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(1S)-1-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]ethanol

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 4d044b9b-f41d-475c-8c7e-84cd6202cdd0
Taxonomy Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
IUPAC Name (1S)-1-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]ethanol
SMILES (Canonical) CC(C1C2=C(C=CC(=C2OC)OC)C3=C(N1C)C4=CC5=C(C=C4C=C3)OCO5)O
SMILES (Isomeric) C[C@@H]([C@@H]1C2=C(C=CC(=C2OC)OC)C3=C(N1C)C4=CC5=C(C=C4C=C3)OCO5)O
InChI InChI=1S/C23H23NO5/c1-12(25)21-20-14(7-8-17(26-3)23(20)27-4)15-6-5-13-9-18-19(29-11-28-18)10-16(13)22(15)24(21)2/h5-10,12,21,25H,11H2,1-4H3/t12-,21+/m0/s1
InChI Key KGXGGTSECNVCSW-LAJNKCICSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H23NO5
Molecular Weight 393.40 g/mol
Exact Mass 393.15762283 g/mol
Topological Polar Surface Area (TPSA) 60.40 Ų
XlogP 4.00
Atomic LogP (AlogP) 4.12
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S)-1-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]ethanol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7851 78.51%
Caco-2 + 0.8429 84.29%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.4560 45.60%
OATP2B1 inhibitior - 0.8732 87.32%
OATP1B1 inhibitior + 0.9291 92.91%
OATP1B3 inhibitior + 0.9398 93.98%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9163 91.63%
P-glycoprotein inhibitior + 0.8051 80.51%
P-glycoprotein substrate + 0.5737 57.37%
CYP3A4 substrate + 0.5628 56.28%
CYP2C9 substrate - 0.8100 81.00%
CYP2D6 substrate + 0.4735 47.35%
CYP3A4 inhibition + 0.7743 77.43%
CYP2C9 inhibition - 0.5608 56.08%
CYP2C19 inhibition + 0.9128 91.28%
CYP2D6 inhibition + 0.6961 69.61%
CYP1A2 inhibition + 0.8497 84.97%
CYP2C8 inhibition - 0.5993 59.93%
CYP inhibitory promiscuity + 0.7612 76.12%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4348 43.48%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9586 95.86%
Skin irritation - 0.8144 81.44%
Skin corrosion - 0.9551 95.51%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6761 67.61%
Micronuclear + 0.7700 77.00%
Hepatotoxicity - 0.5000 50.00%
skin sensitisation - 0.8751 87.51%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.9188 91.88%
Acute Oral Toxicity (c) III 0.7621 76.21%
Estrogen receptor binding + 0.8469 84.69%
Androgen receptor binding + 0.7557 75.57%
Thyroid receptor binding + 0.7957 79.57%
Glucocorticoid receptor binding + 0.8218 82.18%
Aromatase binding + 0.5936 59.36%
PPAR gamma + 0.7491 74.91%
Honey bee toxicity - 0.8577 85.77%
Biodegradation - 1.0000 100.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.7568 75.68%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.51% 96.09%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 95.76% 96.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 95.71% 96.77%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 95.10% 92.62%
CHEMBL2581 P07339 Cathepsin D 94.54% 98.95%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 92.85% 89.62%
CHEMBL261 P00915 Carbonic anhydrase I 90.28% 96.76%
CHEMBL2535 P11166 Glucose transporter 89.31% 98.75%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.87% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.54% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.09% 86.33%
CHEMBL4208 P20618 Proteasome component C5 87.97% 90.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.68% 94.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.37% 91.11%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.30% 95.89%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.33% 96.00%
CHEMBL5747 Q92793 CREB-binding protein 86.20% 95.12%
CHEMBL344 Q99705 Melanin-concentrating hormone receptor 1 84.73% 92.50%
CHEMBL2413 P32246 C-C chemokine receptor type 1 84.40% 89.50%
CHEMBL213 P08588 Beta-1 adrenergic receptor 84.23% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.09% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.64% 94.45%
CHEMBL4835 P00338 L-lactate dehydrogenase A chain 83.52% 95.34%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.51% 99.17%
CHEMBL4040 P28482 MAP kinase ERK2 83.28% 83.82%
CHEMBL3492 P49721 Proteasome Macropain subunit 81.56% 90.24%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.27% 90.71%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 80.15% 89.44%

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.
Macleaya microcarpa

Cross-Links

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PubChem 162960851
LOTUS LTS0033152
wikiData Q105141025