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methyl (9R,12S,13Z,16S,17R,18S)-13-ethylidene-18-hydroxy-8-[[(1S,12S,13R,16R,17R,18R)-16-hydroxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8-tetraen-17-yl]methyl]-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-17-carboxylate

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 eac98a24-95f5-4fcd-bbc0-b5261bae9922
Taxonomy Alkaloids and derivatives > Macroline alkaloids
IUPAC Name methyl (9R,12S,13Z,16S,17R,18S)-13-ethylidene-18-hydroxy-8-[[(1S,12S,13R,16R,17R,18R)-16-hydroxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8-tetraen-17-yl]methyl]-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-17-carboxylate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C42H50N4O5/c1-6-22-19-45-34-17-28(22)42(39(48)50-5)35(45)18-41(38(42)47)27-12-8-10-14-31(27)46(37(34)41)20-29-24-15-33-36-25(23-11-7-9-13-30(23)44(36)4)16-32(43(33)3)26(24)21-51-40(29,2)49/h6-14,24,26,28-29,32-35,37-38,47,49H,15-21H2,1-5H3/b22-6+/t24-,26-,28+,29+,32+,33+,34?,35+,37+,38+,40-,41?,42-/m1/s1
InChI Key KWWPTZADUTXZJC-NQONKIHUSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C42H50N4O5
Molecular Weight 690.90 g/mol
Exact Mass 690.37812071 g/mol
Topological Polar Surface Area (TPSA) 90.60 Ų
XlogP 4.10
Atomic LogP (AlogP) 4.15
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (9R,12S,13Z,16S,17R,18S)-13-ethylidene-18-hydroxy-8-[[(1S,12S,13R,16R,17R,18R)-16-hydroxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8-tetraen-17-yl]methyl]-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-17-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8509 85.09%
Caco-2 - 0.8107 81.07%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.4280 42.80%
OATP2B1 inhibitior - 0.7175 71.75%
OATP1B1 inhibitior + 0.8220 82.20%
OATP1B3 inhibitior + 0.9260 92.60%
MATE1 inhibitior - 0.7400 74.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9841 98.41%
P-glycoprotein inhibitior + 0.8218 82.18%
P-glycoprotein substrate + 0.8411 84.11%
CYP3A4 substrate + 0.7566 75.66%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7491 74.91%
CYP3A4 inhibition - 0.8696 86.96%
CYP2C9 inhibition - 0.7758 77.58%
CYP2C19 inhibition - 0.7450 74.50%
CYP2D6 inhibition - 0.7755 77.55%
CYP1A2 inhibition - 0.7158 71.58%
CYP2C8 inhibition + 0.7753 77.53%
CYP inhibitory promiscuity - 0.5694 56.94%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5406 54.06%
Eye corrosion - 0.9867 98.67%
Eye irritation - 0.9287 92.87%
Skin irritation - 0.7839 78.39%
Skin corrosion - 0.9405 94.05%
Ames mutagenesis + 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7751 77.51%
Micronuclear + 0.7300 73.00%
Hepatotoxicity + 0.5364 53.64%
skin sensitisation - 0.8584 85.84%
Respiratory toxicity + 0.8889 88.89%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.6341 63.41%
Acute Oral Toxicity (c) III 0.5924 59.24%
Estrogen receptor binding + 0.8653 86.53%
Androgen receptor binding + 0.7636 76.36%
Thyroid receptor binding + 0.6222 62.22%
Glucocorticoid receptor binding + 0.7858 78.58%
Aromatase binding + 0.5986 59.86%
PPAR gamma + 0.7852 78.52%
Honey bee toxicity - 0.6894 68.94%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9868 98.68%

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
CHEMBL1914 P06276 Butyrylcholinesterase 99.76% 95.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.02% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 98.75% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.05% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.20% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.13% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.13% 89.00%
CHEMBL2581 P07339 Cathepsin D 93.90% 98.95%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.73% 97.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.60% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.25% 86.33%
CHEMBL240 Q12809 HERG 87.08% 89.76%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.53% 85.14%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 86.14% 95.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.09% 99.23%
CHEMBL217 P14416 Dopamine D2 receptor 85.19% 95.62%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.53% 82.69%
CHEMBL2535 P11166 Glucose transporter 84.22% 98.75%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.65% 91.07%
CHEMBL3922 P50579 Methionine aminopeptidase 2 82.49% 97.28%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 81.24% 96.39%
CHEMBL1951 P21397 Monoamine oxidase A 81.02% 91.49%
CHEMBL5028 O14672 ADAM10 80.74% 97.50%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 80.15% 96.67%
CHEMBL340 P08684 Cytochrome P450 3A4 80.14% 91.19%

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.
Alstonia macrophylla

Cross-Links

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PubChem 101938433
LOTUS LTS0020591
wikiData Q105147190