62%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.24%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.65%	90.71%
CHEMBL4208	P20618	Proteasome component C5	86.31%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.91%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	82.47%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.10%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 159908
• LOTUS: LTS0145577
• wikiData: Q27187513