3-Methoxy-5-methyl-3,4,4a,5,6,6a-hexahydro-8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indol-8-ol

Details

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Internal ID b1e42a1a-0139-48c1-bacb-fb40b122099c
Taxonomy Alkaloids and derivatives > Amaryllidaceae alkaloids > Tazettine-type amaryllidaceae alkaloids
IUPAC Name 18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.01,16.02,10.04,8]icosa-2,4(8),9,19-tetraen-11-ol
SMILES (Canonical) CN1CC2C3(C1CC(C=C3)OC)C4=CC5=C(C=C4C(O2)O)OCO5
SMILES (Isomeric) CN1CC2C3(C1CC(C=C3)OC)C4=CC5=C(C=C4C(O2)O)OCO5
InChI InChI=1S/C18H21NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-17,20H,5,8-9H2,1-2H3
InChI Key KLJOYDMUWKSYBP-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C18H21NO5
Molecular Weight 331.40 g/mol
Exact Mass 331.14197277 g/mol
Topological Polar Surface Area (TPSA) 60.40 Ų
XlogP 1.30
Atomic LogP (AlogP) 1.33
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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KLJOYDMUWKSYBP-UHFFFAOYSA-N
NCI60_000235
3-Methoxy-5-methyl-3,4,4a,5,6,6a-hexahydro-8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indol-8-ol #

2D Structure

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2D Structure of 3-Methoxy-5-methyl-3,4,4a,5,6,6a-hexahydro-8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indol-8-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9035 90.35%
Caco-2 + 0.8724 87.24%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Lysosomes 0.5159 51.59%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9218 92.18%
OATP1B3 inhibitior + 0.9452 94.52%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.5731 57.31%
P-glycoprotein inhibitior - 0.8024 80.24%
P-glycoprotein substrate - 0.5464 54.64%
CYP3A4 substrate + 0.6474 64.74%
CYP2C9 substrate - 0.6194 61.94%
CYP2D6 substrate + 0.4339 43.39%
CYP3A4 inhibition - 0.8731 87.31%
CYP2C9 inhibition - 0.9035 90.35%
CYP2C19 inhibition + 0.5061 50.61%
CYP2D6 inhibition + 0.6426 64.26%
CYP1A2 inhibition - 0.7264 72.64%
CYP2C8 inhibition - 0.8676 86.76%
CYP inhibitory promiscuity - 0.6235 62.35%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5639 56.39%
Eye corrosion - 0.9881 98.81%
Eye irritation - 0.9770 97.70%
Skin irritation - 0.7906 79.06%
Skin corrosion - 0.9380 93.80%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7892 78.92%
Micronuclear + 0.6200 62.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.8160 81.60%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity - 0.6440 64.40%
Acute Oral Toxicity (c) III 0.7311 73.11%
Estrogen receptor binding + 0.6702 67.02%
Androgen receptor binding + 0.6454 64.54%
Thyroid receptor binding + 0.7191 71.91%
Glucocorticoid receptor binding + 0.6498 64.98%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.6574 65.74%
Honey bee toxicity - 0.7715 77.15%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.8475 84.75%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.78% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.77% 96.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 98.40% 96.77%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.19% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.20% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.00% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.27% 97.25%
CHEMBL4208 P20618 Proteasome component C5 88.87% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.46% 89.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.25% 92.62%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 85.20% 93.40%
CHEMBL230 P35354 Cyclooxygenase-2 85.14% 89.63%
CHEMBL2581 P07339 Cathepsin D 84.55% 98.95%
CHEMBL4040 P28482 MAP kinase ERK2 84.48% 83.82%
CHEMBL4225 P49760 Dual specificity protein kinase CLK2 84.24% 80.96%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.69% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.29% 95.56%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 81.95% 89.62%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.70% 95.89%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 81.64% 82.38%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.37% 90.71%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.87% 100.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 80.64% 89.50%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 80.45% 91.03%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.11% 91.07%

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.
Cyrtanthus obliquus
Hippeastrum morelianum
Hymenocallis littoralis
Hymenocallis rotata
Lycoris radiata
Narcissus confusus
Narcissus tazetta
Pancratium biflorum
Sprekelia formosissima

Cross-Links

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PubChem 419046
LOTUS LTS0225302
wikiData Q105142656