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16-hydroxy-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-10-azapentacyclo[9.7.1.02,6.08,19.013,18]nonadeca-1(18),2(6),7,11(19),12,14,16-heptaen-9-one

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 d1fc3949-2243-47ea-a2f8-859284e14f64
Taxonomy Alkaloids and derivatives > Aristolactams
IUPAC Name 16-hydroxy-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-10-azapentacyclo[9.7.1.02,6.08,19.013,18]nonadeca-1(18),2(6),7,11(19),12,14,16-heptaen-9-one
SMILES (Canonical) C1OC2=C(O1)C3=C4C=C(C=CC4=CC5=C3C(=C2)C(=O)N5C6C(C(C(C(O6)CO)O)O)O)O
SMILES (Isomeric) C1OC2=C(O1)C3=C4C=C(C=CC4=CC5=C3C(=C2)C(=O)N5[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
InChI InChI=1S/C22H19NO9/c24-6-14-17(26)18(27)19(28)22(32-14)23-12-3-8-1-2-9(25)4-10(8)16-15(12)11(21(23)29)5-13-20(16)31-7-30-13/h1-5,14,17-19,22,24-28H,6-7H2/t14-,17-,18+,19-,22-/m1/s1
InChI Key LJQXKFYPXDAXBL-MAEOEUOPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H19NO9
Molecular Weight 441.40 g/mol
Exact Mass 441.10598118 g/mol
Topological Polar Surface Area (TPSA) 149.00 Ų
XlogP 0.80
Atomic LogP (AlogP) 0.19
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 2

Synonyms

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Aristolactam IIIa N-??-glucoside
AKOS040763176
10-Hydroxy-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-cd]benzo[f]indol-5(6H)-one

2D Structure

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2D Structure of 16-hydroxy-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,5-dioxa-10-azapentacyclo[9.7.1.02,6.08,19.013,18]nonadeca-1(18),2(6),7,11(19),12,14,16-heptaen-9-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6427 64.27%
Caco-2 - 0.8066 80.66%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Nucleus 0.5427 54.27%
OATP2B1 inhibitior - 0.5662 56.62%
OATP1B1 inhibitior + 0.8568 85.68%
OATP1B3 inhibitior + 0.9403 94.03%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.5848 58.48%
P-glycoprotein inhibitior - 0.6181 61.81%
P-glycoprotein substrate - 0.7069 70.69%
CYP3A4 substrate + 0.6033 60.33%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8498 84.98%
CYP3A4 inhibition - 0.7993 79.93%
CYP2C9 inhibition - 0.8873 88.73%
CYP2C19 inhibition - 0.8645 86.45%
CYP2D6 inhibition - 0.8408 84.08%
CYP1A2 inhibition - 0.7364 73.64%
CYP2C8 inhibition - 0.5570 55.70%
CYP inhibitory promiscuity - 0.6750 67.50%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.5591 55.91%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.8954 89.54%
Skin irritation - 0.7788 77.88%
Skin corrosion - 0.9382 93.82%
Ames mutagenesis + 0.5256 52.56%
Human Ether-a-go-go-Related Gene inhibition - 0.4007 40.07%
Micronuclear + 0.9300 93.00%
Hepatotoxicity + 0.5408 54.08%
skin sensitisation - 0.8639 86.39%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.5969 59.69%
Acute Oral Toxicity (c) III 0.4840 48.40%
Estrogen receptor binding + 0.5403 54.03%
Androgen receptor binding + 0.5858 58.58%
Thyroid receptor binding - 0.5415 54.15%
Glucocorticoid receptor binding + 0.6504 65.04%
Aromatase binding - 0.5355 53.55%
PPAR gamma + 0.6938 69.38%
Honey bee toxicity - 0.8319 83.19%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.6855 68.55%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.27% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.71% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.59% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.42% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.79% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.59% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.98% 97.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 89.60% 96.77%
CHEMBL2140 P48775 Tryptophan 2,3-dioxygenase 88.80% 98.46%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.02% 94.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.70% 100.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 87.14% 89.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.80% 99.23%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 85.96% 95.83%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.31% 86.33%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 84.34% 93.10%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.11% 92.62%
CHEMBL3384 Q16512 Protein kinase N1 83.34% 80.71%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 82.47% 93.40%

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.
Aristolochia pubescens

Cross-Links

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PubChem 5319621
LOTUS LTS0045029
wikiData Q105152732