Bastadin-21

Details

• Internal ID: 877ef469-b294-4c4f-9114-6308d86150a1
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (12E,25E)-16,21,32-tribromo-4,17-dihydroxy-12,25-bis(hydroxyimino)-2,19-dioxa-10,27-diazapentacyclo[28.2.2.220,23.13,7.114,18]octatriaconta-1(32),3,5,7(38),14(37),15,17,20,22,30,33,35-dodecaene-11,26-dione
• SMILES (Canonical): C1CNC(=O)C(=NO)CC2=CC(=C(C(=C2)Br)O)OC3=C(C=C(CC(=NO)C(=O)NCCC4=CC(=C(C=C4)OC5=C(C=CC1=C5)O)Br)C=C3)Br
• SMILES (Isomeric): C1CNC(=O)/C(=N/O)/CC2=CC(=C(C(=C2)Br)O)OC3=C(C=C(C/C(=N\O)/C(=O)NCCC4=CC(=C(C=C4)OC5=C(C=CC1=C5)O)Br)C=C3)Br
• InChI: InChI=1S/C34H29Br3N4O8/c35-22-11-18-2-5-28(22)48-30-16-19(1-4-27(30)42)8-10-39-34(45)26(41-47)15-21-13-24(37)32(43)31(17-21)49-29-6-3-20(12-23(29)36)14-25(40-46)33(44)38-9-7-18/h1-6,11-13,16-17,42-43,46-47H,7-10,14-15H2,(H,38,44)(H,39,45)/b40-25+,41-26+
• InChI Key: TUYUXKVFCXANLL-QHTJZBTGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₂₉Br₃N₄O₈
• Molecular Weight: 861.30 g/mol
• Exact Mass: 859.95150 g/mol
• Topological Polar Surface Area (TPSA): 182.00 Ų
• XlogP: 8.10
• Atomic LogP (AlogP): 6.75
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 0

Synonyms

• (12E,25E)-16,21,32-tribromo-4,17-dihydroxy-2,19-dioxa-10,27-diazapentacyclo[28.2.2.2~20,23~.1~3,7~.1~14,18~]octatriaconta-1(32),3(38),4,6,14(37),15,17,20,22,30,33,35-dodecaene-11,12,25,26-tetrone 12,2
• 2,19-dioxa-10,27-diazapentacyclo[28.2.2.2~20,23~.1~3,7~.1~14,18~]octatriaconta-3,5,7(38),14,16,18(37),20,22,30,32,33,35-dodecaene-11,12,25,26-tetrone, 16,21,32-tribromo-4,17-dihydroxy-, 12,25-dioxime,
• InChI=1/C34H29Br3N4O8/c35-22-11-18-2-5-28(22)48-30-16-19(1-4-27(30)42)8-10-39-34(45)26(41-47)15-21-13-24(37)32(43)31(17-21)49-29-6-3-20(12-23(29)36)14-25(40-46)33(44)38-9-7-18/h1-6,11-13,16-17,42-43,46-47H,7-10,14-15H2,(H,38,44)(H,39,45)/b40-25+,41-26

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8647	86.47%
Caco-2	-	0.8903	89.03%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Nucleus	0.5141	51.41%
OATP2B1 inhibitior	+	0.5690	56.90%
OATP1B1 inhibitior	+	0.9244	92.44%
OATP1B3 inhibitior	+	0.9326	93.26%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9880	98.80%
P-glycoprotein inhibitior	+	0.7853	78.53%
P-glycoprotein substrate	-	0.7709	77.09%
CYP3A4 substrate	+	0.5500	55.00%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.6977	69.77%
CYP2C9 inhibition	-	0.6282	62.82%
CYP2C19 inhibition	-	0.5817	58.17%
CYP2D6 inhibition	-	0.8431	84.31%
CYP1A2 inhibition	-	0.5608	56.08%
CYP2C8 inhibition	-	0.6045	60.45%
CYP inhibitory promiscuity	-	0.7236	72.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6800	68.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9810	98.10%
Eye irritation	-	0.9163	91.63%
Skin irritation	-	0.7581	75.81%
Skin corrosion	-	0.9229	92.29%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5549	55.49%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5158	51.58%
skin sensitisation	-	0.8303	83.03%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8040	80.40%
Acute Oral Toxicity (c)	III	0.5868	58.68%
Estrogen receptor binding	+	0.7972	79.72%
Androgen receptor binding	+	0.7503	75.03%
Thyroid receptor binding	+	0.5710	57.10%
Glucocorticoid receptor binding	+	0.6192	61.92%
Aromatase binding	+	0.5841	58.41%
PPAR gamma	+	0.7502	75.02%
Honey bee toxicity	-	0.8535	85.35%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7601	76.01%

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	99.74%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.08%	94.45%
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	94.25%	95.20%
CHEMBL2581	P07339	Cathepsin D	93.89%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.40%	99.15%
CHEMBL5443	O00311	Cell division cycle 7-related protein kinase	93.12%	96.11%
CHEMBL1951	P21397	Monoamine oxidase A	92.15%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.48%	89.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	90.13%	83.10%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.76%	95.56%
CHEMBL4208	P20618	Proteasome component C5	88.74%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.43%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.91%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.56%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.27%	93.04%
CHEMBL2535	P11166	Glucose transporter	85.06%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.84%	99.23%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	84.64%	88.84%
CHEMBL240	Q12809	HERG	84.55%	89.76%
CHEMBL5145	P15056	Serine/threonine-protein kinase B-raf	83.95%	97.90%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.75%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.92%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.35%	93.40%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.84%	85.30%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.69%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	81.41%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.45%	95.89%

Plants that contains it

• Heptapleurum heptaphyllum
• Tribulus terrestris
• Zanthoxylum brachyacanthum

Cross-Links

• PubChem: 9579587
• NPASS: NPC178444
• LOTUS: LTS0214033
• wikiData: Q105265128