5,21-Dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione

Details

• Internal ID: 68209182-08f8-4344-9bd0-c50d9b5dae3c
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Carbazoles > Pyrrolocarbazoles > Indolocarbazoles
• IUPAC Name: 5,21-dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
• SMILES (Canonical): COC1C(OC(C(C1O)O)N2C3=C(C=CC=C3Cl)C4=C5C(=C6C7=C(C(=CC=C7)Cl)NC6=C42)C(=O)NC5=O)CO
• SMILES (Isomeric): COC1C(OC(C(C1O)O)N2C3=C(C=CC=C3Cl)C4=C5C(=C6C7=C(C(=CC=C7)Cl)NC6=C42)C(=O)NC5=O)CO
• InChI: InChI=1S/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)
• InChI Key: QEHOIJJIZXRMAN-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₁Cl₂N₃O₇
• Molecular Weight: 570.40 g/mol
• Exact Mass: 569.0756554 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.25
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 5,21-Dichloro-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
• NSC359079
• NSC-359079
• Neuro_000196
• CHEMBL27000
• SCHEMBL12961242
• ICX5609244
• NCI60_003256
• SMR001565446
• A20190
• UNII-Y96MQM21V9; CHEMBL370100; Y96MQM21V9
• 5H-Indolo[2,4-c]carbasole-5,7(6H)-dione, 1,11-dichloro-12,13-dihydro-12-(4-O-methyl-.beta.-D-glucopyranosyl)-
• 5H-Indolo[2,4-c]carbazole-5,7(6H)-dione, 1,11-dichloro-12,13-dihydro-12-(4-O-methyl-.beta.-D-glucopyranosyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6598	65.98%
Caco-2	-	0.8655	86.55%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.3400	34.00%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.8605	86.05%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9757	97.57%
P-glycoprotein inhibitior	+	0.5964	59.64%
P-glycoprotein substrate	-	0.6710	67.10%
CYP3A4 substrate	+	0.7024	70.24%
CYP2C9 substrate	-	0.7970	79.70%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.7479	74.79%
CYP2C9 inhibition	-	0.6745	67.45%
CYP2C19 inhibition	-	0.7779	77.79%
CYP2D6 inhibition	-	0.8637	86.37%
CYP1A2 inhibition	-	0.8357	83.57%
CYP2C8 inhibition	+	0.5548	55.48%
CYP inhibitory promiscuity	-	0.6600	66.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7538	75.38%
Carcinogenicity (trinary)	Non-required	0.4783	47.83%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9581	95.81%
Skin irritation	-	0.8071	80.71%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	+	0.5143	51.43%
skin sensitisation	-	0.8870	88.70%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8033	80.33%
Acute Oral Toxicity (c)	III	0.6511	65.11%
Estrogen receptor binding	+	0.7333	73.33%
Androgen receptor binding	+	0.6208	62.08%
Thyroid receptor binding	+	0.5451	54.51%
Glucocorticoid receptor binding	+	0.7246	72.46%
Aromatase binding	+	0.6257	62.57%
PPAR gamma	+	0.7685	76.85%
Honey bee toxicity	-	0.8222	82.22%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6047	60.47%
Fish aquatic toxicity	-	0.4049	40.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.91%	94.45%
CHEMBL2581	P07339	Cathepsin D	98.38%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.17%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	96.64%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.56%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.15%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.01%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	93.76%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.56%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.63%	97.09%
CHEMBL1781	P11387	DNA topoisomerase I	88.35%	97.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.13%	97.25%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	87.63%	95.71%
CHEMBL3384	Q16512	Protein kinase N1	86.86%	80.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.68%	89.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.01%	90.08%
CHEMBL230	P35354	Cyclooxygenase-2	85.29%	89.63%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.68%	93.99%
CHEMBL220	P22303	Acetylcholinesterase	83.15%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.15%	93.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.75%	97.14%
CHEMBL5957	P21589	5'-nucleotidase	82.71%	97.78%
CHEMBL5314	Q06418	Tyrosine-protein kinase receptor TYRO3	82.34%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.59%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.38%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.11%	92.62%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.40%	85.94%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.36%	96.00%

Plants that contains it

• Schizanthus grahamii

Cross-Links

• PubChem: 5043
• LOTUS: LTS0154938
• wikiData: Q104966553