(1S,12S,13R,16S,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazahexacyclo[10.10.1.02,10.04,9.013,21.016,20]tricosa-2(10),4,6,8-tetraen-18-one

Details

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Internal ID 3ab16248-d34a-44b8-8ca4-927dfd45de8d
Taxonomy Alkaloids and derivatives > Macroline alkaloids
IUPAC Name (1S,12S,13R,16S,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazahexacyclo[10.10.1.02,10.04,9.013,21.016,20]tricosa-2(10),4,6,8-tetraen-18-one
SMILES (Canonical) CC12C(CC(=O)O1)C3CC4C5=C(CC(C3CO2)N4C)C6=CC=CC=C6N5C
SMILES (Isomeric) C[C@@]12[C@@H](CC(=O)O1)[C@@H]3C[C@H]4C5=C(C[C@@H]([C@@H]3CO2)N4C)C6=CC=CC=C6N5C
InChI InChI=1S/C22H26N2O3/c1-22-16(10-20(25)27-22)13-8-19-21-14(9-18(23(19)2)15(13)11-26-22)12-6-4-5-7-17(12)24(21)3/h4-7,13,15-16,18-19H,8-11H2,1-3H3/t13-,15-,16+,18+,19+,22+/m1/s1
InChI Key HIJSJXVEJVBFFC-ZPPAPSBDSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H26N2O3
Molecular Weight 366.50 g/mol
Exact Mass 366.19434270 g/mol
Topological Polar Surface Area (TPSA) 43.70 Ų
XlogP 2.50
Atomic LogP (AlogP) 3.02
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,12S,13R,16S,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazahexacyclo[10.10.1.02,10.04,9.013,21.016,20]tricosa-2(10),4,6,8-tetraen-18-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9695 96.95%
Caco-2 + 0.6947 69.47%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Lysosomes 0.5346 53.46%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9059 90.59%
OATP1B3 inhibitior + 0.9332 93.32%
MATE1 inhibitior - 0.6400 64.00%
OCT2 inhibitior - 0.5250 52.50%
BSEP inhibitior + 0.6366 63.66%
P-glycoprotein inhibitior - 0.4521 45.21%
P-glycoprotein substrate + 0.6780 67.80%
CYP3A4 substrate + 0.7148 71.48%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7063 70.63%
CYP3A4 inhibition - 0.7355 73.55%
CYP2C9 inhibition - 0.9359 93.59%
CYP2C19 inhibition - 0.7549 75.49%
CYP2D6 inhibition - 0.8123 81.23%
CYP1A2 inhibition - 0.6399 63.99%
CYP2C8 inhibition + 0.4566 45.66%
CYP inhibitory promiscuity - 0.7890 78.90%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6281 62.81%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9910 99.10%
Skin irritation - 0.8367 83.67%
Skin corrosion - 0.9548 95.48%
Ames mutagenesis + 0.5946 59.46%
Human Ether-a-go-go-Related Gene inhibition + 0.9167 91.67%
Micronuclear + 0.6100 61.00%
Hepatotoxicity + 0.5988 59.88%
skin sensitisation - 0.8802 88.02%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.9250 92.50%
Nephrotoxicity + 0.5000 50.00%
Acute Oral Toxicity (c) III 0.5918 59.18%
Estrogen receptor binding + 0.8718 87.18%
Androgen receptor binding + 0.6969 69.69%
Thyroid receptor binding + 0.7387 73.87%
Glucocorticoid receptor binding + 0.8200 82.00%
Aromatase binding + 0.6913 69.13%
PPAR gamma - 0.5119 51.19%
Honey bee toxicity - 0.7390 73.90%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.6500 65.00%
Fish aquatic toxicity + 0.8260 82.60%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.49% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.21% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.07% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.05% 89.00%
CHEMBL2581 P07339 Cathepsin D 95.46% 98.95%
CHEMBL1951 P21397 Monoamine oxidase A 92.68% 91.49%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.81% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.37% 96.09%
CHEMBL2265 P23141 Acyl coenzyme A:cholesterol acyltransferase 89.78% 85.94%
CHEMBL3192 Q9BY41 Histone deacetylase 8 89.70% 93.99%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.30% 99.23%
CHEMBL1899 P46098 Serotonin 3a (5-HT3a) receptor 87.22% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.11% 82.69%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 85.81% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.14% 97.14%
CHEMBL240 Q12809 HERG 84.05% 89.76%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 83.80% 96.67%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 83.50% 85.11%
CHEMBL255 P29275 Adenosine A2b receptor 83.24% 98.59%
CHEMBL5103 Q969S8 Histone deacetylase 10 82.37% 90.08%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.18% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.39% 97.09%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 80.26% 93.65%
CHEMBL2535 P11166 Glucose transporter 80.10% 98.75%
CHEMBL2095172 P14867 GABA-A receptor; alpha-1/beta-2/gamma-2 80.08% 92.67%

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 angustifolia

Cross-Links

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PubChem 118715142
LOTUS LTS0070853
wikiData Q105028883