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4-[[(5S)-5-(2-carboxy-2-oxoethyl)-8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-3-methyl-7,12-dioxo-5H-benzo[b]phenanthridin-6-yl]methyl]benzoic acid

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID f4077b94-ebfc-46af-945f-84a890a5e251
Taxonomy Alkaloids and derivatives > Protopine alkaloids
IUPAC Name 4-[[(5S)-5-(2-carboxy-2-oxoethyl)-8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-3-methyl-7,12-dioxo-5H-benzo[b]phenanthridin-6-yl]methyl]benzoic acid
SMILES (Canonical) CC1C(C(CC(O1)OC2=CC=CC3=C2C(=O)C4=C(C3=O)C5=C(C=C(C=C5O)C)C(N4CC6=CC=C(C=C6)C(=O)O)CC(=O)C(=O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@@H](C[C@@H](O1)OC2=CC=CC3=C2C(=O)C4=C(C3=O)C5=C(C=C(C=C5O)C)[C@@H](N4CC6=CC=C(C=C6)C(=O)O)CC(=O)C(=O)O)O)O
InChI InChI=1S/C35H31NO12/c1-15-10-20-21(12-24(39)35(45)46)36(14-17-6-8-18(9-7-17)34(43)44)30-29(27(20)22(37)11-15)32(41)19-4-3-5-25(28(19)33(30)42)48-26-13-23(38)31(40)16(2)47-26/h3-11,16,21,23,26,31,37-38,40H,12-14H2,1-2H3,(H,43,44)(H,45,46)/t16-,21-,23+,26-,31-/m0/s1
InChI Key OURXYGSYQVWUFL-ILDYLSGOSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C35H31NO12
Molecular Weight 657.60 g/mol
Exact Mass 657.18462542 g/mol
Topological Polar Surface Area (TPSA) 208.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 3.03
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 4-[[(5S)-5-(2-carboxy-2-oxoethyl)-8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-3-methyl-7,12-dioxo-5H-benzo[b]phenanthridin-6-yl]methyl]benzoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6940 69.40%
Caco-2 - 0.8706 87.06%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.5884 58.84%
OATP2B1 inhibitior - 0.5721 57.21%
OATP1B1 inhibitior + 0.8498 84.98%
OATP1B3 inhibitior + 0.9288 92.88%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7634 76.34%
BSEP inhibitior + 0.9622 96.22%
P-glycoprotein inhibitior + 0.7612 76.12%
P-glycoprotein substrate + 0.6928 69.28%
CYP3A4 substrate + 0.7067 70.67%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8416 84.16%
CYP3A4 inhibition - 0.8452 84.52%
CYP2C9 inhibition - 0.7984 79.84%
CYP2C19 inhibition - 0.7711 77.11%
CYP2D6 inhibition - 0.8259 82.59%
CYP1A2 inhibition - 0.5782 57.82%
CYP2C8 inhibition + 0.7414 74.14%
CYP inhibitory promiscuity - 0.8967 89.67%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4219 42.19%
Eye corrosion - 0.9872 98.72%
Eye irritation - 0.9250 92.50%
Skin irritation - 0.7843 78.43%
Skin corrosion - 0.9382 93.82%
Ames mutagenesis + 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7297 72.97%
Micronuclear + 0.7900 79.00%
Hepatotoxicity + 0.5500 55.00%
skin sensitisation - 0.8451 84.51%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.4576 45.76%
Acute Oral Toxicity (c) III 0.6409 64.09%
Estrogen receptor binding + 0.8217 82.17%
Androgen receptor binding + 0.7700 77.00%
Thyroid receptor binding - 0.4877 48.77%
Glucocorticoid receptor binding + 0.7151 71.51%
Aromatase binding - 0.5910 59.10%
PPAR gamma + 0.6835 68.35%
Honey bee toxicity - 0.7560 75.60%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9470 94.70%

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
CHEMBL2581 P07339 Cathepsin D 99.11% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 98.49% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 98.32% 95.56%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 98.01% 97.31%
CHEMBL1951 P21397 Monoamine oxidase A 97.27% 91.49%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 97.17% 95.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.85% 96.09%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 94.47% 96.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.44% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 94.13% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.27% 97.09%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 91.08% 93.40%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 90.31% 90.71%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 87.25% 80.78%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 87.04% 96.21%
CHEMBL3891 P07384 Calpain 1 86.85% 93.04%
CHEMBL4208 P20618 Proteasome component C5 86.83% 90.00%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 85.44% 97.21%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 84.46% 96.00%
CHEMBL226 P30542 Adenosine A1 receptor 84.42% 95.93%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.07% 99.23%
CHEMBL2535 P11166 Glucose transporter 83.83% 98.75%
CHEMBL340 P08684 Cytochrome P450 3A4 83.79% 91.19%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.67% 99.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 83.53% 91.11%
CHEMBL5805 Q9NR97 Toll-like receptor 8 81.46% 96.25%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 163112047
LOTUS LTS0187448
wikiData Q105200379