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4-[[(5S)-8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1,5-dihydroxy-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 b482ae34-a2ba-4574-b477-c996da7dd016
Taxonomy Alkaloids and derivatives > Protopine alkaloids
IUPAC Name 4-[[(5S)-8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1,5-dihydroxy-3-methyl-7,12-dioxo-5H-benzo[b]phenanthridin-6-yl]methyl]benzoic acid
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C32H29NO10/c1-14-10-19-24(20(34)11-14)26-27(33(31(19)39)13-16-6-8-17(9-7-16)32(40)41)30(38)25-18(29(26)37)4-3-5-22(25)43-23-12-21(35)28(36)15(2)42-23/h3-11,15,21,23,28,31,34-36,39H,12-13H2,1-2H3,(H,40,41)/t15-,21+,23-,28-,31-/m0/s1
InChI Key PTSGKSXSJJYMEF-KQRSIVTKSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C32H29NO10
Molecular Weight 587.60 g/mol
Exact Mass 587.17914612 g/mol
Topological Polar Surface Area (TPSA) 174.00 Ų
XlogP 2.80
Atomic LogP (AlogP) 2.93
H-Bond Acceptor 10
H-Bond Donor 5
Rotatable Bonds 5

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-1,5-dihydroxy-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 + 0.5785 57.85%
Caco-2 - 0.8611 86.11%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.6188 61.88%
OATP2B1 inhibitior - 0.7078 70.78%
OATP1B1 inhibitior + 0.8595 85.95%
OATP1B3 inhibitior + 0.9325 93.25%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8633 86.33%
BSEP inhibitior + 0.9439 94.39%
P-glycoprotein inhibitior + 0.7179 71.79%
P-glycoprotein substrate + 0.6098 60.98%
CYP3A4 substrate + 0.7092 70.92%
CYP2C9 substrate - 0.7989 79.89%
CYP2D6 substrate - 0.8720 87.20%
CYP3A4 inhibition - 0.8008 80.08%
CYP2C9 inhibition - 0.7299 72.99%
CYP2C19 inhibition - 0.6512 65.12%
CYP2D6 inhibition - 0.8874 88.74%
CYP1A2 inhibition - 0.6349 63.49%
CYP2C8 inhibition + 0.6905 69.05%
CYP inhibitory promiscuity - 0.8275 82.75%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.4590 45.90%
Eye corrosion - 0.9871 98.71%
Eye irritation - 0.9258 92.58%
Skin irritation - 0.7909 79.09%
Skin corrosion - 0.9382 93.82%
Ames mutagenesis + 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8057 80.57%
Micronuclear + 0.8100 81.00%
Hepatotoxicity - 0.5000 50.00%
skin sensitisation - 0.8566 85.66%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.4824 48.24%
Acute Oral Toxicity (c) III 0.6477 64.77%
Estrogen receptor binding + 0.7882 78.82%
Androgen receptor binding + 0.7340 73.40%
Thyroid receptor binding + 0.5141 51.41%
Glucocorticoid receptor binding + 0.7022 70.22%
Aromatase binding - 0.6018 60.18%
PPAR gamma + 0.7045 70.45%
Honey bee toxicity - 0.7607 76.07%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.8898 88.98%

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 99.13% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.94% 86.33%
CHEMBL1951 P21397 Monoamine oxidase A 97.29% 91.49%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 97.28% 96.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.67% 95.56%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 95.76% 97.31%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.58% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.69% 89.00%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 93.57% 95.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 93.14% 95.89%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 92.58% 97.21%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 90.32% 96.38%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.02% 91.11%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 87.84% 90.71%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 87.33% 93.40%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.08% 97.09%
CHEMBL3891 P07384 Calpain 1 86.27% 93.04%
CHEMBL4208 P20618 Proteasome component C5 85.97% 90.00%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 84.90% 81.11%
CHEMBL2535 P11166 Glucose transporter 84.87% 98.75%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 84.73% 96.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.45% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 83.76% 91.19%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.35% 95.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.28% 99.17%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 81.71% 96.21%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 81.39% 96.77%
CHEMBL5805 Q9NR97 Toll-like receptor 8 81.27% 96.25%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 81.24% 87.67%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.95% 93.03%
CHEMBL2047 Q96RI1 Bile acid receptor FXR 80.34% 96.10%

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 163112413
LOTUS LTS0223792
wikiData Q105214869