methyl (1R,9R,10R,13S,14R,15R,20S)-9,14,15-trihydroxy-6-methoxy-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2(7),3,5-triene-10-carboxylate

Details

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Internal ID cd55d69b-6770-437d-b603-2ecf3706535f
Taxonomy Alkaloids and derivatives > Aspidospermatan-type alkaloids
IUPAC Name methyl (1R,9R,10R,13S,14R,15R,20S)-9,14,15-trihydroxy-6-methoxy-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2(7),3,5-triene-10-carboxylate
SMILES (Canonical) COC1=CC=CC2=C1NC3(C24CCN5C4C6(CCC3(C6)C(=O)OC)C(C(C5)O)O)O
SMILES (Isomeric) COC1=CC=CC2=C1N[C@]3([C@]24CCN5[C@H]4[C@@]6(CC[C@]3(C6)C(=O)OC)[C@H]([C@@H](C5)O)O)O
InChI InChI=1S/C22H28N2O6/c1-29-14-5-3-4-12-15(14)23-22(28)20(18(27)30-2)7-6-19(11-20)16(26)13(25)10-24-9-8-21(12,22)17(19)24/h3-5,13,16-17,23,25-26,28H,6-11H2,1-2H3/t13-,16+,17+,19-,20+,21-,22+/m1/s1
InChI Key GNXKRDYLQPMSRO-DAZHGGCQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H28N2O6
Molecular Weight 416.50 g/mol
Exact Mass 416.19473662 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 0.20
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1R,9R,10R,13S,14R,15R,20S)-9,14,15-trihydroxy-6-methoxy-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2(7),3,5-triene-10-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6089 60.89%
Caco-2 - 0.5319 53.19%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.6490 64.90%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9336 93.36%
OATP1B3 inhibitior + 0.9381 93.81%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.4568 45.68%
P-glycoprotein inhibitior - 0.8068 80.68%
P-glycoprotein substrate + 0.6626 66.26%
CYP3A4 substrate + 0.6947 69.47%
CYP2C9 substrate - 0.8032 80.32%
CYP2D6 substrate + 0.4282 42.82%
CYP3A4 inhibition - 0.7840 78.40%
CYP2C9 inhibition - 0.8362 83.62%
CYP2C19 inhibition - 0.7913 79.13%
CYP2D6 inhibition - 0.7972 79.72%
CYP1A2 inhibition - 0.8574 85.74%
CYP2C8 inhibition - 0.7313 73.13%
CYP inhibitory promiscuity - 0.9410 94.10%
UGT catelyzed - 0.8000 80.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.6031 60.31%
Eye corrosion - 0.9880 98.80%
Eye irritation - 0.9816 98.16%
Skin irritation - 0.7774 77.74%
Skin corrosion - 0.9371 93.71%
Ames mutagenesis - 0.6778 67.78%
Human Ether-a-go-go-Related Gene inhibition - 0.4259 42.59%
Micronuclear + 0.7800 78.00%
Hepatotoxicity + 0.5791 57.91%
skin sensitisation - 0.8561 85.61%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 1.0000 100.00%
Mitochondrial toxicity + 0.9500 95.00%
Nephrotoxicity + 0.4727 47.27%
Acute Oral Toxicity (c) III 0.5395 53.95%
Estrogen receptor binding + 0.7152 71.52%
Androgen receptor binding + 0.8052 80.52%
Thyroid receptor binding + 0.5351 53.51%
Glucocorticoid receptor binding + 0.5512 55.12%
Aromatase binding + 0.7518 75.18%
PPAR gamma - 0.5528 55.28%
Honey bee toxicity - 0.8847 88.47%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.6687 66.87%

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 99.36% 96.09%
CHEMBL4040 P28482 MAP kinase ERK2 96.77% 83.82%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.09% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.59% 94.45%
CHEMBL2581 P07339 Cathepsin D 93.79% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.49% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.10% 95.89%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.26% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.33% 86.33%
CHEMBL5028 O14672 ADAM10 87.04% 97.50%
CHEMBL2535 P11166 Glucose transporter 85.46% 98.75%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 85.03% 93.03%
CHEMBL4208 P20618 Proteasome component C5 84.82% 90.00%
CHEMBL340 P08684 Cytochrome P450 3A4 84.00% 91.19%
CHEMBL238 Q01959 Dopamine transporter 82.40% 95.88%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.32% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.27% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 81.67% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.47% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.91% 97.14%

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.
Kopsia fruticosa

Cross-Links

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PubChem 12116553
LOTUS LTS0247810
wikiData Q105013435