R-(-)-actinodaphnine

Details

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Internal ID 3d33b03a-a3f0-4bff-ba72-f164dd7e6e8e
Taxonomy Alkaloids and derivatives > Aporphines
IUPAC Name (12R)-17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaen-16-ol
SMILES (Canonical) COC1=C(C=C2CC3C4=C(C2=C1)C5=C(C=C4CCN3)OCO5)O
SMILES (Isomeric) COC1=C(C=C2C[C@@H]3C4=C(C2=C1)C5=C(C=C4CCN3)OCO5)O
InChI InChI=1S/C18H17NO4/c1-21-14-7-11-10(5-13(14)20)4-12-16-9(2-3-19-12)6-15-18(17(11)16)23-8-22-15/h5-7,12,19-20H,2-4,8H2,1H3/t12-/m1/s1
InChI Key VYJUHRAQPIBWNV-GFCCVEGCSA-N
Popularity 6 references in papers

Physical and Chemical Properties

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Molecular Formula C18H17NO4
Molecular Weight 311.30 g/mol
Exact Mass 311.11575802 g/mol
Topological Polar Surface Area (TPSA) 60.00 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.54
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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MLS000574934
CHEBI:70638
SMR000156298
CHEMBL1588263
BDBM50136
cid_11957301
DTXSID101121123
HMS2218M06
NCGC00247613-01
Q27138971
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of R-(-)-actinodaphnine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9540 95.40%
Caco-2 + 0.7636 76.36%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability + 0.5286 52.86%
Subcellular localzation Mitochondria 0.5361 53.61%
OATP2B1 inhibitior - 0.8556 85.56%
OATP1B1 inhibitior + 0.9054 90.54%
OATP1B3 inhibitior + 0.9531 95.31%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.6980 69.80%
P-glycoprotein inhibitior - 0.8347 83.47%
P-glycoprotein substrate - 0.6991 69.91%
CYP3A4 substrate + 0.5839 58.39%
CYP2C9 substrate - 0.8216 82.16%
CYP2D6 substrate + 0.6215 62.15%
CYP3A4 inhibition + 0.5242 52.42%
CYP2C9 inhibition - 0.8569 85.69%
CYP2C19 inhibition - 0.5508 55.08%
CYP2D6 inhibition + 0.6539 65.39%
CYP1A2 inhibition + 0.6365 63.65%
CYP2C8 inhibition + 0.5134 51.34%
CYP inhibitory promiscuity + 0.5656 56.56%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6052 60.52%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.8471 84.71%
Skin irritation - 0.7289 72.89%
Skin corrosion - 0.9375 93.75%
Ames mutagenesis + 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4499 44.99%
Micronuclear + 0.5200 52.00%
Hepatotoxicity - 0.7083 70.83%
skin sensitisation - 0.8314 83.14%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.6637 66.37%
Acute Oral Toxicity (c) III 0.5742 57.42%
Estrogen receptor binding + 0.7958 79.58%
Androgen receptor binding - 0.5655 56.55%
Thyroid receptor binding + 0.7170 71.70%
Glucocorticoid receptor binding + 0.6725 67.25%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.8228 82.28%
Honey bee toxicity - 0.7824 78.24%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5449 54.49%
Fish aquatic toxicity - 0.5000 50.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 25118.9 nM
Potency
via CMAUP
CHEMBL3577 P00352 Aldehyde dehydrogenase 1A1 35481.3 nM
Potency
via CMAUP
CHEMBL2392 P06746 DNA polymerase beta 39810.7 nM
Potency
via CMAUP
CHEMBL5514 P42858 Huntingtin 35481.3 nM
Potency
via CMAUP
CHEMBL4361 Q07820 Induced myeloid leukemia cell differentiation protein Mcl-1 5612.2 nM
IC50
via CMAUP
CHEMBL1287622 Q9Y468 Lethal(3)malignant brain tumor-like protein 1 35481.3 nM
Potency
via CMAUP
CHEMBL1293226 B2RXH2 Lysine-specific demethylase 4D-like 14125.4 nM
Potency
via CMAUP
CHEMBL1293224 P10636 Microtubule-associated protein tau 22387.2 nM
14125.4 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL1293235 P02545 Prelamin-A/C 11220.2 nM
Potency
via CMAUP
CHEMBL1293232 Q16637 Survival motor neuron protein 56.2 nM
56.2 nM
Potency
Potency
via Super-PRED
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.73% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.42% 96.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 96.30% 96.77%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.04% 97.09%
CHEMBL3231 Q13464 Rho-associated protein kinase 1 93.54% 95.55%
CHEMBL3192 Q9BY41 Histone deacetylase 8 92.27% 93.99%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 91.72% 82.67%
CHEMBL3438 Q05513 Protein kinase C zeta 91.50% 88.48%
CHEMBL241 Q14432 Phosphodiesterase 3A 91.49% 92.94%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 91.45% 92.62%
CHEMBL1951 P21397 Monoamine oxidase A 91.26% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.10% 86.33%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 90.96% 91.79%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.63% 95.89%
CHEMBL4208 P20618 Proteasome component C5 89.45% 90.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 89.25% 96.21%
CHEMBL2581 P07339 Cathepsin D 88.45% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.41% 94.45%
CHEMBL213 P08588 Beta-1 adrenergic receptor 86.98% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.81% 94.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.35% 100.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.54% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.47% 89.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 84.86% 96.95%
CHEMBL2535 P11166 Glucose transporter 83.86% 98.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.24% 95.56%
CHEMBL4247 Q9UM73 ALK tyrosine kinase receptor 82.21% 96.86%
CHEMBL4225 P49760 Dual specificity protein kinase CLK2 81.92% 80.96%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 81.71% 95.78%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 80.34% 89.62%

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.
Annona glabra
Laurus nobilis

Cross-Links

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PubChem 11957301
NPASS NPC312918
ChEMBL CHEMBL1588263
LOTUS LTS0223874
wikiData Q27138971