(S)-autumnaline

Details

Top
Internal ID b35112a0-6365-4b1e-9c35-424f80bf0178
Taxonomy Alkaloids and derivatives > Phenethylisoquinoline alkaloids
IUPAC Name (1S)-1-[2-(3-hydroxy-4,5-dimethoxyphenyl)ethyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
SMILES (Canonical) CN1CCC2=CC(=C(C=C2C1CCC3=CC(=C(C(=C3)OC)OC)O)O)OC
SMILES (Isomeric) CN1CCC2=CC(=C(C=C2[C@@H]1CCC3=CC(=C(C(=C3)OC)OC)O)O)OC
InChI InChI=1S/C21H27NO5/c1-22-8-7-14-11-19(25-2)17(23)12-15(14)16(22)6-5-13-9-18(24)21(27-4)20(10-13)26-3/h9-12,16,23-24H,5-8H2,1-4H3/t16-/m0/s1
InChI Key GZUNPCNPOLOTLX-INIZCTEOSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C21H27NO5
Molecular Weight 373.40 g/mol
Exact Mass 373.18892296 g/mol
Topological Polar Surface Area (TPSA) 71.40 Ų
XlogP 3.30
Atomic LogP (AlogP) 3.29
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

Top
23068-65-7
(1S)-1-[2-(3-hydroxy-4,5-dimethoxyphenyl)ethyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Autumnaline
CHEBI:80672
DTXSID50551719
Q27149714
(1S)-1-[2-(3-Hydroxy-4,5-dimethoxyphenyl)ethyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

2D Structure

Top
2D Structure of (S)-autumnaline

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6918 69.18%
Caco-2 + 0.8218 82.18%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.5685 56.85%
OATP2B1 inhibitior - 0.8585 85.85%
OATP1B1 inhibitior + 0.9232 92.32%
OATP1B3 inhibitior + 0.9320 93.20%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.5643 56.43%
P-glycoprotein inhibitior + 0.6655 66.55%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6514 65.14%
CYP2C9 substrate + 0.7825 78.25%
CYP2D6 substrate + 0.8432 84.32%
CYP3A4 inhibition - 0.9239 92.39%
CYP2C9 inhibition - 0.9360 93.60%
CYP2C19 inhibition - 0.9134 91.34%
CYP2D6 inhibition + 0.6083 60.83%
CYP1A2 inhibition + 0.6629 66.29%
CYP2C8 inhibition - 0.5599 55.99%
CYP inhibitory promiscuity - 0.9113 91.13%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6969 69.69%
Eye corrosion - 0.9928 99.28%
Eye irritation - 0.9721 97.21%
Skin irritation - 0.7868 78.68%
Skin corrosion - 0.9377 93.77%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7695 76.95%
Micronuclear - 0.5800 58.00%
Hepatotoxicity - 0.8375 83.75%
skin sensitisation - 0.8921 89.21%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.9255 92.55%
Acute Oral Toxicity (c) III 0.6785 67.85%
Estrogen receptor binding + 0.7788 77.88%
Androgen receptor binding - 0.6607 66.07%
Thyroid receptor binding + 0.7640 76.40%
Glucocorticoid receptor binding + 0.6808 68.08%
Aromatase binding + 0.5245 52.45%
PPAR gamma + 0.6656 66.56%
Honey bee toxicity - 0.8520 85.20%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.8936 89.36%

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 99.41% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.71% 85.14%
CHEMBL261 P00915 Carbonic anhydrase I 95.51% 96.76%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 92.12% 95.89%
CHEMBL2581 P07339 Cathepsin D 91.88% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.17% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.15% 91.11%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.51% 99.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.21% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.01% 86.33%
CHEMBL4208 P20618 Proteasome component C5 86.41% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.49% 95.89%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 85.05% 95.17%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.79% 94.00%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 84.05% 93.40%
CHEMBL2535 P11166 Glucose transporter 83.89% 98.75%
CHEMBL241 Q14432 Phosphodiesterase 3A 82.77% 92.94%
CHEMBL3192 Q9BY41 Histone deacetylase 8 82.47% 93.99%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.98% 92.62%
CHEMBL2056 P21728 Dopamine D1 receptor 81.38% 91.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.10% 95.56%
CHEMBL3820 P35557 Hexokinase type IV 80.75% 91.96%
CHEMBL217 P14416 Dopamine D2 receptor 80.60% 95.62%
CHEMBL5747 Q92793 CREB-binding protein 80.57% 95.12%

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.
Colchicum autumnale
Colchicum ritchiei
Colchicum schimperi

Cross-Links

Top
PubChem 13878324
LOTUS LTS0108773
wikiData Q27149714