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(1R,11R,13S)-16,17-dimethoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.02,10.05,9.014,19]docosa-2(10),3,5(9),14,16,18-hexaen-11-ol

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 7bb4d18e-9fca-4b9b-a2e0-1fa4b15faa6c
Taxonomy Alkaloids and derivatives > Rhoeadine alkaloids
IUPAC Name (1R,11R,13S)-16,17-dimethoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.02,10.05,9.014,19]docosa-2(10),3,5(9),14,16,18-hexaen-11-ol
SMILES (Canonical) CN1CCC2=CC(=C(C=C2C3C1C4=C(C(O3)O)C5=C(C=C4)OCO5)OC)OC
SMILES (Isomeric) CN1CCC2=CC(=C(C=C2[C@H]3[C@H]1C4=C([C@@H](O3)O)C5=C(C=C4)OCO5)OC)OC
InChI InChI=1S/C21H23NO6/c1-22-7-6-11-8-15(24-2)16(25-3)9-13(11)19-18(22)12-4-5-14-20(27-10-26-14)17(12)21(23)28-19/h4-5,8-9,18-19,21,23H,6-7,10H2,1-3H3/t18-,19+,21-/m1/s1
InChI Key XYWRZQQANNOTTD-SVFBPWRDSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H23NO6
Molecular Weight 385.40 g/mol
Exact Mass 385.15253745 g/mol
Topological Polar Surface Area (TPSA) 69.60 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.72
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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2255-44-9
(5bR,12bS,14R)-5b,6,7,8,12b,14-Hexahydro-10,11-dimethoxy-6-methyl-1,3-dioxolo[7,8][2]benzopyrano[3,4-a][3]benzazepin-14-ol

2D Structure

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2D Structure of (1R,11R,13S)-16,17-dimethoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.02,10.05,9.014,19]docosa-2(10),3,5(9),14,16,18-hexaen-11-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8249 82.49%
Caco-2 + 0.8609 86.09%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Lysosomes 0.4730 47.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9224 92.24%
OATP1B3 inhibitior + 0.9464 94.64%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.6467 64.67%
P-glycoprotein inhibitior + 0.6930 69.30%
P-glycoprotein substrate - 0.5918 59.18%
CYP3A4 substrate + 0.6511 65.11%
CYP2C9 substrate - 0.6106 61.06%
CYP2D6 substrate + 0.6661 66.61%
CYP3A4 inhibition - 0.6341 63.41%
CYP2C9 inhibition - 0.5136 51.36%
CYP2C19 inhibition + 0.6113 61.13%
CYP2D6 inhibition - 0.7176 71.76%
CYP1A2 inhibition - 0.8713 87.13%
CYP2C8 inhibition - 0.7453 74.53%
CYP inhibitory promiscuity - 0.7664 76.64%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5846 58.46%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.9628 96.28%
Skin irritation - 0.7904 79.04%
Skin corrosion - 0.9384 93.84%
Ames mutagenesis + 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4706 47.06%
Micronuclear + 0.5200 52.00%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.8609 86.09%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.8098 80.98%
Acute Oral Toxicity (c) III 0.7310 73.10%
Estrogen receptor binding + 0.6020 60.20%
Androgen receptor binding + 0.5635 56.35%
Thyroid receptor binding + 0.6476 64.76%
Glucocorticoid receptor binding + 0.7772 77.72%
Aromatase binding - 0.7644 76.44%
PPAR gamma + 0.7190 71.90%
Honey bee toxicity - 0.8580 85.80%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.7200 72.00%
Fish aquatic toxicity + 0.6603 66.03%

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 99.11% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.21% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.49% 86.33%
CHEMBL2581 P07339 Cathepsin D 94.04% 98.95%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 93.44% 96.77%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 92.48% 82.67%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.12% 85.14%
CHEMBL3192 Q9BY41 Histone deacetylase 8 90.82% 93.99%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 90.66% 93.40%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.43% 92.62%
CHEMBL2056 P21728 Dopamine D1 receptor 89.37% 91.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.09% 91.11%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.98% 95.89%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 86.46% 89.62%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.71% 95.89%
CHEMBL2535 P11166 Glucose transporter 84.25% 98.75%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 84.11% 90.95%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.67% 92.94%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 83.54% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.11% 94.00%
CHEMBL4208 P20618 Proteasome component C5 81.77% 90.00%
CHEMBL3820 P35557 Hexokinase type IV 81.54% 91.96%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 81.34% 96.39%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.18% 97.14%
CHEMBL2413 P32246 C-C chemokine receptor type 1 80.04% 89.50%

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.
Papaver persicum subsp. tauricola
Papaver rhoeas

Cross-Links

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PubChem 12310225
LOTUS LTS0107716
wikiData Q105344721