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3-[[(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 a6b7d555-5131-463d-8b9a-9f7f383f6e83
Taxonomy Alkaloids and derivatives > Protopine alkaloids
IUPAC Name 3-[[(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/c1-15-9-20-21(12-25(38)39)35(14-17-5-3-6-18(11-17)34(43)44)30-29(27(20)22(36)10-15)32(41)19-7-4-8-24(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 WACNEBDHXGMWLT-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 3-[[(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 - 0.8799 87.99%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.5884 58.84%
OATP2B1 inhibitior - 0.5743 57.43%
OATP1B1 inhibitior + 0.8426 84.26%
OATP1B3 inhibitior + 0.9288 92.88%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7634 76.34%
BSEP inhibitior + 0.9734 97.34%
P-glycoprotein inhibitior + 0.7449 74.49%
P-glycoprotein substrate + 0.7082 70.82%
CYP3A4 substrate + 0.7050 70.50%
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 + 0.6545 65.45%
CYP inhibitory promiscuity - 0.8967 89.67%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4219 42.19%
Eye corrosion - 0.9872 98.72%
Eye irritation - 0.9286 92.86%
Skin irritation - 0.7843 78.43%
Skin corrosion - 0.9382 93.82%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8066 80.66%
Micronuclear + 0.7900 79.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.8451 84.51%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.5653 56.53%
Acute Oral Toxicity (c) III 0.6409 64.09%
Estrogen receptor binding + 0.8093 80.93%
Androgen receptor binding + 0.7283 72.83%
Thyroid receptor binding + 0.5246 52.46%
Glucocorticoid receptor binding + 0.7156 71.56%
Aromatase binding - 0.5876 58.76%
PPAR gamma + 0.7080 70.80%
Honey bee toxicity - 0.7631 76.31%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5700 57.00%
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 99.54% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.81% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 97.25% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.24% 86.33%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 97.13% 97.31%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.34% 96.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 95.99% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.88% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.33% 85.14%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 92.37% 95.17%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 91.32% 96.95%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 91.01% 97.21%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.85% 95.89%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 88.53% 90.71%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 88.06% 93.40%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.44% 97.09%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 86.70% 87.67%
CHEMBL3891 P07384 Calpain 1 86.48% 93.04%
CHEMBL2535 P11166 Glucose transporter 86.41% 98.75%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 85.88% 81.11%
CHEMBL340 P08684 Cytochrome P450 3A4 85.26% 91.19%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.70% 99.17%
CHEMBL5805 Q9NR97 Toll-like receptor 8 84.64% 96.25%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 82.15% 82.38%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 82.04% 99.15%
CHEMBL5028 O14672 ADAM10 81.28% 97.50%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.85% 93.03%
CHEMBL4208 P20618 Proteasome component C5 80.23% 90.00%

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 163114699
LOTUS LTS0133186
wikiData Q105300119