PlantaeDB Logo
Login Sign-up

(2S,3S,4R,5R)-2-[(S)-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]-hydroxymethyl]oxane-2,3,4,5-tetrol

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

Top
Internal ID f08b5b1c-7cc6-4fba-93ed-c0884a7485f6
Taxonomy Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
IUPAC Name (2S,3S,4R,5R)-2-[(S)-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]-hydroxymethyl]oxane-2,3,4,5-tetrol
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C27H29NO10/c1-28-21-14(5-4-12-8-18-19(9-15(12)21)37-11-36-18)13-6-7-17(34-2)24(35-3)20(13)22(28)25(31)27(33)26(32)23(30)16(29)10-38-27/h4-9,16,22-23,25-26,29-33H,10-11H2,1-3H3/t16-,22+,23-,25+,26+,27+/m1/s1
InChI Key BPRRWHFNRAGIDG-MSSQBKHLSA-N
Popularity 2 references in papers

Physical and Chemical Properties

Top
Molecular Formula C27H29NO10
Molecular Weight 527.50 g/mol
Exact Mass 527.17914612 g/mol
Topological Polar Surface Area (TPSA) 151.00 Ų
XlogP 1.30
Atomic LogP (AlogP) 0.91
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (2S,3S,4R,5R)-2-[(S)-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]-hydroxymethyl]oxane-2,3,4,5-tetrol

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.7759 77.59%
Caco-2 - 0.7429 74.29%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Lysosomes 0.4801 48.01%
OATP2B1 inhibitior - 0.8625 86.25%
OATP1B1 inhibitior + 0.9132 91.32%
OATP1B3 inhibitior + 0.9470 94.70%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9340 93.40%
P-glycoprotein inhibitior + 0.6120 61.20%
P-glycoprotein substrate + 0.7679 76.79%
CYP3A4 substrate + 0.6621 66.21%
CYP2C9 substrate - 0.7922 79.22%
CYP2D6 substrate - 0.7361 73.61%
CYP3A4 inhibition - 0.7683 76.83%
CYP2C9 inhibition - 0.8112 81.12%
CYP2C19 inhibition - 0.6445 64.45%
CYP2D6 inhibition - 0.7202 72.02%
CYP1A2 inhibition - 0.6495 64.95%
CYP2C8 inhibition + 0.5139 51.39%
CYP inhibitory promiscuity - 0.7432 74.32%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4595 45.95%
Eye corrosion - 0.9874 98.74%
Eye irritation - 0.9402 94.02%
Skin irritation - 0.8045 80.45%
Skin corrosion - 0.9388 93.88%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8675 86.75%
Micronuclear + 0.8100 81.00%
Hepatotoxicity - 0.5500 55.00%
skin sensitisation - 0.8587 85.87%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.8790 87.90%
Acute Oral Toxicity (c) III 0.6757 67.57%
Estrogen receptor binding + 0.8239 82.39%
Androgen receptor binding + 0.7540 75.40%
Thyroid receptor binding + 0.6402 64.02%
Glucocorticoid receptor binding + 0.7618 76.18%
Aromatase binding + 0.6404 64.04%
PPAR gamma + 0.7362 73.62%
Honey bee toxicity - 0.7447 74.47%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity - 0.4589 45.89%

Targets

Top

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.95% 96.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 97.48% 96.77%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 97.23% 89.62%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.77% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.39% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 94.77% 92.62%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.48% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.45% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.08% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.89% 95.89%
CHEMBL2535 P11166 Glucose transporter 90.65% 98.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.43% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.90% 94.45%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.64% 96.00%
CHEMBL5747 Q92793 CREB-binding protein 89.49% 95.12%
CHEMBL4208 P20618 Proteasome component C5 88.91% 90.00%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 88.43% 96.09%
CHEMBL261 P00915 Carbonic anhydrase I 87.53% 96.76%
CHEMBL2413 P32246 C-C chemokine receptor type 1 86.89% 89.50%
CHEMBL344 Q99705 Melanin-concentrating hormone receptor 1 86.60% 92.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.59% 95.56%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 84.24% 97.31%
CHEMBL4225 P49760 Dual specificity protein kinase CLK2 84.21% 80.96%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.88% 100.00%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 80.86% 96.67%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 80.66% 94.42%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.65% 97.25%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.12% 100.00%

Plants that contains it

Top
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.
Macleaya microcarpa

Cross-Links

Top
PubChem 162899046
LOTUS LTS0201049
wikiData Q104943721