7,19-Difluoro-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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: 004ada71-cf88-468d-a8fd-4a54ab13ab20
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Carbazoles > Pyrrolocarbazoles > Indolocarbazoles
• IUPAC Name: 7,19-difluoro-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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): C1=CC2=C(C=C1F)C3=C4C(=C5C6=C(C=CC(=C6)F)N(C5=C3N2)C7C(C(C(C(O7)CO)O)O)O)C(=O)NC4=O
• SMILES (Isomeric): C1=CC2=C(C=C1F)C3=C4C(=C5C6=C(C=CC(=C6)F)N(C5=C3N2)C7C(C(C(C(O7)CO)O)O)O)C(=O)NC4=O
• InChI: InChI=1S/C26H19F2N3O7/c27-8-1-3-12-10(5-8)15-17-18(25(37)30-24(17)36)16-11-6-9(28)2-4-13(11)31(20(16)19(15)29-12)26-23(35)22(34)21(33)14(7-32)38-26/h1-6,14,21-23,26,29,32-35H,7H2,(H,30,36,37)
• InChI Key: YQUUXCMYRDQFPL-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₁₉F₂N₃O₇
• Molecular Weight: 523.40 g/mol
• Exact Mass: 523.11910628 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.56
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• BDBM50142927
• 12-(3,4-dihydroxy-6-hydroxymethyl-5-methoxytetrahydro-2H-2-pyranyl)-3,9-difluoro-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
• 3,9-difluoro-12-(3,4,5-trihydroxy-6-hydroxymethyltetrahydro-2H-2-pyranyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6583	65.83%
Caco-2	-	0.8604	86.04%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.5315	53.15%
OATP2B1 inhibitior	-	0.5640	56.40%
OATP1B1 inhibitior	+	0.8460	84.60%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9316	93.16%
BSEP inhibitior	+	0.9139	91.39%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.6907	69.07%
CYP3A4 substrate	+	0.6073	60.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8514	85.14%
CYP3A4 inhibition	-	0.9461	94.61%
CYP2C9 inhibition	-	0.8911	89.11%
CYP2C19 inhibition	-	0.9078	90.78%
CYP2D6 inhibition	-	0.8784	87.84%
CYP1A2 inhibition	-	0.7424	74.24%
CYP2C8 inhibition	+	0.4544	45.44%
CYP inhibitory promiscuity	-	0.8132	81.32%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7938	79.38%
Carcinogenicity (trinary)	Non-required	0.5418	54.18%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9532	95.32%
Skin irritation	-	0.7872	78.72%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	+	0.5336	53.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6467	64.67%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	-	0.5233	52.33%
skin sensitisation	-	0.8757	87.57%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8803	88.03%
Nephrotoxicity	-	0.8564	85.64%
Acute Oral Toxicity (c)	III	0.5543	55.43%
Estrogen receptor binding	+	0.6958	69.58%
Androgen receptor binding	+	0.6567	65.67%
Thyroid receptor binding	+	0.5162	51.62%
Glucocorticoid receptor binding	+	0.5725	57.25%
Aromatase binding	+	0.5832	58.32%
PPAR gamma	+	0.7810	78.10%
Honey bee toxicity	-	0.8445	84.45%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.3642	36.42%

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	98.78%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.25%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.52%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	95.90%	86.92%
CHEMBL2581	P07339	Cathepsin D	95.83%	98.95%
CHEMBL1781	P11387	DNA topoisomerase I	93.98%	97.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.76%	93.99%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.59%	96.61%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	92.56%	85.49%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	92.39%	87.16%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.33%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.08%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	91.96%	91.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	90.16%	93.04%
CHEMBL255	P29275	Adenosine A2b receptor	90.00%	98.59%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.78%	89.67%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	89.66%	93.24%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	89.10%	89.44%
CHEMBL213	P08588	Beta-1 adrenergic receptor	88.34%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.58%	95.89%
CHEMBL3384	Q16512	Protein kinase N1	87.02%	80.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.06%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.97%	89.62%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.35%	85.11%
CHEMBL1937	Q92769	Histone deacetylase 2	84.25%	94.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.26%	93.03%
CHEMBL4530	P00488	Coagulation factor XIII	83.14%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.78%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.35%	97.25%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	80.54%	99.09%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	80.42%	81.14%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 23442826
• LOTUS: LTS0259706
• wikiData: Q105352588