Bastadin-21

Details

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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

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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

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(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

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2D Structure of Bastadin-21

3D Structure

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ADMET Properties (via admetSAR 2)

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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

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Heptapleurum heptaphyllum
Tribulus terrestris
Zanthoxylum brachyacanthum

Cross-Links

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PubChem 9579587
NPASS NPC178444
LOTUS LTS0214033
wikiData Q105265128