Isoquinocycline A

Details

• Internal ID: ef0c90ac-7051-4bac-a0b5-0c6197b8b970
• Taxonomy: Benzenoids > Naphthacenes > Tetracenequinones
• IUPAC Name: (16R,17R,19R)-16-[4,5-dihydroxy-5-(1-hydroxyethyl)-6-methyloxan-2-yl]oxy-3,10-dihydroxy-17-methylspiro[18-oxapentacyclo[15.2.1.02,15.04,13.06,11]icosa-2,4(13),6(11),7,9,14-hexaene-19,5'-3,6-dihydro-2H-pyrrolo[2,3-b]pyrrole]-5,12-dione
• SMILES (Canonical): CC1C(C(CC(O1)OC2C3=CC4=C(C(=C3C5CC2(OC56C=C7CCN=C7N6)C)O)C(=O)C8=C(C4=O)C(=CC=C8)O)O)(C(C)O)O
• SMILES (Isomeric): CC1C(C(CC(O1)O[C@@H]2C3=CC4=C(C(=C3C5C[C@]2(O[C@]56C=C7CCN=C7N6)C)O)C(=O)C8=C(C4=O)C(=CC=C8)O)O)(C(C)O)O
• InChI: InChI=1S/C33H34N2O10/c1-13(36)33(42)14(2)43-22(10-21(33)38)44-29-18-9-17-25(26(39)16-5-4-6-20(37)24(16)27(17)40)28(41)23(18)19-12-31(29,3)45-32(19)11-15-7-8-34-30(15)35-32/h4-6,9,11,13-14,19,21-22,29,36-38,41-42H,7-8,10,12H2,1-3H3,(H,34,35)/t13?,14?,19?,21?,22?,29-,31-,32-,33?/m1/s1
• InChI Key: LHDJGLQULHMCSJ-WGNOBJAYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₄N₂O₁₀
• Molecular Weight: 618.60 g/mol
• Exact Mass: 618.22134529 g/mol
• Topological Polar Surface Area (TPSA): 187.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.84
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8524	85.24%
Caco-2	-	0.8674	86.74%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5610	56.10%
OATP2B1 inhibitior	-	0.5808	58.08%
OATP1B1 inhibitior	+	0.8496	84.96%
OATP1B3 inhibitior	+	0.9287	92.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9533	95.33%
P-glycoprotein inhibitior	+	0.6906	69.06%
P-glycoprotein substrate	+	0.8012	80.12%
CYP3A4 substrate	+	0.7486	74.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	-	0.9444	94.44%
CYP2C9 inhibition	-	0.7342	73.42%
CYP2C19 inhibition	-	0.7048	70.48%
CYP2D6 inhibition	-	0.8941	89.41%
CYP1A2 inhibition	-	0.8202	82.02%
CYP2C8 inhibition	+	0.6475	64.75%
CYP inhibitory promiscuity	-	0.8431	84.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4969	49.69%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.9299	92.99%
Skin irritation	-	0.7550	75.50%
Skin corrosion	-	0.9205	92.05%
Ames mutagenesis	+	0.7130	71.30%
Human Ether-a-go-go-Related Gene inhibition	+	0.6943	69.43%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8235	82.35%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7545	75.45%
Acute Oral Toxicity (c)	III	0.5438	54.38%
Estrogen receptor binding	+	0.8724	87.24%
Androgen receptor binding	+	0.7727	77.27%
Thyroid receptor binding	+	0.5989	59.89%
Glucocorticoid receptor binding	+	0.7648	76.48%
Aromatase binding	+	0.7640	76.40%
PPAR gamma	+	0.7526	75.26%
Honey bee toxicity	-	0.6858	68.58%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9099	90.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	99.87%	96.38%
CHEMBL2581	P07339	Cathepsin D	99.47%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.44%	91.11%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	99.03%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.57%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.29%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	97.28%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.28%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	96.49%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.87%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.64%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.16%	99.15%
CHEMBL1937	Q92769	Histone deacetylase 2	92.61%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.83%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	91.41%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.32%	86.33%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.09%	92.88%
CHEMBL284	P27487	Dipeptidyl peptidase IV	89.39%	95.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.18%	97.25%
CHEMBL2094135	Q96BI3	Gamma-secretase	89.05%	98.05%
CHEMBL1951	P21397	Monoamine oxidase A	88.89%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.58%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.45%	94.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.35%	83.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.21%	95.93%
CHEMBL1914	P06276	Butyrylcholinesterase	87.71%	95.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.44%	93.56%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	87.26%	85.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.22%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.19%	93.40%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.49%	97.14%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.55%	96.67%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	83.09%	95.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.90%	93.03%
CHEMBL2535	P11166	Glucose transporter	81.45%	98.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.37%	82.69%
CHEMBL4444	P04070	Vitamin K-dependent protein C	81.29%	93.89%
CHEMBL290	Q13370	Phosphodiesterase 3B	81.13%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.71%	90.08%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139584523
• LOTUS: LTS0023022
• wikiData: Q104955883