(2R,3R,13bS)-2-methoxy-2,3,5,6,8,9-hexahydro-1H-indolo[7a,1-a]isoquinoline-3,12-diol

Details

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Internal ID 54b4ee38-b2b6-4b14-a121-138fdf36c67f
Taxonomy Alkaloids and derivatives > Erythrina alkaloids > Erythrinanes
IUPAC Name (2R,3R,13bS)-2-methoxy-2,3,5,6,8,9-hexahydro-1H-indolo[7a,1-a]isoquinoline-3,12-diol
SMILES (Canonical) COC1CC23C(=CC1O)CCN2CCC4=C3C=C(C=C4)O
SMILES (Isomeric) CO[C@@H]1C[C@@]23C(=C[C@H]1O)CCN2CCC4=C3C=C(C=C4)O
InChI InChI=1S/C17H21NO3/c1-21-16-10-17-12(8-15(16)20)5-7-18(17)6-4-11-2-3-13(19)9-14(11)17/h2-3,8-9,15-16,19-20H,4-7,10H2,1H3/t15-,16-,17+/m1/s1
InChI Key MHLIDZIIDGSODK-ZACQAIPSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C17H21NO3
Molecular Weight 287.35 g/mol
Exact Mass 287.15214353 g/mol
Topological Polar Surface Area (TPSA) 52.90 Ų
XlogP 0.90
Atomic LogP (AlogP) 1.56
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3R,13bS)-2-methoxy-2,3,5,6,8,9-hexahydro-1H-indolo[7a,1-a]isoquinoline-3,12-diol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9924 99.24%
Caco-2 + 0.7851 78.51%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.8176 81.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8758 87.58%
OATP1B3 inhibitior + 0.9503 95.03%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior - 0.4858 48.58%
P-glycoprotein inhibitior - 0.8845 88.45%
P-glycoprotein substrate + 0.5448 54.48%
CYP3A4 substrate + 0.6247 62.47%
CYP2C9 substrate - 0.6124 61.24%
CYP2D6 substrate + 0.6678 66.78%
CYP3A4 inhibition - 0.9114 91.14%
CYP2C9 inhibition - 0.8442 84.42%
CYP2C19 inhibition - 0.7000 70.00%
CYP2D6 inhibition + 0.6299 62.99%
CYP1A2 inhibition - 0.6040 60.40%
CYP2C8 inhibition - 0.7103 71.03%
CYP inhibitory promiscuity - 0.7458 74.58%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5314 53.14%
Eye corrosion - 0.9889 98.89%
Eye irritation - 0.9434 94.34%
Skin irritation - 0.7344 73.44%
Skin corrosion - 0.9226 92.26%
Ames mutagenesis - 0.6944 69.44%
Human Ether-a-go-go-Related Gene inhibition - 0.3998 39.98%
Micronuclear + 0.5700 57.00%
Hepatotoxicity - 0.5830 58.30%
skin sensitisation - 0.8271 82.71%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9875 98.75%
Nephrotoxicity - 0.7257 72.57%
Acute Oral Toxicity (c) II 0.4322 43.22%
Estrogen receptor binding + 0.5551 55.51%
Androgen receptor binding + 0.7080 70.80%
Thyroid receptor binding + 0.6236 62.36%
Glucocorticoid receptor binding + 0.6174 61.74%
Aromatase binding - 0.6190 61.90%
PPAR gamma - 0.5077 50.77%
Honey bee toxicity - 0.8405 84.05%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6800 68.00%
Fish aquatic toxicity + 0.7910 79.10%

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 98.51% 96.09%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 92.54% 93.40%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.49% 91.11%
CHEMBL241 Q14432 Phosphodiesterase 3A 91.53% 92.94%
CHEMBL2581 P07339 Cathepsin D 89.81% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.41% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.28% 85.14%
CHEMBL4208 P20618 Proteasome component C5 88.64% 90.00%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 88.49% 93.10%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.19% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.12% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.69% 86.33%
CHEMBL4040 P28482 MAP kinase ERK2 84.18% 83.82%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.05% 94.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.95% 95.89%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 82.37% 91.03%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.63% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.44% 97.09%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 81.33% 85.00%
CHEMBL2056 P21728 Dopamine D1 receptor 80.03% 91.00%

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.
Cocculus laurifolius

Cross-Links

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PubChem 162949024
LOTUS LTS0005995
wikiData Q105163858