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4-[[(5S)-5-(carboxymethyl)-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 b5210c09-c4f9-4e5f-a593-154f9fee6ba5
Taxonomy Alkaloids and derivatives > Protopine alkaloids
IUPAC Name 4-[[(5S)-5-(carboxymethyl)-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)
SMILES (Isomeric)
InChI InChI=1S/C34H31NO11/c1-15-10-20-21(12-25(38)39)35(14-17-6-8-18(9-7-17)34(43)44)30-29(27(20)22(36)11-15)32(41)19-4-3-5-24(28(19)33(30)42)46-26-13-23(37)31(40)16(2)45-26/h3-11,16,21,23,26,31,36-37,40H,12-14H2,1-2H3,(H,38,39)(H,43,44)/t16-,21-,23+,26-,31-/m0/s1
InChI Key FZJZXCFECKIYEK-ILDYLSGOSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C34H31NO11
Molecular Weight 629.60 g/mol
Exact Mass 629.18971080 g/mol
Topological Polar Surface Area (TPSA) 191.00 Ų
XlogP 2.90
Atomic LogP (AlogP) 3.46
H-Bond Acceptor 10
H-Bond Donor 5
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 4-[[(5S)-5-(carboxymethyl)-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 - 0.8765 87.65%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.5884 58.84%
OATP2B1 inhibitior - 0.5717 57.17%
OATP1B1 inhibitior + 0.8451 84.51%
OATP1B3 inhibitior + 0.9288 92.88%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7634 76.34%
BSEP inhibitior + 0.9685 96.85%
P-glycoprotein inhibitior + 0.7461 74.61%
P-glycoprotein substrate + 0.6680 66.80%
CYP3A4 substrate + 0.7118 71.18%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8405 84.05%
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 + 0.7193 71.93%
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 - 0.9287 92.87%
Skin irritation - 0.7843 78.43%
Skin corrosion - 0.9382 93.82%
Ames mutagenesis + 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7300 73.00%
Micronuclear + 0.7900 79.00%
Hepatotoxicity - 0.5000 50.00%
skin sensitisation - 0.8451 84.51%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.4509 45.09%
Acute Oral Toxicity (c) III 0.6409 64.09%
Estrogen receptor binding + 0.8222 82.22%
Androgen receptor binding + 0.7695 76.95%
Thyroid receptor binding + 0.5141 51.41%
Glucocorticoid receptor binding + 0.7160 71.60%
Aromatase binding - 0.5894 58.94%
PPAR gamma + 0.6915 69.15%
Honey bee toxicity - 0.7548 75.48%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6100 61.00%
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 99.31% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 98.06% 86.33%
CHEMBL1951 P21397 Monoamine oxidase A 97.57% 91.49%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 97.45% 97.31%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.39% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.09% 96.09%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 95.54% 95.17%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 95.06% 93.40%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.79% 89.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 93.86% 96.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.63% 95.89%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 89.52% 97.21%
CHEMBL4208 P20618 Proteasome component C5 88.49% 90.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 87.77% 90.71%
CHEMBL3891 P07384 Calpain 1 87.76% 93.04%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 86.96% 81.11%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 86.89% 87.67%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.77% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 86.40% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.32% 97.09%
CHEMBL2535 P11166 Glucose transporter 84.99% 98.75%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 84.83% 96.21%
CHEMBL5805 Q9NR97 Toll-like receptor 8 83.90% 96.25%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.62% 95.50%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 83.52% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 82.83% 85.14%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 82.55% 96.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.15% 99.17%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.58% 96.90%
CHEMBL5028 O14672 ADAM10 80.41% 97.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.22% 97.14%
CHEMBL3194 P02766 Transthyretin 80.20% 90.71%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 80.16% 80.78%

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.
There are no matching plants.

Cross-Links

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PubChem 163108846
LOTUS LTS0161083
wikiData Q105004983