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Auricularine

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 517ffc22-e237-45d1-8bba-a2a4a3828186
Taxonomy Organoheterocyclic compounds > Indoles and derivatives > Pyrroloindoles
IUPAC Name N,N-dimethyl-2-[2-[(1S,9R,10S,15R,16R)-12,14,14,19-tetramethyl-8,19-diazapentacyclo[7.7.3.01,9.02,7.010,15]nonadeca-2,4,6,11-tetraen-16-yl]-1H-indol-3-yl]ethanamine
SMILES (Canonical) CC1=CC2C(C(C34C2(NC5=CC=CC=C53)N(CC4)C)C6=C(C7=CC=CC=C7N6)CCN(C)C)C(C1)(C)C
SMILES (Isomeric) CC1=C[C@H]2[C@@H]([C@H]([C@]34[C@]2(NC5=CC=CC=C53)N(CC4)C)C6=C(C7=CC=CC=C7N6)CCN(C)C)C(C1)(C)C
InChI InChI=1S/C33H42N4/c1-21-19-25-28(31(2,3)20-21)29(30-23(15-17-36(4)5)22-11-7-9-13-26(22)34-30)32-16-18-37(6)33(25,32)35-27-14-10-8-12-24(27)32/h7-14,19,25,28-29,34-35H,15-18,20H2,1-6H3/t25-,28-,29-,32+,33+/m0/s1
InChI Key RTHNIWHULJBNTJ-BXFVMDGOSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C33H42N4
Molecular Weight 494.70 g/mol
Exact Mass 494.34094736 g/mol
Topological Polar Surface Area (TPSA) 34.30 Ų
XlogP 6.20
Atomic LogP (AlogP) 6.37
H-Bond Acceptor 3
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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73706-32-8
C09043
N,N-dimethyl-2-[2-[(1S,9R,10S,15R,16R)-12,14,14,19-tetramethyl-8,19-diazapentacyclo[7.7.3.01,9.02,7.010,15]nonadeca-2,4,6,11-tetraen-16-yl]-1H-indol-3-yl]ethanamine
AC1L9C25
CHEBI:2927
CHEMBL4165417
DTXSID40331704
Q27105884

2D Structure

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2D Structure of Auricularine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9832 98.32%
Caco-2 - 0.5911 59.11%
Blood Brain Barrier + 0.9250 92.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Nucleus 0.5549 55.49%
OATP2B1 inhibitior - 0.8547 85.47%
OATP1B1 inhibitior + 0.7850 78.50%
OATP1B3 inhibitior + 0.9384 93.84%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior + 0.5471 54.71%
BSEP inhibitior + 0.9916 99.16%
P-glycoprotein inhibitior + 0.9357 93.57%
P-glycoprotein substrate + 0.7814 78.14%
CYP3A4 substrate + 0.7576 75.76%
CYP2C9 substrate - 0.7919 79.19%
CYP2D6 substrate + 0.4511 45.11%
CYP3A4 inhibition - 0.5905 59.05%
CYP2C9 inhibition - 0.7350 73.50%
CYP2C19 inhibition - 0.6802 68.02%
CYP2D6 inhibition - 0.6291 62.91%
CYP1A2 inhibition + 0.5421 54.21%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity + 0.8017 80.17%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6263 62.63%
Eye corrosion - 0.9889 98.89%
Eye irritation - 0.9667 96.67%
Skin irritation - 0.7592 75.92%
Skin corrosion - 0.9000 90.00%
Ames mutagenesis + 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.9732 97.32%
Micronuclear + 0.5300 53.00%
Hepatotoxicity - 0.8539 85.39%
skin sensitisation - 0.8196 81.96%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.9375 93.75%
Nephrotoxicity - 0.8889 88.89%
Acute Oral Toxicity (c) III 0.5387 53.87%
Estrogen receptor binding + 0.7696 76.96%
Androgen receptor binding + 0.7520 75.20%
Thyroid receptor binding + 0.7448 74.48%
Glucocorticoid receptor binding + 0.6650 66.50%
Aromatase binding + 0.7034 70.34%
PPAR gamma + 0.7330 73.30%
Honey bee toxicity - 0.7018 70.18%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.5900 59.00%
Fish aquatic toxicity + 0.9763 97.63%

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
CHEMBL1914 P06276 Butyrylcholinesterase 99.21% 95.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.01% 96.09%
CHEMBL233 P35372 Mu opioid receptor 98.07% 97.93%
CHEMBL2581 P07339 Cathepsin D 97.86% 98.95%
CHEMBL1937 Q92769 Histone deacetylase 2 97.43% 94.75%
CHEMBL3524 P56524 Histone deacetylase 4 96.21% 92.97%
CHEMBL3155 P34969 Serotonin 7 (5-HT7) receptor 95.89% 90.71%
CHEMBL228 P31645 Serotonin transporter 95.43% 95.51%
CHEMBL240 Q12809 HERG 94.89% 89.76%
CHEMBL4145 Q9UKV0 Histone deacetylase 9 94.79% 85.49%
CHEMBL3310 Q96DB2 Histone deacetylase 11 94.58% 88.56%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.54% 95.56%
CHEMBL3192 Q9BY41 Histone deacetylase 8 94.31% 93.99%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 91.49% 93.40%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 91.07% 94.62%
CHEMBL5103 Q969S8 Histone deacetylase 10 90.67% 90.08%
CHEMBL5805 Q9NR97 Toll-like receptor 8 90.36% 96.25%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 90.09% 97.50%
CHEMBL255 P29275 Adenosine A2b receptor 89.77% 98.59%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.39% 91.11%
CHEMBL220 P22303 Acetylcholinesterase 86.85% 94.45%
CHEMBL2096618 P11274 Bcr/Abl fusion protein 86.03% 85.83%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 85.31% 89.44%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 84.84% 95.17%
CHEMBL4302 P08183 P-glycoprotein 1 84.64% 92.98%
CHEMBL5493 O15552 Free fatty acid receptor 2 84.01% 92.86%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.42% 89.00%
CHEMBL5028 O14672 ADAM10 83.35% 97.50%
CHEMBL202 P00374 Dihydrofolate reductase 80.91% 89.92%
CHEMBL4208 P20618 Proteasome component C5 80.90% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.86% 95.89%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 80.82% 96.39%
CHEMBL3902 P09211 Glutathione S-transferase Pi 80.60% 93.81%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.48% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.47% 86.33%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 80.04% 96.67%

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.
Exallage auricularia
Millettia extensa

Cross-Links

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PubChem 441990
LOTUS LTS0097018
wikiData Q27105884