Codeine N-oxide

Details

Top
Internal ID 84be3565-7bfd-45ae-bd77-b1f3eb721dba
Taxonomy Alkaloids and derivatives > Morphinans
IUPAC Name (3S,4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-ol
SMILES (Canonical) C[N+]1(CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O)[O-]
SMILES (Isomeric) C[N@@+]1(CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O)[O-]
InChI InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-,19-/m0/s1
InChI Key BDLSDHWCOJPHIE-KFUGMXNISA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C18H21NO4
Molecular Weight 315.40 g/mol
Exact Mass 315.14705815 g/mol
Topological Polar Surface Area (TPSA) 56.80 Ų
XlogP 0.60
Atomic LogP (AlogP) 1.51
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

Top
Codeine-N-oxide
Codeigene
3688-65-1
Genocodein
Genocodeine
EINECS 222-988-4
(3S,4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-3-oxido-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-ol
Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, 17-oxide, (5-alpha,6-alpha)-
UNII-Z32OFX7V17
DTXSID00190359
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top
2D Structure of Codeine N-oxide

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5685 56.85%
Caco-2 + 0.8228 82.28%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.3424 34.24%
OATP2B1 inhibitior - 0.8602 86.02%
OATP1B1 inhibitior + 0.9216 92.16%
OATP1B3 inhibitior + 0.9394 93.94%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.7840 78.40%
P-glycoprotein inhibitior - 0.8714 87.14%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6721 67.21%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7117 71.17%
CYP3A4 inhibition - 0.8591 85.91%
CYP2C9 inhibition - 0.8429 84.29%
CYP2C19 inhibition - 0.7613 76.13%
CYP2D6 inhibition - 0.7587 75.87%
CYP1A2 inhibition - 0.8243 82.43%
CYP2C8 inhibition - 0.7706 77.06%
CYP inhibitory promiscuity - 0.9033 90.33%
UGT catelyzed + 1.0000 100.00%
Carcinogenicity (binary) - 0.8800 88.00%
Carcinogenicity (trinary) Non-required 0.5574 55.74%
Eye corrosion - 0.9826 98.26%
Eye irritation - 0.9820 98.20%
Skin irritation - 0.7705 77.05%
Skin corrosion - 0.9267 92.67%
Ames mutagenesis - 0.7200 72.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5631 56.31%
Micronuclear - 0.5700 57.00%
Hepatotoxicity - 0.6299 62.99%
skin sensitisation - 0.8222 82.22%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9500 95.00%
Nephrotoxicity - 0.7820 78.20%
Acute Oral Toxicity (c) III 0.7004 70.04%
Estrogen receptor binding - 0.7097 70.97%
Androgen receptor binding - 0.6562 65.62%
Thyroid receptor binding + 0.5781 57.81%
Glucocorticoid receptor binding - 0.5000 50.00%
Aromatase binding - 0.7579 75.79%
PPAR gamma - 0.6122 61.22%
Honey bee toxicity - 0.7437 74.37%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.8657 86.57%

Targets

Top

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 98.07% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.07% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.53% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.10% 95.89%
CHEMBL3192 Q9BY41 Histone deacetylase 8 88.56% 93.99%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.71% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.33% 94.00%
CHEMBL2535 P11166 Glucose transporter 86.47% 98.75%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 83.63% 91.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.43% 97.14%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 81.76% 89.05%
CHEMBL1255126 O15151 Protein Mdm4 80.45% 90.20%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.06% 97.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.03% 92.94%

Plants that contains it

Top
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.
Aloe microstigma
Chrozophora plicata
Papaver somniferum

Cross-Links

Top
PubChem 5359929
NPASS NPC45955