Ajaconine

Details

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Internal ID f17cb4a0-313a-49fa-b08e-ae11b9d4bb66
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids
IUPAC Name (1S,5R,10R,11S,12R,14S,16R,17R)-7-(2-hydroxyethyl)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.211,14.01,8.05,17.011,16]icosan-12-ol
SMILES (Canonical) CC12CCCC34C1CC(C56C3CC(CC5)C(=C)C6O)OC4N(C2)CCO
SMILES (Isomeric) C[C@@]12CCC[C@]34[C@@H]1C[C@H]([C@]56[C@H]3C[C@H](CC5)C(=C)[C@H]6O)OC4N(C2)CCO
InChI InChI=1S/C22H33NO3/c1-13-14-4-7-22(18(13)25)16(10-14)21-6-3-5-20(2)12-23(8-9-24)19(21)26-17(22)11-15(20)21/h14-19,24-25H,1,3-12H2,2H3/t14-,15+,16-,17+,18+,19?,20-,21-,22+/m0/s1
InChI Key RLXRCZIALRMBJR-VRMMQTGXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H33NO3
Molecular Weight 359.50 g/mol
Exact Mass 359.24604391 g/mol
Topological Polar Surface Area (TPSA) 52.90 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.55
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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7alpha,20-epoxy-21-(2-hydroxyethyl)-4-methylatid-16-en-15beta-ol
545-61-9
CHEBI:2523
SCHEMBL8196814
C08656
Q27105702
(1S,5R,10R,11S,12R,14S,16R,17R)-7-(2-hydroxyethyl)-5-methyl-13-methylidene-9-oxa-7-azahexacyclo[8.6.2.211,14.01,8.05,17.011,16]icosan-12-ol

2D Structure

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2D Structure of Ajaconine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9611 96.11%
Caco-2 + 0.5719 57.19%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Lysosomes 0.5103 51.03%
OATP2B1 inhibitior - 0.8580 85.80%
OATP1B1 inhibitior + 0.8650 86.50%
OATP1B3 inhibitior + 0.9442 94.42%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior - 0.6896 68.96%
P-glycoprotein inhibitior - 0.8744 87.44%
P-glycoprotein substrate - 0.5439 54.39%
CYP3A4 substrate + 0.6729 67.29%
CYP2C9 substrate - 0.8075 80.75%
CYP2D6 substrate - 0.7422 74.22%
CYP3A4 inhibition - 0.7346 73.46%
CYP2C9 inhibition - 0.9005 90.05%
CYP2C19 inhibition - 0.7551 75.51%
CYP2D6 inhibition - 0.8858 88.58%
CYP1A2 inhibition - 0.8460 84.60%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.9464 94.64%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5004 50.04%
Eye corrosion - 0.9833 98.33%
Eye irritation - 0.9002 90.02%
Skin irritation - 0.7369 73.69%
Skin corrosion - 0.8828 88.28%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8336 83.36%
Micronuclear - 0.5200 52.00%
Hepatotoxicity - 0.5511 55.11%
skin sensitisation - 0.8312 83.12%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.7997 79.97%
Acute Oral Toxicity (c) III 0.5747 57.47%
Estrogen receptor binding + 0.7611 76.11%
Androgen receptor binding + 0.6571 65.71%
Thyroid receptor binding + 0.6526 65.26%
Glucocorticoid receptor binding + 0.6647 66.47%
Aromatase binding + 0.6556 65.56%
PPAR gamma - 0.5000 50.00%
Honey bee toxicity - 0.8535 85.35%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity - 0.4663 46.63%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.36% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.00% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.61% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 94.32% 95.93%
CHEMBL2140 P48775 Tryptophan 2,3-dioxygenase 92.28% 98.46%
CHEMBL237 P41145 Kappa opioid receptor 89.63% 98.10%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.60% 97.09%
CHEMBL2581 P07339 Cathepsin D 88.34% 98.95%
CHEMBL238 Q01959 Dopamine transporter 87.73% 95.88%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.53% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 85.32% 95.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.22% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.60% 95.89%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.34% 92.62%
CHEMBL5555 O00767 Acyl-CoA desaturase 83.19% 97.50%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 82.31% 97.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.85% 86.33%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 80.71% 90.24%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.10% 93.04%
CHEMBL3192 Q9BY41 Histone deacetylase 8 80.06% 93.99%

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.
Delphinium brunonianum
Delphinium delavayi
Delphinium elatum
Delphinium tatsienense

Cross-Links

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PubChem 441706
LOTUS LTS0204547
wikiData Q27105702