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3-[[(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 34759dd7-b0ee-4573-8d19-8e89a93f5459
Taxonomy Alkaloids and derivatives > Protopine alkaloids
IUPAC Name 3-[[(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(=CC=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(=CC=C6)C(=O)O)OC)O)O
InChI InChI=1S/C33H31NO10/c1-15-10-20-25(21(35)11-15)27-28(34(32(20)42-3)14-17-6-4-7-18(12-17)33(40)41)31(39)26-19(30(27)38)8-5-9-23(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 VVUDBVKCWBSLKB-GCFKKKQCSA-N
Popularity 0 references 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 3-[[(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 - 0.8631 86.31%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.5295 52.95%
OATP2B1 inhibitior - 0.5768 57.68%
OATP1B1 inhibitior + 0.8587 85.87%
OATP1B3 inhibitior + 0.9300 93.00%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9746 97.46%
P-glycoprotein inhibitior + 0.7470 74.70%
P-glycoprotein substrate + 0.7005 70.05%
CYP3A4 substrate + 0.7054 70.54%
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 + 0.6401 64.01%
CYP inhibitory promiscuity - 0.9059 90.59%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4412 44.12%
Eye corrosion - 0.9863 98.63%
Eye irritation - 0.9309 93.09%
Skin irritation - 0.7891 78.91%
Skin corrosion - 0.9377 93.77%
Ames mutagenesis + 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7169 71.69%
Micronuclear + 0.7900 79.00%
Hepatotoxicity + 0.5375 53.75%
skin sensitisation - 0.8631 86.31%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.4686 46.86%
Acute Oral Toxicity (c) III 0.6419 64.19%
Estrogen receptor binding + 0.8178 81.78%
Androgen receptor binding + 0.6744 67.44%
Thyroid receptor binding + 0.5657 56.57%
Glucocorticoid receptor binding + 0.7710 77.10%
Aromatase binding - 0.5531 55.31%
PPAR gamma + 0.7246 72.46%
Honey bee toxicity - 0.7510 75.10%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5700 57.00%
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 99.40% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.33% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.15% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.95% 95.56%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 96.91% 96.95%
CHEMBL1951 P21397 Monoamine oxidase A 95.88% 91.49%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 95.24% 99.23%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 95.21% 97.31%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.95% 89.00%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 94.71% 97.21%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.11% 85.14%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 92.70% 95.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 92.07% 95.89%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 88.27% 96.38%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.77% 97.09%
CHEMBL2535 P11166 Glucose transporter 87.51% 98.75%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 87.30% 90.71%
CHEMBL3891 P07384 Calpain 1 85.35% 93.04%
CHEMBL340 P08684 Cytochrome P450 3A4 85.25% 91.19%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.75% 99.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.86% 95.89%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 82.97% 96.00%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 82.94% 81.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.72% 97.14%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.53% 93.03%
CHEMBL5028 O14672 ADAM10 80.26% 97.50%

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 163114641
LOTUS LTS0206888
wikiData Q105297893