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4-[[(5S)-8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-5-methoxy-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 f9b00e4c-bbdc-43b7-8f14-c75a4ba992cb
Taxonomy Alkaloids and derivatives > Protopine alkaloids
IUPAC Name 4-[[(5S)-8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-5-methoxy-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)OC)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)OC)O)O
InChI InChI=1S/C33H31NO10/c1-15-11-20-25(21(35)12-15)27-28(34(32(20)42-3)14-17-7-9-18(10-8-17)33(40)41)31(39)26-19(30(27)38)5-4-6-23(26)44-24-13-22(36)29(37)16(2)43-24/h4-12,16,22,24,29,32,35-37H,13-14H2,1-3H3,(H,40,41)/t16-,22+,24-,29-,32-/m0/s1
InChI Key ZESVNNLSUFAULI-GCFKKKQCSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C33H31NO10
Molecular Weight 601.60 g/mol
Exact Mass 601.19479619 g/mol
Topological Polar Surface Area (TPSA) 163.00 Ų
XlogP 3.30
Atomic LogP (AlogP) 3.59
H-Bond Acceptor 10
H-Bond Donor 4
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 4-[[(5S)-8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-5-methoxy-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 - 0.5114 51.14%
Caco-2 - 0.8492 84.92%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.5295 52.95%
OATP2B1 inhibitior - 0.5754 57.54%
OATP1B1 inhibitior + 0.8616 86.16%
OATP1B3 inhibitior + 0.9300 93.00%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9580 95.80%
P-glycoprotein inhibitior + 0.7664 76.64%
P-glycoprotein substrate + 0.6582 65.82%
CYP3A4 substrate + 0.7131 71.31%
CYP2C9 substrate - 0.7989 79.89%
CYP2D6 substrate - 0.8749 87.49%
CYP3A4 inhibition - 0.7459 74.59%
CYP2C9 inhibition - 0.7912 79.12%
CYP2C19 inhibition - 0.7741 77.41%
CYP2D6 inhibition - 0.9022 90.22%
CYP1A2 inhibition - 0.7374 73.74%
CYP2C8 inhibition + 0.7068 70.68%
CYP inhibitory promiscuity - 0.9059 90.59%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4412 44.12%
Eye corrosion - 0.9863 98.63%
Eye irritation - 0.9317 93.17%
Skin irritation - 0.7891 78.91%
Skin corrosion - 0.9377 93.77%
Ames mutagenesis + 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7238 72.38%
Micronuclear + 0.7900 79.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.8631 86.31%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.4855 48.55%
Acute Oral Toxicity (c) III 0.6419 64.19%
Estrogen receptor binding + 0.7975 79.75%
Androgen receptor binding + 0.7322 73.22%
Thyroid receptor binding + 0.5523 55.23%
Glucocorticoid receptor binding + 0.7770 77.70%
Aromatase binding - 0.5489 54.89%
PPAR gamma + 0.7039 70.39%
Honey bee toxicity - 0.7417 74.17%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.8143 81.43%

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 99.10% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 98.13% 86.33%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 97.85% 96.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.95% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.37% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 96.35% 91.49%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 95.74% 95.17%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 95.72% 97.31%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 93.79% 97.21%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.63% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 93.49% 95.89%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 92.67% 96.38%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.42% 91.11%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 88.67% 93.40%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 87.93% 96.00%
CHEMBL3891 P07384 Calpain 1 86.72% 93.04%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.67% 97.09%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 86.47% 90.71%
CHEMBL340 P08684 Cytochrome P450 3A4 86.39% 91.19%
CHEMBL2535 P11166 Glucose transporter 86.18% 98.75%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.57% 99.23%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.28% 95.50%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 84.20% 81.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.73% 97.14%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.21% 99.17%
CHEMBL2047 Q96RI1 Bile acid receptor FXR 82.05% 96.10%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.10% 94.00%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 80.12% 87.67%

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 163116130
LOTUS LTS0011653
wikiData Q105373669